Department of Chemistry Annual Report 2019

Scan the QR-code and read more at kemi.dtu.dk

DTU Technical University of Denmark

Department of Chemistry Kemitorvet Building 207 DK-2800 Kgs. Lyngby

kemi.dtu.dk Picture: Greg Stewart/SLAC A well-tuned Department

The DTU Chemistry Management Group (left to right) Lise Peitersen, Erling H. Stenby, Jens O. Duus, Inge Holkmann Olsen, and Klaus B. Møller.

Content Welcome to the DTU Chemistry Annual Report In 2019, the researchers of DTU Chemistry and we are glad to present some of these expanded by approximately 12 % to 66 new 2019 – a year characterized by innovation, were very productive. The number of researchers as seminar speakers. These students in 2019. 3 Welcome evaluation, and academic excellence. Peer-Reviewed articles (228) rose by 30 % inspiring talks are fueling new ideas at the 4 Faculty: Synergy as compared to 2018. Three very promising Department. In 2019, a record number of 26 PhD students a driving force In the fall, an international research evaluation patents were obtained and currently, we began their research at the Department 6 Recruiting enzymes for panel consisting of four international have 28 ongoing patent-cases. In addition, Significant external funding has once again while 17 graduated. It is inspiring to see how new tasks in chemistry researchers visited the Department to scruti­nize several DTU Chemistry spin-out companies strengthened our research groups with productive our PhD school is. Our research our activities. The overall feedback was very are flourishing with new investments and talents from Denmark and abroad. It has also groups benefit vastly from the curiosity 8 A peek into the molecular positive. Especially our ‘translational research’ partnerships. made new projects possible and even new and dedication of our PhD students, who engine room – basic research that industry and society infrastructures. In 2020, the construction of are closely supervised by our faculty. The 10 A novel approach to treatment can easily benefit from – impressed the panel. The Department takes great pride in the screening platform DTU SCore will begin PhD school assists the development of these of Rheumatoid Arthritis Since translational research is a core part of contributing to important, groundbreaking thanks to a 10.6 MDKK grant from the Novo young scientists through power performance 12 Smart chemistry to save vast the ‘DTU-dna’, we are very pleased with the research networks. Thus, I am excited to Nordisk Foundation. The new infrastructure courses, writing workshops, participation amounts of CO2 panel’s focus on this area as a clear strength. see several researchers at DTU Chemistry at DTU Chemistry will – combined with the in international conferences, and close being a part of government-designated DK-OPENSCREEN platform – be a unique collaboration with the industry. Exclusive 14 Shedding Light on Molecular In conclusion, the panel also highlighted the ESS Lighthouse environments. The PIPPI- university based high-throughput screening PhD-alliances between universities, such Recognition Mechanisms successful recruitment of talented faculty consortium is currently in its final phase. platform in Denmark and serve as a starting as EuroTech and Nordic Five Tech, are 16 PhD from DTU Chemistry in recent years as an important part of the Through several years, the project, well repre- point for chemical biology research and early enhancing the Department’s synergy and 26 Master Theses 2019 positive path the Department is moving on. sented by members of the DTU Chemistry drug discovery. collaboration with other excellent research 27 Publications During the visit, the panel followed a well­ ‘protein squad’, has thoroughly investigated institutions. planned schedule to get a full insight into e.g. protein-protein interactions in relation Once again, we had a record year in the 28 Events our research – e.g. through meetings with all to product formulations. The exciting work uptake of new students, which shows that All in all, 2019 has been a very productive 30 Highlights 2019 research areas. A poster session by the PhD done by the consortium forms a great both ‘Chemistry and Technology’ and year in all areas of the Department. We are 33 Key numbers students added another dimension to this starting point for future protein projects. ‘Human Life Science Engineering’ are popular definitely on an exciting track and doing 34 Acknowledgement insight. In the evaluation report, the panel choices amongst the new generation of bright well on projects that is part of our core dna. 36 Staff pointed out potential areas of improvement Our researchers and advanced infrastructure engineers. ‘Chemistry and Technology’ I hope you will enjoy this report. and suggestions on how to fulfil new goals. are in growing demand. Researchers and enrolled 88 students and ‘Human Life Science This has inspired new ideas for the future companies from all over the world are Engineering’ 60 students. Furthermore, Erling H. Stenby departmental strategy. reaching out to us for closer collaboration the MSc programme, Applied Chemistry, Head of Department

2 3 ANNUAL REPORT 2019 RESEARCH AREAS

Faculty: Synergy as a driving force

The research groups work effectively together across expertises, which gives a synergy effect to research at the Department. That is the conclusion from the Heads of Sections at the Department and an external evaluation panel.

"It has been an extremely productive and favourable year," says chemical substances. According to Head of Section Jens Ø. Duus, Professor Klaus B. Møller, Head of Section of Physical and Mogens has brought strong analytical skills. Biophysical Chemistry at DTU Chemistry. The section of Physical and Biophysical Chemistry now has Professor Head of Section of Organic and Inorganic Chemistry, Professor Kristoffer Almdal in the fold. He is interested in polymers as a class of Jens Ø. Duus, continues: materials. From a fundamental perspective, he is strong on subjects such as the development of polymer synthesis methods, the physics “We see a faculty that has been supported for its projects by private of polymer melts and solutions, and especially self-organization Physical and Biophysical Chemistry: foundations. This really strengthens the research at the department”. phenomena. From a more applied aspect, he does research on func- Sections Günther H. J. Peters, Wei Yan, Irene Shim, tional polymeric nanoparticles and sensors, polymeric biomaterials, Niels Engholm Henriksen, René Wugt Larsen, In particular, the fields of biological chemistry and supramolecular polymer degradation, adhesion, and interfaces in polymer composites. Organic and Inorganic Chemistry Klaus B. Møller, Esben Thormann, Kasper chemistry have received a financial boost, but the Heads of Sections The Section of Organic and Inorganic Chemistry Planeta Kepp, Sonia Coriani, Kristoffer Almdal, Pernille Harris, and Kenny Ståhl. say that all research groups have positioned themselves very strongly “Kristoffer is a huge capacity in the field of polymers and materials. comprises activities within Catalysis and Sustainable in recent time. With him and e.g. Professor Esben Thormann we are somewhat of Chemistry, Materials Chemistry, and Organic Chemistry. a powerhouse in the field of research, and it has positioned us very Common themes are the synthesis and characterization In the fall of 2019, DTU Chemistry went through a comprehensive well when it comes to both basic research and research aimed at the of small to very large inorganic and organic molecules. research evaluation and the department was awarded "a very high industry,” says Professor Klaus B. Møller. The research areas are homogenous and heterogenous Two new Professors continue grade" by an external evaluation panel of high-profile scientists. catalysis; gas separation and absorption; development of The panel praised the individual strengths of each research group Takes pride in teaching new materials; conversion of biomass; electrochemistry; protein research and great synergy effects across the Department, including the PhD All of Faculty is committed to the education of future chemists and bioelectrochemistry; graphene nanoparticles; coordination school, as well as technology transfer efforts. contributes to this through teaching at a high level. A good example chemistry; chemical biology; NMR spectroscopy. In 2019, long-time faculty members Pernille Harris and Günther is Professor Robert Madsen who won the award as ‘Lecturer of the H. J. Peters were appointed Professors at DTU Chemistry. The two Heads of sections also highlight that faculty, in 2019, year’ at DTU (read more under Highlights pp. 32). Physical and Biophysical Chemistry They will continue research into the properties of proteins, have been very productive in regards to publications – in fact, The Section of Physical and Biophysical Chemistry which is an important field when it comes to developing a record number – and several of these were published in high- As a new initiative DTU introduced evening teaching in 2019 and comprises activities within pure and applied physical sustainable solutions for protein-based pharmaceuticals and impact journals. DTU Chemistry was in the front line with implementation and chemistry. It covers both microscopic atomic-level industrial enzymes. Recently, both Pernille and Günther have successful execution of evening teaching in a core course in physical descriptions and the macroscopic thermodynamic been working on a major pan-European Horizon 2020 project Two new faculty members chemistry, commended by the Dean. approach. Common themes are determination of structure called PIPPI. The aim of the project - which is in its final In connection with the reallocation of faculty from DTU Nanotech, and behaviour of small to medium-sized molecules as phase - is to map the excipients that can make proteins stable, DTU Chemistry received two strong researchers. In addition to daily teaching, DTU Chemistry also takes great well as proteins, and many projects involve spectroscopy, resulting in a database containing raw data with information responsibility for the study management of three of DTU's scattering, and computer modelling. The research on the effects of the excipients and interactions with proteins. Associate Professor Mogens Havsteen Jakobsen joined Organic programmes by having three Heads of Studies. Professor Jens Ø. areas are Biophysical and Biomedicinal Chemistry; IR, In their day-to-day work, Pernille and Günther work closely and Inorganic Chemistry. He has worked with the development Duus is Head of Study of the MSc programme Applied Chemistry, THz, and Raman Spectroscopy; High Pressure Phase together in an iterative process. Where Pernille mainly studies of innovative sensor technologies in environmental, biomedical, Professor Klaus B. Møller of the BSc programme Chemistry and Behaviour for Oil and Gas Production; Protein and X-ray proteins by using of X-ray scattering, light scattering, and other and security applications. Along with him, he brings the invention Technology, and Professor Mads H. Clausen of the BSc programme Crystallography; Polymers and Functional Interfaces; spectroscopic methods, Günther performs calculations and CRIM-TRACK – a digital sniffer dog that can detect various Human Life Science Engineering. Theoretical, Computational, and Femtochemistry. modeling on the computer.

Organic and Inorganic Chemistry: Jens Ø. Duus, David Tanner, Susanne Mossin, Robert Madsen, Charlotte Held Gotfredsen, Søren Kegnæs, Anders Riisager, Rasmus Fehrmann, Jingdong Zhang, Mads H. Clausen, Mogens Havsteen Jakobsen, Kasper Steen Pedersen, Sophie Beeren, Katrine Qvortrup, Luca Laraia, Kira Astakhova, and Martin Nielsen.

4 5 ANNUAL REPORT 2019 ORGANIC AND INORGANIC CHEMISTRY

Recruiting enzymes for new tasks in chemistry

Cyclodextrin glucanotransferase is used to generate a dynamic mixture of cyclodextrins starting from various glucans. Addition of suitable templates induces a change in cyclodextrin distribution.

By combining enzymology with supramolecular chemistry, the generation. Oligosaccharides are particularly they form reversibly and the smaller cyclodextrins The Beeren Group group of Sophie Beeren is paving the way for more sustainable challenging targets. are more stable. Therefore, production of the larger LRCDs has previously been regarded as impractical. Sophie Beeren is Australian. She moved to the United production of chemicals. Biocompatible molecules We have preliminary results showing that it is indeed Kingdom in 2006 to undertake a PhD at the University of for drug delivery possible to stabilize the larger LRCDs by the use of Cambridge. In 2011, she accepted a position as Postdoc The group is currently looking at Large-Ring molecular templates. So far we have been able to at the Carlsberg Laboratory in Copenhagen and went on Enzymes are the biological equivalent of enzymes, which she calls Enzyme-Mediated Cyclodextrins (LRCDs). These are unusual stabilise the formation of LRCDs with up to 10 glucose to become Researcher at DTU Chemistry in 2015, then catalysts in chemical industry: they speed up Dynamic Combinatorial Chemistry: nanoscale macrocyclic oligomers of glucose units.” says Sophie Beeren. Assistant Professor in 2017 and Associate Professor in reactions between other compounds without that are promising as biocompatible and 2019. being consumed in the process. But what if “Normally, an enzyme-catalysed reaction biodegradable hosts for stabilization, delivery Possible applications enzymes could perform the same job in the will be like a one-way street. Starting and release of functional bioactive molecules. in food and pharma In the near future, the group will increase substantially industry? Associate Professor Sophie Beeren with given reactants, the result will be a The “guest molecules” could be drugs, Initially, the group showed that the enzyme in size due to new grants. At the time of writing, the heads efforts at DTU Chemistry in enzyme- single product. The process is kinetically diagnostic markers, flavours or aromas. cyclodextrin glycosyltransferase (CGTase) can be group consists of Sophie Beeren, three PhD Students and based synthesis. controlled. Instead, we propose to used in the presence of artificial molecular templates one Postdoc. Over the coming years, two additional PhD employ enzymes that catalyse reversible Graphic textbook illustrations will show to selectively synthesise the three common small students and three Postdoctoral researchers will be hired. “Organic chemistry can achieve amazing reactions between molecular building cyclodextrins as nice, rigid truncated cone- CDs from α-glucan under thermodynamic control. Sophie Beeren is one of just 28 researchers to receive a things, but does have shortcomings in relation blocks to generate dynamic mixtures shaped molecules, each with an internal Further, synthetic molecular templates are utilised to Carlsberg Foundation Young Researcher Fellowship grant to sustainability,” says Sophie Beeren. of interconverting oligomeric products. cavity able to contain a guest molecule. favour larger LRCDs, which have nine and ten glucose amounting to 4.5 MDKK. The Novo Nordisk Foundation To achieve selective synthesis of specific And indeed, this is true for the smallest units respectively. has also realised the potential and groundbreaking nature Typically, chemical synthesis of complex products, we will exploit artificial molecular and commonly available cyclodextrins α, of Sophie Beeren's research and have awarded a 2.87 molecules requires multiple steps, each templates that bind to, stabilize, and thus β and γ, formed from 6, 7, and 8 glucose “If we can stabilize, isolate and study LRCDs in the MDKK under the funding instrument Biotechnology-based followed by a purification process, and amplify the synthesis of products that monomers each. 15-17 monomer range, I would be more than happy,” Synthesis and Production Research. typically producing various biproducts. we chose. We exploit Nature’s catalyst – says Sophie Beeren. This leads to high costs, energy enzymes – to do chemistry for us, because “Large-ring cyclodextrins, however, are Sophie Beeren has published a long range of scientific consumption, and generation of waste. they are incredibly efficient. But we try to flexible and little explored. We want to While enzyme-mediated production of LRCDs could articles in the Journal of the American Chemical Society convince them to generate different products elucidate their actual structures, and also find applications in the food, pharmaceutical, and (JACS), Angewandte Chemie, and other prestigious “If we can replace some of the traditional in the lab, to those they would normally establish which guests can bind inside cosmetics industries, Sophie Beeren emphasizes that journals. chemical synthesis in industrial production make in biological systems.” them,” says Sophie Beeren. her research is fundamental: with enzyme-mediated processes, we can develop more sustainable processes. Despite the many reasons to prefer enzyme- In the case of LRCDs, there is a clear “Our role is not to develop or optimise processes for This is because enzymatic processes are mediated production over traditional connection between size and functionality. implementation in industry but rather to explore new fast, specific, and take place under mild chemical synthesis, a general transition As the molecule becomes larger, it becomes ideas, and provide novel and creative approaches. conditions,” says Sophie Beeren. could obviously not happen all at once. The more flexible, opening up the possibility to Still, we do find the LRCDs especially interesting, strongest case for the new paradigm can be host and transport larger guest molecules. because they are extremely difficult to access using Molecular templates amplify made for relatively complex molecules. This traditional approaches. Here, we see an area where we synthesis is because the more complex the compound, “Actually, quite large LRCDs are generated will not just suggest a way towards more sustainable The real novelty in the work of Sophie the more steps it will take to produce it by in the enzymatic production of the common production, but also develop new and hopefully useful Beeren is the overall concept, a traditional synthesis – and the larger the cost smaller cyclodextrins, but within minutes materials.” Associate Professor Sophie Beeren non-traditional approach to the use of will be in terms of money, energy, and waste will they degrade into smaller ones, because [email protected]

6 7 ANNUAL REPORT 2019 PHYSICAL AND BIOPHYSICAL CHEMISTRY

Professor Klaus B. Møller and colleagues had precious beam time The Linac Coherent Light Source (LCLS) at Stanford University. A peek into at the European XFEL facility in May 2019.

experiments. It is characteristic of this field Chemistry – has begun exploring a new of molecules is done with ultraviolet light. that you can never rely on experiments alone. type of investigations. Instead of preparing The subsequent study of the ground-state Without simulations, you cannot be sure that samples for excitation studies, they do molecules is done by stroboscopic X-ray what you observe is actually what you think almost the opposite. Here, the laser beam shattering. the molecular you observe,” Klaus B. Møller comments, wavelength is designed to counteract the underlining that the opposite is also true: normal vibration of the molecules. In other Asked about unexpected results from the words, the molecules in this sub-population experiments, Klaus B. Møller replies: “We cannot rely on simulations alone either. stop vibrating. We need experiments to back them up. This “We were surprised by the role of the solvent. is an ongoing interplay.” The magnitude of this achievement is Intuitively, you would assume the presence engine room illustrated by the fact, that an article based of a solvent to facilitate the fast return to The experiments at LCLS are set up by on the project has been published in the top equilibrium, as the solvent introduces more the group of Senior Researcher Kristoffer scientific journal Physical Review Letters. degrees of freedom to the system. However, By combining X-ray scattering “Very often does the occurrence of a ultra-short X-ray pulses that hit the sample Haldrup and Professor Martin M. Nielsen, we saw that the solvent can actually have an at Stanford University and chemical reaction depend on a localized, and elucidate the behaviour of individual DTU Physics, while the computer simulations “We are able to extract these “frozen” adverse effect by blocking internal channels elevated level of energy. So, if we are able molecules in a sample. are mainly done in the group of Klaus B. molecules from our further considerations. used by the molecule to redistribute energy.” computer simulations, to understand how and when energy will Møller at DTU Chemistry. Often numerous What interests us is not this sub-population, DTU researchers are able concentrate in a given area inside a molecule, Using the exact right wavelength, an optical scientists from several countries will be but instead what happens to all the other The molecule studied in the experiments is we may be able to create the right conditions laser is able to create a sub-population of involved. For instance, more than 40 molecules. How will these ground-state “PtPOP”, a model system for photo-catalysis to study how molecules re- for that to take place. This will potentially molecules by excitation. The excitation researchers from a handful of countries are molecules react to the disturbance that studies. One advantage is the relative distribute energy internally. speed up reactions significantly – and this makes these molecules stand out, which credited in recently accepted papers in the we induced?” harmony of this molecule. By selecting a could in principle apply to a multitude of facilitates studying them. prestigious journals Angewandte Chemie molecule that would not snap back into the different reactions.” and Nature Communications. To illustrate, Klaus B. Møller uses original equilibrium too fast, the researchers When disturbed, a chemical system Obtaining beam time at the LCLS is an a metaphor: gained the time needed to study the various will immediately strive to find a new Fierce competition for beam time achievement in itself. Globally, only some “Coordinating a project like this is actually interim processes. equilibrium. This is common knowledge in The processes of interest occur at the four-five facilities at this level exist, and a task in its own right. Not only does the “Suppose you are looking at a lot of people chemistry, but by just which mechanisms femtosecond scale (a femtosecond is 10-15 competition for beam time is fierce. project involve a lot of people, but they also moving around in a busy central city area. “We are not yet at a stage where we can will the adjustment happen? An ambitious second). Also, they occur at the nano-scale, come from different disciplines and different Everybody is walking in different directions just study any molecule we would like to,” international project led by researchers meaning that many quantum mechanical Simulations and experiments scientific cultures. Sometimes, one has to but since there are people everywhere all Klaus B. Møller admits. “However, as we at DTU Chemistry and DTU Physics has phenomena are involved. In other words, interact devote more effort to securing that everybody the time, it is difficult to make observations will hopefully increase our skills in this opened the door to the study of processes measurements are extremely challenging. The newest facility is the European XFEL in is onboard and happy, than to doing science! about how people will move around in a discipline further, we expect to broaden happening internally in molecules. Hamburg, which opened in 2017, and where That is maybe not to everybody’s liking, but city. If you, however, remove all people in for the types of molecular systems we can “Ironically, the smaller an object you want to Klaus B. Møller and colleagues had beam personally I enjoy this side of the work. No instance one square, you can learn a lot from look at. Ground-state studies open a new As an example, internal molecular energy study, the larger an instrument will you be in time in May 2019. group in one country would be able to do this seeing how this void will be filled again. playing ground. After all, nearly all chemical distribution is of interest to solar cells. need of,” Klaus B. Møller smiles. kind of work alone.” Klaus B. Møller says. This is what we do in the experiment. We reactions happen when molecules are in Improving photovoltaic material efficiency “Each time, we need to do extensive see how the ground-state molecules react to their ground-state.” – measured by how large a proportion of the In this context, the large instrument is the computer simulations in order to establish New area: Looking at the disturbance – in other words, how the solar energy received will be converted into The Linac Coherent Light Source (LCLS) that what we have in mind is actually ground-state molecules system regains its equilibrium.” electric power – is an ongoing effort. And at Stanford University, USA. The core of possible. And later, as we get the beam Recently, a smaller strongly DTU-based this is far from the only possible application, LCLS is a kilometre-long X-ray free-electron time and experiments are initiated, we will research team – including also Associate Surprising role of the solvent Professor Klaus B. Møller notes Klaus B. Møller: laser (XFEL). The laser is able to generate do several simulations interacting with Professor Niels E. Henriksen from DTU The initial “freezing” of a sub-population [email protected]

8 9 ANNUAL REPORT 2019 ORGANIC AND INORGANIC CHEMISTRY A novel approach to treatment of Rheumatoid Arthritis

Sprung from DTU Chemistry, Rheumatoid Arthritis (RA) is an auto­immune do not have elevated levels of ACPA, and Associate Professor Kira Astakhova disease and chronic inflammatory disorder 15-20 % even have lower-than-normal levels, researches within synthetic biology – an interdisciplinary area between chemistry and start-up company IBIO TECH associated with progressive disability and i.e. they are sero-negative. ANC0031802 will biology that aims to design and redesign has patented a prodrug reduced life time expectancy. Affecting only help sero-positive patients. of biological components and systems. which could become the first around 1 % of the world’s population, RA has large socio-economic costs. “Around 60 % of RA patients will benefit product that not just dampen from the treatment. Still, these are both the Rheumatoid Arthritis symptoms, RA is characterized by synovial inflamma- most severely affected by the disease and the tion and tissue damage. The origin and hardest to treat,” Kira Astakhova comments. However, even in a worst-case scenario “This is an astonishingly high number,” Kira less drastic ways than by inhibiting TNF,” but actually cures patients. cause are unknown, and no cure currently where IBIO TECH would have to abandon Astakhova comments. “This underlines the explains Kira Astakhova. exists. However, treatments that reduce the ANC0031802, it would not have to be the relevance of founding a company with RA as symptoms and the activity of the disease First clinical trials in 1.5 years end of the story: its focus here. We do not need to look far to “Early diagnosis will benefit all RA patients, have emerged over the last three decades. For patients in acute need of a RA cure get the clinical samples we want. And again, including the ones that we hope will be able The standard of care treatment is by today, the young company is unfortunately “Our real invention is actually not the it seems that genetic factors are a part of the to benefit from treatment with our drug disease-modifying anti-rheumatic drugs not able to assist. For obvious reasons, product itself, but a technology platform explanation.” candidate.” (DMARDs), where methotrexate (MTX) is pharmaceutical development is subject to capable of delivering several similar the frontline drug. strict regulation and high safety standards. products. So, should ANC0031802 fail for A better understanding of the genetics Therefore, it takes a long time from a drug some unforeseen reason, we will able to come involved should also help the diagnostic Associate Professor Kira Astakhova Now, Danish start-up company IBIO TECH candidate is discovered until it can enter the up with alternative candidates very quickly. abilities, Kira Astakhova hopes: [email protected] has patented a prodrug based upon an market. About ten years is the normal time In fact, we are already working on some “It is a major problem, that patients are often entirely new concept. frame. IBIO TECH has completed the first other prodrugs as backups. But obviously, diagnosed at a very late stage where the two years of this journey. we would have to reconsider our milestones, prognosis is much worse than if treatment IBIO TECH “Our drug candidate is designed to reach the and patients would have to wait longer before was commenced earlier on.” synovial fluid and bind key antibodies at the About 18 months from now, ANC0031802 they can be offered the treatment.” Founded in 2018, IBIO TECH today has a site of inflammation. This will provide both should become ready for phase 1 of clinical Why late treatment is risky staff of five: CEO and Business Developer a more effective treatment and a much lower trials. If the clinical results are satisfactory, Endemic to Scandinavia After RA onset, the level of ACPA is typically Daniel Zalomajev, CTO Sangita Khatri, level of side-effects compared to other drugs the product will proceed to phases 2 and While ANC0031802 can only benefit the very high and increasing rapidly. Here, it Clinical Developer Tue Wenzel Kragstrup, that are not equally specific,” explains IBIO 3, involving a large number of patients in 60 % sero-positive RA patients, the patients is absolutely necessary to reduce the level Founder Kira Astakhova, Associate TECH founder Kira Astakhova, Associate several countries, before, eventually, the final with normal ACPA levels and the sero- of ACPA, as otherwise the patient will be Professor at DTU Chemistry, and Co-Founder Professor at DTU Chemistry. drug approval can be applied for. negative patients are far from forgotten, severely handicapped and may possibly die. Professor Mads H. Clausen, DTU Chemistry. Kira Astakhova emphasizes: In effect, the only method to achieve this Positive effect in the most Somewhere along that timeline, costs will reduction within an acceptable timeframe The company is based on ongoing severe cases rise to levels beyond the capacity of any “Our goal is not just to develop medicine. is by inhibiting the signalling protein TNF fundamental research by Kira Astakhova The targeted antibodies are ACPA (anti-cyclic start-up company. We also strive to understand the underlying (tumour necrosis factor). Inhibiting TNF has in the field of nucleic acid and peptide citrullinated peptide antibody). A large group mechanisms. From a scientific point of a significant downside, since – as suggested aptamers. Her interests include ultra- of RA patients has elevated levels of ACPA – “At that point we will have to exit the view, it is really interesting how the disease by the term tumour necrosis - the protein specific nucleic acid binding and nucleic they are said to be sero-positive. ACPA is both development, meaning we will sell or license manifests itself so differently in different plays a key role in the body’s anti-cancer acid/peptide/anti-body interactions. The indicative of the RA diagnosis and a target the product to an existing pharmaceutical people. We know that a large genetic defence by identifying cancer cells and research is supported by development for medicinal treatment. As the IBIO TECH company with the economic capacity component exists. If we can disclose the trigger their death. of thermodynamic and optical detection prodrug – for the time being still referred to necessary to take the product through the more specific genes involved, we will be able techniques with applications in strategies under its “lab name” ANC0031802 – binds to final stages and into marketing,” says Kira to be even more specific as to which patients “So, while most patients with RA in an for nucleic acid and peptide synthesis. ACPA, the level of the antibodies decreases, Astakhova, estimating this exit to take place will benefit from which drugs.” advanced stage will have their symptoms leading to milder symptoms and eventually about six years from now: reduced through TNF inhibition, this Kira Astakhova has received several stopping progress of the disease. Another mystery is how RA is endemic to comes at the price of an increased risk of prestigious grants including the Sapere “That is, if we do not encounter any Scandinavia. While 8 % of the Scandinavian cancer. Therefore, it is highly desirable that Aude Elite scholarship, the NIH (National It should be noted, that the prodrug is not unpleasant surprises like unforeseen population is at risk of developing RA, the RA is diagnosed in the early stages where Institutes of Health, USA) grant, and Villum universal for RA patients. Some patients side-effects.” number is less than 1 % on a global scale. it is still possible to control ACPA levels in Young Investigator Grant.

10 11 ANNUAL REPORT 2019 ORGANIC AND INORGANIC CHEMISTRY

defined as “a substance composed of two The ceramic monolith is manufactured by The MACBETH project began November distinct ions that is liquid below 100°C”. LiqTech in Ballerup, which specializes in 2019 and will run for 4.5 years. silicon carbide materials for applications In other words, an ionic liquid has a very mainly in the water sector. Evonik The new process is optimized for production high boiling point. This is essential because Performance Materials will head the of pentanal from C4 raffinates with butenes, Smart chemistry the amounts lost due to vaporization are overall implementation of the technology. but is viable for gas phase production of close to zero when operated in a continuous other aldehydes from other types of alkenes. gas phase system even under elevated High level of technical readiness temperature. The ionic liquid is integrated The partners have developed the new “We have demonstrated the system to into a so-called SILP – Supported Ionic process in a joint project with EU financing, be especially effective for production of Liquid Phase – catalyst. SILP systems are ROMEO. Following the successful initial pentanal from butenes. Satisfyingly, we are to save vast a long-standing research area at DTU development, the partners have been granted able to obtain very close to 100 % selectivity Chemistry. The concept allows for high a further project, MACBETH. to pentanal and operate for several thousand efficiency due to a highly exposed surface of hours without catalyst deactivation.” the ionic liquid phase resulting in excellent “The fundamental technology has been diffusion dynamics. Further, the SILPs can proven, and we are now ready to move Pentanal is mainly used as the starting point be designed as highly selective for the given from research and closer to industrial for production of plasticizers, flavourings, in purpose – in this case immobilization of the implementation. To use the EU terminology, resin chemistry, and for rubber accelerators. amounts of CO2 rhodium-based catalytic complex. the MACBETH project will take the technology to technical readiness “The overall solution allows for continuous level 7, meaning demonstration in an Professor Anders Riisager operation of the catalyst in the reactor with industrial operational environment,” Professor [email protected] Riisager simultaneous removal of products. Any says Anders Riisager. [email protected] Aldehydes are manufactured with traditional production. The key idea flow of liquid or gas phase feedstock through potential problem with loss of catalyst or in large quantities by chemical is to integrate two processes – reaction a solid, porous catalyst (this is the usual form deactivation of the catalyst is prevented, and separation - which are normally of heterogeneous catalysis), the catalyst and and importantly we are able to perform the companies all over the globe. performed as consecutive steps into just the feedstock are dissolved in a liquid solvent process with just 20 % of the energy use in A new process co-developed one step in a combined reactor system, and the catalyst only recaptured later. the industry today,” says Anders Riisager. thereby minimizing energy use for the total at DTU Chemistry will reduce production,” says Professor Anders Riisager, “Homogeneous catalysis is generally avoided carbon emissions from aldehyde DTU Chemistry. for large-scale industrial applications due to the need for recapture of the catalyst. production by as much as 80 %. Combing two processes in one However, in this case homogeneous catalysis Alkenes are converted into aldehydes by a is necessary in order to obtain the desired reaction type known as hydroformylation. selectivity towards the linear aldehyde Detergents, fragrances and flavourings Here, a formyl group (CHO) and a hydrogen molecules and because the aldehydes have an are examples of products made in large atom are added to the carbon-carbon double unfortunate tendency to react mutually into quantities with aldehydes as starting point. bond in the alkene forming either a linear larger molecules. If a heterogeneous catalyst Given the scale of aldehyde production, a or a branched aldehyde. Various versions of was used, these molecules would accumulate new energy efficient process co-developed by the process exist, but they all involve high in the solid, porous matrix gradually researchers at the Centre for Catalysis and pressure of syngas, CO and H2 (in the 10-100 deactivating the catalyst. By adding the Sustainable Chemistry at DTU Chemistry is bar range), elevated temperature (80-200 °C) catalyst directly into the feedstock solution about to make a significant contribution to and the presence of a transition metal this problem is avoided,” explains Anders climate change mitigation. catalyst. Usually the process is designed to Riisager, noting that hydroformylation of produce mainly the linear aldehyde. alkenes is the largest existing application of More than 10 million tons of aldehydes homogeneous catalysis. are manufactured each year. Aldehydes Hydroformylation of alkenes has been are produced from alkenes which are around since 1938, and regardless of Avoiding vaporization unsaturated hydrocarbons that contain the variety of specific setups, the basic The new process is developed by Danish carbon-carbon double bonds. Normally chemistry has remained the same – and company LiqTech International, German the alkenes are obtained as by-products will continue to be so, also when the new company Evonik Performance Materials from fossil feedstock in the petrochemical process become implemented. The main together with academic groups from CSIC industry. However, they may also be change in comparison to the traditional Madrid, RWTH Aachen, University of produced from renewable feedstock like use of hydroformylation is the new focus Erlangen-Nuremberg and DTU Chemistry. biomass. on creating more energy efficient processes A rhodium-based catalytic complex – both in order to save energy costs and catalyses the hydroformylation. While “While research many places – also at DTU contribute to climate change mitigation. this in itself is not extraordinary, the real Chemistry – strive to produce alkenes from development is the integration of the Schematic drawing and biomass, this is not the focus of the present Unlike most other chemical industry catalysis and the product separation in photograph of the cylindrical project. What we have developed is a new processes that produce bulk chemicals in one process using an ionic liquid system porous monolith consisting of a SiC core, SiC skin, and silica wash- technology able to convert alkenes into huge quantities, the hydroformylation of immobilized in a porous ceramic monolith coat. Detailed schematic drawing aldehydes in a far more energy efficient and alkenes is carried out by homogeneous with an outer polymeric membrane of the pore structure before and environmentally benign way compared catalysis. Instead of directing a continuous installed in the reactor. An ionic liquid is after liquid impregnation.

12 13 ANNUAL REPORT 2019 PHYSICAL AND BIOPHYSICAL CHEMISTRY Shedding Light on Molecular Recognition Mechanisms

New experimental approaches non-covalent intermolecular forces stabilizing “There is a fundamental need for Other Research Activities are unveiling the weak non- weakly bound molecular complexes normally experimental approaches which are able are 10-100 times weaker than covalent to investigate the intermolecular energy The THz cluster spectroscopy group of Associate Professor René Wugt Larsen covalent forces between bonds (~5-50 kJ∙mol-1), the inter-molecular balances associated with the interplay of has recently established fruitful internal collaborations with the DTU Chemistry molecules that historically vibrational modes introduced by the weak non-covalent forces such as directional molecular material research groups of Associate Professor Kasper S. Pedersen complexation between molecules are detected intermolecular hydrogen bonds and and Associate Professor Martin Nielsen concerned with the spectroscopic have been challenging in the less accessible terahertz (THz) spectral dipole-dipole interactions, non-directional characterization of novel metal-organic frameworks and organometallic complexes. to study in the arduous region”, says Associate Professor René Wugt long-range van der Waals forces and steric In addition, a close external collaboration with the Danish Hydrocarbon Research & Larsen, who is in charge of the THz cluster repulsion between molecules”, says René Technology Centre (DHRTC) has recently been established related to spectro­scopic terahertz spectral region. spectroscopy group at DTU Chemistry. Wugt Larsen. investigations of fluid-fluid and surface-fluid association mechanisms.

The accurate interaction strength, Soft “Quantum Crystals” Molecular recognition, the mechanisms by directionality and cooperativity of the weak The demand for THz spectral signatures which biological macromolecules interact "contacts" associated with non-covalent of weakly bound molecular van der Waals either with each other or with other various intermolecular forces can be probed directly complexes has urged for the development of field-free host medium, where the large- in the soft para-H2 medium and would small substrates with high specificity via these large-amplitude modes arising complementary experimental approaches amplitude zero-point lattice motion offers never form under ambient conditions”, and affinity to form specific molecular from the now hindered rotational and employing conventional radiation sources, significantly free space for embedded guest says Associate Professor René Wugt complexes, constitutes the foundation for translational motion of the subunits relative where the experimental sensitivity is molecules and the crystal behaves as an Larsen. “The observed THz signatures all processes in living organisms. Proteins, to each other. These resulting THz spectral governed by significant number densities “extremely cold gas”. and intermolecular force fields provide the most important class of biological signatures are thus crucial in order to of transient molecular systems trapped in challenging experimental benchmarks macromolecules, all realize their vital characterize with unprecedented accuracy ultra-cold inert environments. In newly developed experimental setups even for the most sophisticated quantum The new THz cluster spectroscopy experiment for biological specific functions through the the intermolecular potential energy surface the research group of Associate Professor chemical methodologies”, he continues. investigations of weakly bound molecular van der Waals complexes doped in para-H2 “quantum association to other molecules. spanned by the subunits and yield rigorous The research group of Associate René Wugt Larsen has been able to crystals” at 4 K. experimental benchmarks to validate or Professor René Wugt Larsen has recently characterize in great detail the large- The PhD Students Dmytro Mihrin and Knowledge of the detailed mechanisms improve quantum chemical methodologies. demonstrated that highly enriched para-H2 amplitude vibrational motion of weakly Alexandre Voute have developed a fully- responsible for molecular recognition “quantum crystals” of >99,95 % purity bound molecular van der Waals complexes automated cryogen-free para-H2 synthesis phenomena and an accurate quantification However, the relevant part of the spectrum offers multiple advantages as a host for embedded in enriched para-H2 at 4 K. apparatus based on a temperature of the energetics, which drive the association is denoted the “THz gap” as historically it low-temperature THz cluster spectroscopy controlled closed-cycle helium cryo-cooler processes, will therefore help to facilitate has been challenging to produce intense arising from the unique “quantum nature". Proof-of-Concept at DTU Chemistry for these studies and the workshop at DTU the discovery, design, and development of radiation with these wavelengths. The only The project was initiated in 2013, when Chemistry has constructed many vital new drugs. high-brightness sources of broadband The H2 molecule exists as two spin isomers: René Wugt Larsen obtained a 5-year parts for these new experimental facilities. THz radiation are offered by large-scale para-H2 with paired nuclear spins or Sapere Aude Research Leader grant “Theintra -molecular vibrational ‘fingerprints’ synchrotron radiation facilities as Canadian ortho-H2 with unpaired nuclear spins, where from the Independent Research Fund A future aim is to address one of the of stable molecules, kept together by covalent Light Source, Synchrotron SOLEIL (Paris), the latter has a ”reactive” magnetic moment. Denmark / Natural Sciences (FNU). Later, most fascinating phenomena in nature chemical bonds, are usually detected in the Australian Synchrotron and recently at the In the ground state of this soft material, the Danish Hydrocarbon Research and referred to as the “homochirality of infrared (IR) spectral region. However, as the free-electron laser facility FELIX (Nijmegen). the para-H2 molecules provide an almost Technology Centre (DHRTC) has provided life“. The chemistry of life is built almost further funding. The “proof-of-concept” exclusively on left-handed amino acids and The electromagnetic spectrum and the variety of has recently been published in the journal right-handed sugar molecules. Often one spectroscopies (MW, THz, IR and UV) associated with the different quantum states of molecular Physical Chemistry Chemical Physics. chiral form of a drug is active, while the systems [adapted from Anal. Bioanal. Chem. 2010, The large-amplitude other(s) are either inactive or have severe 397, 1009-1017]. hindered internal “In this work, we have revealed interesting adverse effects. It has been argued, that a rotational motion for molecular recognition processes and we true breakthrough in our understanding a kinetically formed have managed to trap a variety of exotic of these molecular chirality recognition "exotic" conformation molecular systems. These molecular phenomena can be achieved by accurate of the ternary CS2- (H2O)2 van der Waals systems are formed due to the kinetics THz spectroscopic investigations of chiral Associate Professor René Wugt Larsen complex in para-H2. associated with the mobility of molecules drug-receptor model systems. [email protected]

14 15 ANNUAL REPORT 2019 PHD DEFENCES

Atomistic Mechanisms of Functional Molecules

The global demand for energy is rising and for a long to an exponential growth of computational time with time solar energy has been considered as one of the best the increase of nuclear degrees of freedom. On the other renewable and clean alternatives to unsustainable energy hand, it has been evidenced that the solvent can alter the sources. One of the big challenges in using solar energy dynamics of the solute molecule significantly. is to make its conversion and storage cheap, which is of The thesis provides a reliable scheme for describing particular importance in large-scale production of solar solvent structural dynamics using MD simulations and cells. This requires finding low-cost, earth-abundant, shows that implicit the polarizable continuum model PhD from Mostafa Abedi and environmentally friendly materials. In this regard, (PCM) can provide a trade-off between accuracy and PhD theoretical chemistry methods by providing a deeper computational cost for accounting for the solvent effects Funded by knowledge and understanding play an important role as on the solute intramolecular relaxation processes. 2/3 Independent a complementary tool alongside experimental techniques This opens for the possibility of using these solvation Research Fund and in development of new and high efficient materials. approaches in quantum dynamics simulations of Denmark, 1/3 DTU Chemistry This PhD thesis targets theoretical investigations on photorelaxation processes. DTU Chemistry transition metal complexes and photoswitchable organic Supervisors molecules, two classes of materials relevant for solar Klaus B. Møller [email protected] energy conversion and storage, using a wide range of DTU Chemistry takes pride in educating PhDs at the Power Performance theoretical approaches. The main results of this project Niels Engholm Henriksen highest international level. We present a diverse Excellent scientists must also be able to communicate are atomistic insights into the mechanisms behind a [email protected] research education in modern chemistry, which their research results efficiently. Therefore, DTU variety of light energy conversion processes. contributes to the development of cutting edge science Chemistry offers each PhD student an intensive A deep understanding of the photorelaxation Mátyás Imre Pápai [email protected] at the department. The goal for all PhD students is to communication course (1.5 ECTS) to practice their processes occurring upon light absorption would be publish in leading journals and participate in leading presentation techniques to perfection. A cornerstone necessary for designing and developing more efficient international conferences during their three year long in this regard is the annual PhD Symposium at which materials. Quantum description of the photorelaxation The molecular structures of Fe(II) polypyridine deriv-atives research education. stakeholders from the industry are invited to attend dynamics in the presence of solvent is not feasible due and their MLCT lifetimes in H2O and CH3CN solutions. both oral presentations and a poster session by the PhD ChemClub Department’s PhD students. The PhD students at DTU Chemistry are strengthening their professional and social network at the Depart­- Contact us! ment. They do this through the PhD ChemClub. In the following pages, you can get acquainted with PhD students run the ChemClub, and they arrange the DTU Chemistry PhD Defences of 2019. All Protein structure and protein-protein several annual events: PhD Symposium, post-graduate supervisors invite you to get in touch, if you are career events with experts from industry and academia, interested in the full thesis, in further information, interactions in formulation inspiring talks by invited speakers, and social or in a possible collaboration. You are also welcome to gatherings. We invite interested candidates to have a contact the Head of the PhD School, Professor Erling look at our website kemi.dtu.dk/English, where you can H. Stenby, Head of Department, [email protected] read more about our PhD programme as well as the The use of biopharmaceuticals in the treatment of and albumin-degludec mixtures were proposed. The DTU Chemistry research areas. diseases such as diabetes, cancer, and hemophilia has albumin-detemir hexamer solution structure shows four increased dramatically over the past decades. Despite possible detemir binding sites. These binding sites were The 2019 edition of the PhD Symposium - held at Konventum, Elsinore - was filled with interesting presentations and posters. Several industry partners showed up their many advantages such as high potency, specificity, investigated by MD simulations and molecular mechanics and got a first hand impression of the PhD school at DTU Chemistry. They were and low toxicity, many biopharmaceuticals suffer Poisson-Boltzmann surface area free energy calculations. impressed by the overall level of research and presentation techniques. from inherent chemical and physical instabilities and The overlapping FA3-FA4 binding site on albumin was short plasma half-lives, which make their formulation found to be the most favorable detemir binding site. Line Ryberg development and delivery challenging. The presence of albumin was found to enhance Abildgaard PhD Lipidation is a successful strategy for extending the detemir’s stability against freeze-thaw and agitation half-lives of peptide drugs through lipidation-induced stresses almost independently on complex formation, Funded by self-association and association to albumin. Though suggesting that albumin-detemir complex formation DTU Chemistry albumin-association is exploited by several approved does not lead to further stabilization. Supervisors lipidated peptide drugs, structural knowledge about Günther H.J. Peters the albumin-peptide complexes and their interactions [email protected] on the atomic level is limited. This thesis treat self- Pernille Harris association and albumin-association of two lipidated ph@kemi.dtu.dk insulin analogues, insulin detemir and insulin degludec, Jens T. Bukrinski through an interdisciplinary approach using small angle X-ray scattering (SAXS) and molecular dynamics (MD) simulations. The first solution structures of a detemir trihexamer, and albumin–insulin analogue complexes in 1:6, Schematic representations of 1:12, and 2:12 stoichiometries based on SAXS data the sequences of native insulin, were modeled, and equilibria for albumin-detemir deglutec and detemir.

16 17 ANNUAL REPORT 2019 PHD DEFENCES

Development of detection-receptors Cobalt-Catalyzed Dehydrogenation for sialic acids of Alcohols and Amines

Sialic acids are a diverse family of carbohydrates reversible disulfide bonds to connect building blocks Usually, reactions with hydrogen gas are catalyzed by liberation of hydrogen gas and water. The mechanism widely distributed in human tissues and specifically under thermodynamic control. When the target is the platinum metal group, and there is therefore a great has been investigated with a number of labeled substrates present in both N- and O-linked glycans, where they added, the distribution of the species in the library interest in finding cheaper alternatives. Cobalt is one of and the catalytically active compound is believed to be a constitute the terminal residue of the oligosaccharides changes leading to an amplification of effective receptors. the commonly available transition metals, and cobalt cobalt (I) complex with the particular phosphine ligand. on glycoproteins. Sialylation is important to a protein´s The amplified receptors were isolated and the binding compounds also possess interesting properties that are This complex reacts with the alcohol and cleaves off two function and its physical and pharmacokinetic studied both qualitatively and quantitatively using relevant in catalytic reactions. hydrogen atoms in the same step, releasing the aldehyde properties, and the ability to monitor the degree of 1H-NMR spectroscopy and a UV spectroscopy indicator Vanessa Baj The thesis describes two projects, both of which deal and subsequently forming the imine. Hydrogen gas is Fabrizio Bottaro sialylation is important in the development of protein- displacement assay. PhD with hydrogen gas evolution with in situ cobalt catalysts. then liberated from the catalyst and the catalytically PhD

based drugs. The second approach was combinatorial chemistry. Funded by In the first project, a homogeneous cobalt catalyst has active compound is restored. Funded by Novo Nordisk produces a drug based on a Synthetic methodology was developed for the high- Marie Curie, EU been formed in situ from cobalt (II) bromide, zinc In the second project, dicobalt octacarbonyl has been Villum Fonden glycoprotein called Recombinant Activated Factor VII throughput solid phase synthesis of cyclic peptides. metal, and a special phosphine ligand. The compound heated, thereby decomposing into cobalt nanoparticles. Supervisors Supervisors (rFVIIa), better known as Novo-Seven®, taken by patients Three cyclic peptides libraries were synthesized. Among Sophie Beeren thus formed catalyzes the coupling between alcohols These particles catalyze the coupling between two Robert Madsen with haemophilia or other coagulation deficiencies. the three different high-throughput methods of analysis [email protected] and amines to form the corresponding imines by the amines by releasing hydrogen gas and ammonia, thereby [email protected] In adults, the pharmacokinetics of rFVIIa is directly that were tested, a competitive direct ELISA assay was again forming imines as the product. The coupling can Carsten Behrens Mads Hartvig Clausen dependent on the number of attached sialic acids. rFVIIa selected as the most take place both between two different amines and as [email protected] is isolated as a mixture of compounds with different suitable and reliable. Thomas E. Nielsen a self-coupling of a single amine. The nanoparticles degrees of sialylation and no further purification is The three libraries have been characterized microscopically and they were Multiple reactions performed. The aim of this project was the development were analyzed submitted to the same found to have a narrow distribution with an average of small organic molecules able to selectively recognize and four potential temperature were run diameter of 2 nm. The heterogeneous cobalt catalyst sialic acid and suitable to be incorporated into a receptors were found. on Radleys carousel can be isolated from the amine coupling and reused in chromatographic purification system. connected to the Schlenk a new reaction. In summary, in this project an in situ- Mechanism of action of ASPG receptor. Asialoglyco- line, in order to perform The first methodology explored was dynamic protein receptors in the liver are able to recognize only efficiently the largest formed cobalt catalyst was developed from the cobalt combinatorial chemistry. Dynamic combinatorial non sialylated serum protein. Thus, sialylated protein number of tests under carbonyl complex and trioctylphosphine oxide, for the libraries of potential receptors were generated using are protected from uptake and degradation. the same conditions. acceptorless dehydrogenation of amines into imines.

Chemical reactions and intermediates Development of detection-receptors followed by DNP NMR for sialic acids

Modern analytical chemistry has sought to develop NMR, increasing the otherwise low sensitivity of the Wearable biomedical electronic devices (WBEDs) can Then these carbon-based paper-like films are either “in-situ” methods of analysis. These methods examine method ten-thousand fold. be attached to human epidermal tissues and used for directly used as high-performance FSSSC electrodes, the system while the reaction is happening, allowing the NMR is one of the most common methods for analyzing diverse health-related chemical/biological or employed as advanced flexible substrates to load characterizing of catalysts in their working state, and the discovering the structure of organic molecules. By signals. Wearable sensors and power devices, which different electrode active materials and realize superior observation of chemical transformations in real time. enhancing the method using dDNP, we facilitate a are mainly constituted by flexible composite electrodes bifunctional features. Based on a series of structural This thesis has developed the application of number of otherwise unfeasible in-situ investigations. (FCEs), are generally regarded as two functional core and compositional optimization, the carbon-based dis­solution dynamic nuclear polarization (dDNP) Prior work using dDNP has primarily investigated Peter Andreas Boeg components of WBEDs. Therefore, developing advanced FCEs developed in this Ph.D. study possess excellent Xianyi Cao nuclear magnetic resonance (NMR) spectroscopy. This metabolic and medical systems. In this thesis, we seek PhD FCEs capable of realizing high-performance physiological comprehensive performances towards energy storage or/ PhD technique adds an extra, preliminary step to conventional to expand the scope of the method by demonstrating its Funded by index monitoring, energy storage or even both of them has and biosensing. Moreover, compared with other types Funded by applicability to catalytic systems. The systems investigated 2/3 Danish National attracted considerable research attention. of FCEs, the carbon-based FCEs developed in this Ph.D. China Scholarship were the formation of solketal, a green additive to diesel; Research Foundation, In recent years, due to their multiple function and study exhibit prominent practical advantages, such as Council 1/3 DTU Chemistry the hydrogenation of olefins, a commonly used chemical performance superiorities, carbon-based paper-like films low cost and facile fabrication. Supervisors reaction; and the 2nd generation Hoveyda-Grubbs Supervisors have been preliminarily exploited as advanced substrates Jens Øllgaard Duus catalyst, used for metathesis reactions. Susanne Mossin of FCEs. [email protected] [email protected] The application of the method to catalytic systems was This Ph.D. project is devoted to the design, Qijin Chi successful, providing a number of interesting results. It Jens Øllgaard Duus fabrication, characterization and application of novel [email protected] was demonstrated how we could follow the reactions of carbon-based FCEs. Employing a series of facile, catalytic systems in real-time, observing the consumption Jan Henrik efficient, and scalable fabrication techniques, the of substrates and formation of reaction intermediates and Ardenkjær-Larsen engineering of three types of carbon-based paper-like [email protected] products. Changing the conditions during the reaction, films are explored. The films include nitrogen-doped by reducing the hydrogen flow, had a direct, observable Magnus Karlsson hybrid dimensional nanocarbon based paper electrodes, [email protected] gold nanoparticles decorated reduced graphene oxide impact. The method was also utilized for analyzing the Schematic illustration of structure of a catalyst, and the changes incurred to the papers, and copper cobaltate nanowires loaded on the N-RGO-CNT-CBNP-P Activation study of [Rh(NBD)(DPPB)]ClO4: nBA structure as the catalyst was activated or inhibited. activated graphite papers. structure.

18 19 ANNUAL REPORT 2019 PHD DEFENCES

NMR Spectroscopic Exploration of Designing zeolite-based catalysts for production Tin-Catalysed Biomass Conversion of fuels and chemicals

In the pursuit to replace fossil resources with more methyl lactate. This influence was investigated further, The world is struggling with different challenges methanol-to-hydrocarbons, and dehydro­aromatization sustain­able alternatives, the chemocatalytic conversion leading to three findings: 1; the effect was proportional such as depletion of fossil fuels, growing gap between of ethane. In particular, MFI structured zeolites of carbohydrates provides an important method for to the ratio of alkali salt and tin atoms in the catalyst, 2; energy demand and production, and most importantly with 3-dimensional channels including ZSM-5 and pro­ducing new functional chemicals. This PhD project the reaction selectivity is under kinetic control, and 3; emergent environmental issues. Therefore, alternative silicalite-1 were employed in the presented works. focuses on the use of a Sn-Beta zeolite catalyst for the alkali salts facilitate breaking of carbon-carbon bonds. environmentally friendly resources for production of Different morphologies of MFI zeolites were synthesized, con­version of glucose, xylose and glycolaldehyde in The reaction mechanistic pathways were investigated chemicals and energy are necessities. However, the characterized and applied in catalyst design. More methanol, to form α-hydroxy esters, such as methyl using carbohydrates with isotope-labeled hydrogen Samuel G. Elliot transition and utilization of new resources requires specifically, zeolites were used as catalyst support for Farnoosh Goodarzi lactate and methyl vinyl glycolate (MVG), with interesting and carbon atoms. The key findings from this were that PhD development of novel technologies. metals and/or as solid acid catalysts in solid phase for PhD

potential as building blocks for polymer production. isomerization competes with dehydration to determine Funded by Thus, the aim of this thesis was to develop new aforementioned chosen reactions. Funded by The project is concerned with the development and use the selectivity for DPM / THM. In addition, it indicates Innovation Fund efficient catalysts and investigate their performances The deactivation challenge in each process and Haldor Topsøe A/S of NMR spectroscopic methods to identify and quantify that all carbohydrates remain connected to the tin in the Denmark in different energy and chemical production processes catalyst was different. Thus, the cause of deactivation was Supervisors several new products in the catalytic reaction without catalyst until fully reacted. Supervisors such as CO2 attempted to be considered in designing a more active, Søren Kegnæs having to purify samples or isolate new substances. Overall, this project has contributed many additional Robert Madsen hydrogenation selective and deactivation-resistant catalyst. This was [email protected] Among other things, two new interesting molecules were details about the Sn-Beta catalyzed conversion of carbo­ [email protected] to methane, achieved by for instance addition of second mesoporosity Poul Erik Højlund identified from the carbohydrate conversion, namely hydrates through the study of intermediates, product Sebastian Meier (hierarchical zeolite), zeolite surface modification, metal Nielsen methyl 2,5-dihydroxy-3-pentenoate (DPM) and methyl distributions and the tracking of atoms during the [email protected] encapsulation and metal stabilization using sulfur. As 2,4,5-trihydroxy-3-pentanoate (THM). The yields were reactions. Bi-functional a result, catalytic performance including selectivity Peter Fristrup zeolite- optimized by varying several reaction conditions, yielding encapsulated towards desired products, conversion and life-time were 19.4 % of THM and 42 % of DPM. It was subsequently metal nano-­ improved for the developed catalysts. shown that DPM could be used to prepare polymers. particle catalyst In summary, this thesis offers promising solutions Alkali salts such as potassium are known to modify 1H-13C spectral region of secondary alcohol to convert ethane for catalyst deactivation by designing novel catalysts for CH-groups (indicated by small spheres) to aromatics the reaction selectivity of the Sn-Beta catalyzed three important processes that potentially provide more adjacent to carboxylic groups, showing the such as benzene carbohydrate conversion so that the transformation signals of both known and new α-hydroxy Toluene and environmentally friendly approach for production of follows a different reaction pathway and primarily yields esters formed from conversion of glucose. xylenes in one step. fuels and energy.

Solution structure of glucagon-like peptide-1 analogues and their Characterization of Protein-Excipient Interactions and Protein-Protein interactions with the endogenous receptor and albumin Interactions on the Molecular Level Using In-Silico Simulation

Since the beginning of the 20th century, the interest linker in between the long FA chains and GLP-1, only Protein and peptide therapeutics (PPTs), also called supplemented with NMR chemical shift assays were used for glucagon-like peptide-1 (GLP-1) has been growing. partial HSA interaction is observed. This concludes that biologics, are often characterized by high specificity and to determine the order of cystines reduction. Firstly, due to GLP-1’s ability to regulate insulin secretion, longer FA chains should increase the half-life. But what potency with low toxicity and has therefore interested Peptide-excipient interaction hotspots were deduced and recently, due to its promising properties in treating about the biological effect? This was investigated using many pharmaceutical industries wanting to develop from MD simulations in combination with MST obesity, preventing cardiovascular diseases, and possibly computer simulations, and the results indicate that the medicines to treat severe human diseases. and NMR measurements. In the classes of proteins, even dementia. However, it quickly became clear that effect depends on the site of FA attachment. Furthermore, As a part of the consortium Protein-excipient Inter­ conformational stability of human serum transferrin (Tf) GLP-1 cannot be administered as a drug, since its half- longer FA chains seemed to be more effective, which Tine Maja Frimann actions and Protein-Protein Interactions in formulation and conjugate fusion protein human serum albumin– Sowmya Indrakumar life in the body is very short. In fact, it is cleared already goes well with the half-life extension possibly being more PhD (PIPPI) this PhD thesis describes fundamental research neprilysin (HSA-NEP) were examined by combining PhD within a few minutes, preventing its usage as a drug pronounced for longer FA chains. Funded by carried out to investigate the effect of pH and varying small angle X-ray scattering (SAXS) and MD simulations Funded by without remedying modifications. Several strategies have In addition, the pewrformed investigations, using a DTU Chemistry concentrations of different additives on diverse classes in various formulation conditions. Marie Curie, EU, PIPPI been developed to successfully prolong the half-life of combination of experimental studies and computer simu- of PPTs. In the class of peptides, the wild-type plectasin The research findings presented in this thesis indicate Supervisors Supervisors GLP-1. One solution consists of attaching a fatty acid (FA) lations, could provide Günther H.J. Peters – known as cysteine stabilized antimicrobial defensing the usefulness of combining in-silico and experimental Günther H.J. Peters chain to GLP-1. This is believed to cause interactions with intel on a level that [email protected] – and three variants were investigated using molecular techniques [email protected] human serum albumin (HSA), a carrier protein in the is very difficult to dynamics (MD) simulations in combination with and that this Pernille Harris Werner Streicher blood, as well as oligomerisation. However, it is vital that obtain using only [email protected] microscale thermophoresis (MST) and nuclear magnetic approach the biological function of GLP-1 is maintained. one of the methods. resonance (NMR). can aid in Pernille Harris Jens T. Bukrinski [email protected] In this study, the half-life extending properties of Therefore, the results All the plectasin variants were conformationally designing different attached FAs were investigated experimentally. of this study also stable during the course of 100 ns MD simulations at all new The results show that longer FA chains lead to larger present themselves pH and salt conditions. However, flexibility in the loop strategies oligomers, and that the addition of a charged linker as a methodology for containing a distinct anionic tetrapeptide stretch close to for the between GLP-1 and the FA chain leads to more stable, facilitating atomic the N-terminus increases with pH due to the change in formu­lation Electrostatic potential Interaction strength surfaces calculated for but smaller oligomers. In relation to HSA interactions, level investigations electrostatics. The conformational stability of the plectasin of biologics. between peptide and A. PO, pH 5; B. HO, pH it was shown that attaching medium to long FA chains of peptide drugs. receptor extracellular variants are attributed to the presence of three cystines. 5; C. PO, pH 6.5; D. HO, cause full interaction with HSA, whereas if there is a domain. Therefore, thermodynamic integration MD simulations pH 6.5.

20 21 ANNUAL REPORT 2019 PHD DEFENCES

New polymer building blocks from Enzymatic Biofuel Cells and Biosupercapacitors: The body itself bio-based methyl vinyl glycolate can drive power supply for miniaturized medical equipment

Methyl vinyl glycolate (MVG) is a chemical compound are still produced from oil-based products. The thesis Miniaturized implantable and self-sustained power biofuel cells and biosupercapacitors that can produce that can be produced in bulk through a catalytic describes the transformation of MVG into a number of supplies for personalized medical devices – based on electrical power directly from fuels in biological fluids, process from carbohydrates. MVG (also called methyl new compounds that have potential as building blocks energy conversion or energy storage – hold significant or store charge using biodegradable catalysts (e.g. 2-hydroxybut-3-enoate) is thus a new substance in the for the production of polymers. promise for monitoring and controlling human health enzymes), have therefore attracted great interest. series of bio-derived and renewable compounds that can The reactions involve the alkene and the alcohol and well-being. Biological power sources, such as The aim of this Ph.D. project is to fabricate novel help to reduce the dependence on chemicals from the in MVG, both of which are reactive functional groups type biological power sources using enzymes or petrochemical industry and thereby contribute to the for different transformations. The alkene has been Bo Michael Jessen proteins to convert chemical energy to electrical Fei Shen climate change mitigation. This is particularly relevant reacted in a metathesis reaction, an epoxidation, a PhD energy or to store electrical charge. The core redox PhD

in the production of polymers, the vast majority of which cyclocarbonylation and an allylic rearrangement, the Funded by enzyme pyrroloquinoline quinone dependent glucose Funded by latter having been studied in detail with a palladium Innovation Fund dehydrogenase (glucose oxidization) and the copper China Scholarship catalyst to understand the mechanism. The alcohol has Denmark enzyme bilirubin oxidase (dioxygen reduction) Council been reacted with various electrophiles to form ethers, Supervisors were chosen as target enzymes. The enzymes were Supervisors esters and carbonates. In addition, the alcohol has been Robert Madsen immobilized on paper electrodes prepared from the Jingdong Zhang oxidized under mild conditions to the corresponding [email protected] conducting 2D-material graphene as anode and cathode, Jens Ulstrup ketone, which is a very unusual and reactive molecule. Esben Taarning respectively. Combining the two enzyme electrodes into [email protected] The ketone of MVG reacts readily in a Diels-Alder an electrical circuit with fuel supply directly from the reaction with dienes, thus forming new carbocyclic body’s own liquids then enables generating electricity as compounds. A number of these reactions with an enzymatic biofuel cell. Further integrating the redox MVG have been carried out on a large scale, and the protein cytochrome c on both electrodes as a charge- compounds have then been investigated as monomers for storing component, a fully operating self-charging the preparation of polymers by copolymerization with biosupercapacitor was fabricated. various reactive substrates. This diverse set of products Downstream products Schematic representation of the assembled ESBC. The structures of may support the implementation of MVG on the marked from MVG, the value cyt c (rust red), PQQ-GDH (purple) and BOx (green) correspond to tree of MVG. as an alternative to petrochemicals. PDB 1hrc, 1c9u and 2xll, respectively. Not drawn to scale.

Characterization and solution structure of multi-domain Novel tools for ultra-specific proteins and protein complexes targeting of nucleic acids

Protein-based therapeutics have become an essential for structural investigations using small angle X-ray Short synthetic oligonucleotides are valuable tools as investigation of their biophysical properties. The part of medical treatment. Despite all the advantages scattering. The results were combined with in-silico they find applications in numerous fields including findings confirmed the POCs ability for efficient target of protein-drugs, their stabilization is challenging. methods, such as MD simulation to provide a better nanotechnology, molecular biology, biotechnology, binding and single nucleotide polymorphism (SNP) Under inappropriate conditions, they might lose their understanding of stability on the molecular level. and clinical diagnostics. From a chemical standpoint, discrimination. Additionally, the serum stability studies activity and induce severe adverse effects. Stabilization Despite the common trends in stability, all studied oligonucleotides are polymers built of four nucleotide confirmed higher stability of the POCs when compared and formulation of protein-drugs is one of the most multidomain proteins show different behaviors, which molecules abbreviated A, T, C and G in deoxyribonucleic with the naked-parent oligonucleotides. Finally, critical, time-consuming and expensive steps in drug can be explained from the molecular structures and Alina Kulakova acid (DNA), and A, U, C and G in ribonucleic acid the research formulated complexed and conjugated Maria Taskova development. Many promising protein-drugs have interactions. Additionally, the dissertation shows that PhD (RNA). Oligonucleotide probes can be designed to oligonucleotide therapeutics with peptide sequences, PhD failed clinical trials due to their stability challenges. a combination of multiple methods leads to a better Funded by target any desired part of genome, using a fundamental designed to reduce the HIV1-mRNA or the BGas lnRNA Funded by Unfortunately, no general rules for the formulation understanding of protein stability. Marie Curie, Watson-Crick base-pairing rule, which is A binds T/U expression and function. The cell culture experiments 2/3 Villum Fonden process have been reported and it is not yet possible to EU, PIPPI and C binds G. However, translation from bench side showed promising effect and cell internalization for the 1/3 DTU Chemistry predict the behavior of different proteins under different Supervisors to practical applications requires the development of complexes and conjugates. Nevertheless, the variability Supervisors conditions. Pernille Harris chemically modified oligonucleotide sequences that within the quantitative results was high. Kira Astakhova This Ph.D. thesis is a part of the Protein-excipient [email protected] are gene specific, chemically, enzymatically stable, and In addition, a part of this PhD study concentrates on [email protected] Interactions and Protein-Protein Interactions (PIPPI) Anne Vindum Due efficiently internalized by target cells. the synthesis Mads Hartvig project, which goal is to improve the molecular This PhD study focuses on synthesis and characteriza­ of multi- Clausen Günther H.J. Peters [email protected] understanding behind protein stabilization and thereby [email protected] tion of new modified oligonucleotides as potent diagnostic fluorophore aid the formulation process. The focus of the PhD and therapeutic candidates. The project contributes with labelled work is investigation of the stability of three different several modifications that improve properties of short oligo­ types of multidomain proteins: transferrin, albumin- synthetic oligonucleotides. Given a broad applicability of nucleotides neprilysin fusion protein, and monoclonal antibodies. DNA and RNA analogues, this work might contribute to for detection All of them were systematically studied under different Different molecular advanced diagnostic and therapeutic tools. of mutated physicochemical conditions using high-throughput conformations of albumin- First, the study includes synthesis of a small library human siRNA mechanism techniques. These studies were used to choose conditions neprilysin fusion protein. of peptide-oligonucleotide conjugates (POCs) and genes. of action.

22 23 ANNUAL REPORT 2019 PHD DEFENCES

Femtochemistry and Laser Control Synthesis of biomass-containing xylan fragments and of Photochemical Reactions evaluation of ferulic acid esterase activity

The transformation of one set of chemical substances Through theory and computations, it is demonstrated Hemicellulose is a collection of polysaccharides with bound. First, the xylose units have been assembled (reactants) to another (products) is of fundamental how molecules can be rotationally and vibrationally complex structures that together with cellulose and into either tetra- or pentasaccharides using a selective importance for chemistry and biology. In a crude manner, excited. In a collaboration with an experimental group, lignin constitute the major constituent of biomass coupling method that allows the coupling of two traditional means as heat and light (i.e., temperature and the field-free rotational motion of I2 is analyzed. The (lignocellulose). The complex structure of hemicellulose thioglycosides with one another. Next, arabinose units frequency of photons) have been employed for decades to experimental observations show clear signatures of makes it difficult for enzymes to degrade biomass, which have been loaded onto the tetrasaccharides, while the guide the reactants into particular product channels. so-called quadrupole coupling to the nuclear spin is viewed as an important and CO2 neutral energy source pentaxylan has been coupled to two different glucuronic The atomic-scale dynamics of molecules and states and all features of this coupling are completely Esben Folger Thomas if properly utilized. acid units, giving a total of five synthetically made xylan Emilie Nørmølle chemical reactions unfolds on the femtosecond (10-15 accounted for. PhD The thesis first describes the synthesis of arabino- and fragments. Going forward, removal of the protecting Underlin PhD s) timescale and is governed by the principles of It is also shown how laser light can be used in optical Funded by glucuronoxylan fragments found in hemicellulose. These groups will yield the desired fragments that can be used quantum mechanics. These principles appear to offer the purification of a racemic mixture which is a 50/50 DTU Chemistry are of great interest as it is valuable to have access to pure to characterize hemicellulose enzymes. Funded by promise of a vastly improved performance over what is mixture of enantiomers, i.e., molecules which are each and well-defined fragments of hemicellulose that can be Another project in the dissertation was completed DTU Chemistry Supervisor achievable within the classical framework of so-called other’s mirror images. In order to close the gap between Niels Engholm used as substrates for hemicellulose-degrading enzymes during an external stay at Wageningen University Supervisor incoherent processes. To that end, photochemistry with theory and experiment, the optimized laser-light pulses Henriksen such as xylanases, arabinosidases and glucuronidases. and Research. Here, work has been done on the Robert Madsen coherent laser light is a potential quantum technology are constructed in similar way as in pulse shapers that [email protected] The synthesized fragments consist of composite xylose characterization of ferulic acid esterases, which form an [email protected] that is a potentially attractive alternative to classical are used units to which either arabinose or glucuronic acid are important part of the arsenal of hemicellulose-degrading photochemistry. in expe­ enzymes, as these can cleave the ester bond between The PhD thesis investigates the interaction between rimental ferulic acid and polysaccharides. Thus, these enzymes laser light and molecules in the regime of the so-called setups. may reduce some of the complexity of the hemicellulose non-resonant dynamic Stark effect. This amounts to a structure. However, these enzymes show considerable time-dependent modification of the interaction potential differences in reactivity and specificity, which is why it determined by the pulse envelope of laser pulses and has been investigated whether a previously published independent of laser frequency. The lack of frequency classification based on the genomes can be related to the dependence is a very convenient feature for experimental Sketch of a closed-loop specific reactivity. This was investigated via the release implementations. control system. of ferulic acid and diferulic acids from several different types of natural biomass substrates. This showed that two classes of enzymes in particular were very active.

Heatmap for the release of FA and pCA from the natural substrates tested, the results are shown as percentages of bound Development of Zeolite Catalysts and Processes for content (0 – 100 %) as measured by UHPLC-UV. CS: corn stover; the Selective Conversion of Sugars to Bio-Polymer Monomers WS: wheat straw.

Our current society is highly dependent on non-renewable and the essential structural properties for obtaining materials derived from fossil sources, which upon extrac­ high catalytic activity are elucidated. Finally, the tion and refining cause net green-house gas emission to project considers the production of a new bio-based the atmosphere, resulting in environmental issues such as product, methyl vinyl glycolate (MVG), obtainable from climate change. Polymers represent ubiquitous products glycolaldehyde formed from sugars. The MVG molecule in daily life and constitute most of synthetic materials. The contains functionalities appropriate for representing production of polymers from renewable biomass resources a building block for the production of new bio-based Irene Tosi is possible, but technologies are immature for making polymeric materials. PhD these bio-based products commercial realities competitive In summary, the thesis provides important insight Funded by with fossil-based materials. into existing and new processes for the conversion of Innovation Fund The thesis explores processes for the conversion renewable sources into chemical products, and conveys Denmark of biomass sources with solid zeolite catalysts into useful information for the development of technologies Supervisors chemical building blocks useful for the production of potentially replacing the refining of fossils. Anders Riisager polymeric materials. In particular, different sugars are [email protected] used as starting substrates. The project also investigates Esben Taarning the pathways for the transformation of sugars and the parameters affecting the productivity, achieving deep understanding of the studied reactions and optimized conditions. The parameters for the production of methyl lactate - the monomer of polylactic acid, the most common bio-based biodegradable plastic - starting from Spectral region of the primary alcohols common sugars were optimized. Part of the thesis is of 1H-13C HSQC spectra, signals dedicated to the study of the zeolite catalysts. of the different forms of methyl The synthesis of the catalytic materials is investigated, fructosides and methyl glucosides.

24 25 ANNUAL REPORT 2019 PUBLICATIONS

Master Theses Publications 2019 2019

Ahmad Kasem Haidar Jonas Himmelstrup Mikkel Rytter Ottosen DTU Chemistry has a high performance in Synthesis of analogues of a lead Development and Study of New Reactions Chemoenzymatic Dynamic Kinetic the world of chemical science. This is reflected compound with anti-seizure activity with Homogeneous Metal Catalysis Resolution of 2-Functionalized Aldehydes' in all the publications produced and published in high impact journals every year. In this Alejandro Ventura-Traveset I Julve Josefine Hvarregaard Andersen Nikolaos Dimitrios Psaraftis Annual Report, you can find examples of some In vitro activity of GPCR modulators Derivation and implementation of coupled Novel gene therapeutic for treatment of the Department's exciting results and cluster linear response in the molecular- of Dementia with Levy Bodies projects during 2019. The Department has a Alessio Radaelli orbital-based coupled cluster code eT strong track record in scientific publications Strain-Release Driven Cycloadditions Oliver Sørensen Siig and we keep increasing the ISI publications. Kasper Alexander Brauner Hansen Computational studies of the reactivity For a complete list of the publications in 2019, Ana Laura Rodrigues da Silva Hydroformylation in gas-phase with of different sites in a deNOx catalyst please scan the code or visit: Fragment-based Drug Discovery supported ionic liquid phase (SILP) kemi.dtu.dk/english/aboutus/publications. catalyst systems Rasmus Lykke Mortensen Beatrice Flohr Schultz Synthesis, Characterization, and Testing Kinetic characterization of TPH1 variants Kasper Juul Møller of Novel Cross-Linked Polystyrene Materials combined with molecular dynamics Validation of ICP-OES method for assay for Catalytic Hydrogenation of CO2 to simulations of pharmaceutical raw material Formic Acid

Caroline Grønbech Hansen Kianoosh Moeini Stanislav Molodtsov Analysis of natural products from Geothermal Energy Production Synthesis of nickel nanoclusters in the fish killing microalgae Prymnesium and Heat Storage Potential of zeolites for application as heterogeneous polylepis and Karlodinium armiger Frederikshavn Formation catalysis in the MTG reaction

Christina Sophie Haxvig Kitti Szabo Tine Marianne Duus Advanced linker technologies for Design and synthesis of Sequence-dependent conjugation strategy antibody-drug conjugates novel GLP1 variants for site-selective protein modification

Christine Thue Poulsen Lasse Johansen Umar Fayyaz Synthesis of a natural product-derived Iron-Catalyzed Dehydrogenation Investigation of the effect of electrolyte compound collection of Alcohols activities on the recovery of oil in chalk by imbibition Ida Marie Vedel Mette Elmegaard Andersen Kinetic characterization of tryptophan Development of New Reactions with Yemily Luciana Mouret hydroxylase isoforms Homogeneous Metal Catalysis Hydraulic fracturing in chalk reservoirs under variable stresses Jesper Uhd Mette Eybye Lindén Sequence-dependent conjugation Investigation of the ability of acylated strategy for site-selective protein peptides to oligomerize and to bind to modification human serum albumin

Find DTU Chemistry Students at: facebook.com/DTUChemistryStudents For more information: Teaching Administrator Mette Christine Møller, [email protected]

26 27 ANNUAL REPORT 2019 HIGHLIGHTSEVENTS 20192018 Events Open House Industry Project Day

The Department is always very active at DTU's annual Open The Department hosted two Industry Project Days where House event. At the information stands, students, faculty, and industrial partners had the opportunity to present potential Heads of Studies Klaus B. Møller and Mads H. Clausen all projects to BSc, BEng, and MSc students from DTU Chemistry. answered questions from curious high school students. Several companies such as Zealand Pharma, Aquaporin, Around 137 potential students participated in the Chemistry Novozymes, Haldor Topsoe, and Synopsys Denmark participated and Technology guided tours, and the effort was not in vain with interesting proposals and interacted with the students. Due – 88 students were signed up for the BSc programme. Human to the success of the events, more Industry Project Days will be Life Science Engineering had 68 participants at the guided arranged in the future, and DTU Chemistry look forward to tours and 60 students signed up for the programme. seeing even more companies joins.

PhD Symposium REACHING OUT

The 2019 edition of the PhD Symposium - held at Konventum, ScienceShow Elsinore - was filled with interesting presentations and posters. Head of Department Erling H. Stenby presented two DTU ScienceShow is a group of students who deliver a awards during the symposium: Natalia Teresa Skawinska professional science show with entertaining and educational won ‘Best Oral Presentation’ for her presentation of “Towards elements from chemistry and physics. DTU ScienceShow is part the structure of human tryptophan hydroxylase isoform 2” of DTU’s branding and recruiting strategies and locally hosted and Laura Voigt won ‘Best Poster Presentation’ for her poster at DTU Chemistry with Professor Anders Riisager heading titled “Low valent metal-organic frameworks”. the Advisory Board. In 2019, ScienceShow was busy with 90 shows all over Denmark – mainly entertaining high school and primary school students. The show also performed at big events such as Folkemødet (Denmark’s Democratic Festival), Science Expo, and European Science Fair.

The Danish Chemistry High School Lectures

Olympiad DTU Chemistry hosts a broad range of lectures for high school students. In 2019, 1153 high school students have participated DTU Chemistry hosted the 4th round of the Danish in lectures such as Spectroscopy and Identification of Organic Chemistry Olympiad. Associate Professor Susanne Mossin substances. and chemistry student Sofie H. Pedersen had put together an exciting programme for the visiting finalists. During the three days at DTU, the students experienced inspiring lectures from several researchers and had theoretical and practical tests. After a selection process, four students represented Denmark at the IChO (International Chemistry Olympiad) in Paris. The team won one gold and three bronze medals.

28 29 ANNUAL REPORT 2019 HIGHLIGHTS 2019

DTU Chemistry has selected various highlights from 2019 to supplement the articles on pp. 6-15. You can read more at our website kemi.dtu.dk/English/Nyheder, or follow us on linkedin.com/company/dtu-kemi. Highlights

GRANTS & HONOURS reversible formation of glycosidic linkages be developed for the dehydrogenation technology for advanced downstream SNIFFER detection of improvised explosives. between unprotected monosaccharides of alcohols and the hydrogenation of processing by combining catalytic synthesis The overall objective of the project is to make The Novo Nordisk Foundation and generate dynamic mixtures of oligo­ unsaturated functional groups. with the corresponding separation units in the world a safer place for the public, by Professor Mads H. Clausen and co-applicant saccharides under thermodynamic control. a single highly efficient catalytic membrane developing an easy to use handheld detector, Assistant Professor Luca Laraia was awarded Ultimately, this will make industrial In another project, Mads H. Clausen aims reactor (CMR). This disruptive technology wwhich can detect improvised explosives 10.6 MDKK by the Novo Nordisk Foundation production methods more sustainable by to develop new glycan-based cancer vaccine has the ability to e.g. reduce greenhouse gas and precursors. The portable SNIFFER will for establishing a new research infrastructure reducing the emission of greenhouse gases candidates for improved immunotherapy, emissions of large volume industrial process detect improvised explosives and precursors called DTU-ScreeningCore. The aim and lowering energy and water usage, because which the Independent Research Fund by up to 45 % and will be further developed for improvised explosives. The sniffer system of DTU-SCore is to provide extensive enzymatic processes are fast, specific and Denmark chose to grant 2.4 MDKK. in this project. The MACBETH consortium includes the following components: Air small molecule screening capabilities for take place under mild conditions in water. Immunotherapy is currently revolutionizing consists of 25 partners, with Evonik sampling, Sensor system with colorimetric bio­chemical and cellular assays. The core cancer therapy by harnessing the power of Performance Materials as consortium lead. chip cassettes, Monitoring station with facility will be a unique high-throughput The Carlsberg Foundation the immune system against cancer cells. signal processing software, secure wireless screening platform at a Danish university Associate Professor Sophie Beeren received The identification of tumour associated Anders Riisager has also received 4.44 communication between SNIFFER and and will be open access with a mission 4.5 MDKK from the Carlsberg Foundation: carbohydrate antigens (TACAs), aberrant MDKK for a future Marie Skłodowska- monitoring station. to advance biomedical research, serving Young Researcher Fellowship for her types of glycans decorating tumour cells, Curie Innovative Training Network called as a starting point for chemical biology research in sustainable enzymatic processes. has paved the way for the development of Coordination Chemistry Inspires Molecular research and early drug discovery. The cancer vaccines. Based on the hypothesis Catalysis (CCIMC EJD). The network platform will integrate with the current The Carlsberg Foundation has also awarded that fully glycan based cancer vaccines can addresses the current lack of coordinated DK-OPENSCREEN infrastructure and three researchers with infrastructure grants. represent a way to improve active cancer doctoral training at the European level on e.g. offer automation for liquid and plate Associate Professor Susanne Mossin received immunotherapy, the research approach molecular catalysis. It aims to push the handling. According to Professor Mads H. 250,000 DKK for a mass spectrometer will include the preparation of vaccine frontiers of knowledge in ligand design, Clausen DTU-SCore will perform its first for operando spectroscopy – enabling candidates based on ganglioside TACAs coordination chemistry, precatalyst demonstration projects in 2021. simultaneous evaluation of both structure that are easy to formulate and able to elicit development, catalyst recovery and catalytic and activity of e.g. a catalyst in action. The an immune response independent from process implementation, while also offering Assistant Professor Luca Laraia also received second recipient, Assistant Professor Luca individual polymorphisms. full scale training in professional and 2.1 MDKK for the research project ‘Blocking Laraia, was granted 190,000 DKK for a personal transferable skills, to prepare a cholesterol production through specific state-of-the-art imaging system for chemical Assistant Professor Luca Laraia received new generation of junior scientists to meet protein degradation’. Diseases originating biology. Finally, the Carlsberg Foundation two large grants from the Independent the economic and societal challenges of the from the mis-regulation of cholesterol awarded Professor Mads H. Clausen 734,900 Research Fund Denmark. The first chemical industry in the 21st century. To homeostasis are a significant burden on DKK to support the new aforementioned project was awarded 2.87 MDKK and achieve these objectives, a consortium of society. Although statins are widely used DTU SCore infrastructure. aims to develop a general approach to 9 academic beneficiaries from 7 European to lower blood cholesterol levels, their identify oxysterol-interacting proteins by countries will recruit 15 doctoral students extended use can result in overexpression Independent Research Fund combining induced protein degradation to work on coordinated projects in close of their target protein HMG-CoA reductase Denmark with high resolution, proteome-wide cooperation with the industrial sector. (HMGR), in a compensatory mechanism. By Professor Robert Madsen has been awarded mass spectrometry. The second project using the recently developed strategy termed 2.88 MDKK from the Independent ‘Unravelling the sterol-interacting proteome Postdoc Cecilia Romano was awarded proteolysis targeting chimera (PROTAC), Research Fund Denmark for developing using limited proteolysis small molecule’ a 1.55 MDKK Marie Skłodowska-Curie the Laraia Lab aims to design ligands of ‘Chromium-Catalyzed (De)Hydrogenation was granted 2.87 MDKK. Individual Fellowship for her research cholesterol biosynthetic enzymes that cause Reactions’. Reactions with hydrogen gas within ARGONAUT: from the synthesis of protein degradation, rather than inhibition. constitute the most important catalytic EU Horizon 2020 gAnglioside tumouR antiGens to a platfOrm transformations in organic chemistry. Professor Anders Riisager, MACBETH for caNcer Active. The Novo Nordisk Foundation granted Unfortunately, homogeneous catalysts for consortium partner from DTU Chemistry, Associate Professor Sophie Beeren 2.87 these transformations are based on precious has received 5.2 MDKK from EU Horizon The Danish Ministry of Defence MDKK for a research project that combines platinum group metals or other expensive 2020 under the grant type SPIRE – Associate Professor Mogens Havsteen enzymology with supramolecular chemistry. metal complexes. In this project, inexpensive Industrial Sustainability. The MACBETH Jakobsen received 2.47 MDKK from the She will exploit enzymes to catalyse the and non-toxic chromium catalysts will consortium provides a breakthrough Danish Ministry of Defence for ‘portable

30 31 H 32 ANNUAL REPORT 2019 their theses. theses. their on percent 100 focus to them –enabling DKK 35,000 awarded be will Both sciences. natural the in students master talented most country's the to awarded is which scholarship, Foundation Nordisk Novo the receive to selected been have Tobiasand Hansen, Nørby Tjørnelund Helena Damtoft students, Two master talented Media’.in Porous Flow of Simulation Thermal for Compositional Modelling EoS and Computation ‘Flash for Paterson Duncan and Solution’ in Dynamics Molecular on work ‘Photoinduced for his Levi Gianluca selected. was Chemistry DTU from Paterson Duncan and Levi Gianluca of theses 2019,In the Theses’. ‘Springer series portfolio scientific the in for publication thesis PhD best their select annually institutes research top-ranked Internationally AND HONOURS OTHER GRANTS years. 20 for almost chemistry organic in courses introductory the –taught courses other –among has Madsen honor. Robert distinguished of the recipients the one of was Chemistry DTU from Madsen Robert Professor Year', 2019, in of the and 'Lecturer as lecturers two honors annually Forening why is Polyteknisk That teachers. class world- you need engineers, world-class educate to order In of the year' award receives 'Lecturer Madsen Robert ighlights

from DTU Chemistry. DTU from Madsen Robert Professor Year 2019: the of Lecturer

Photo: Ulrik Jantzen

Photo: Ulrik Jantzen Key numbers Key a record number of PhD students in 2019. in students of PhD number a record hired Department the again, Once talent. PhD new with flourishing are groups research Our scientists. future bright, for the choice apopular is Studies of Head as Clausen H. Mads Professor with Engineering Science Life Technology, Human and Chemistry 2019.in like Just expanded also Chemistry Applied in programme MSc The 88. to 72 from accept we can of applicants number the expanded recently Chemistry DTU Accordingly, Technology. and Chemistry in BSc for the of applicants number high aconsistent had years in recent have We talent. scientific attracting in successful very still is Chemistry DTU Chemistry. atDTU activities the in interest increasing take foundations private and companies, private funds, public as such DTU outside sources that 2019. find to in We pleased are funding for external applications in rate success high a had Department The department. research aleading remain to order in and results projects, people, through excellence on scientific focuses Chemistry DTU Research Leading A Department Students Students Students Students Students Students MDKK MDKK 2015 2015 2015 2015 2015 2015 2015 2015 58 58 68 68 42 42 8 8 PhD admission MSc admission 2016 2016 2016 2016 2016 2016 2016 2016 38 38 21 21 84 84 59 59 External funding External funding External PhD admission PhD PhD admission PhD MSc admission MSc admission MSc BSc admissionBSc admissionBSc 2017 2017 2017 2017 2017 2017 2017 2017 44 44 70 70 22 22 72 72 2018 2018 2018 2018 2018 2018 2018 2018 41 41 24 24 72 72 59 59 2019 2019 2019 2019 2019 2019 88 88 66 66 53 53 26 26 2019 2019 60 60 Students Students Students Students Students Students MDKK MDKK 2015 2015 2015 2015 2015 2015 2015 2015 58 58 68 68 42 42 8 8 External funding External BSc admissionBSc 2016 2016 2016 2016 2016 2016 2016 2016 38 38 21 21 84 84 59 59 External funding External funding External PhD admission PhD admission PhD MSc admission MSc MSc admission MSc BSc admissionBSc admissionBSc 2017 2017 2017 2017 2017 2017 2017 2017 44 44 70 70 22 22 72 72 2018 2018 2018 2018 2018 2018 2018 2018 41 41 24 24 72 72 59 59 2019 2019 2019 2019 2019 2019 88 88 66 66 53 53 26 26 2019 2019 60 60 Human Life Science Engineering andChemistry Technology HIGHLIGHTS 2019 HIGHLIGHTS 33 ANNUAL REPORT 2019 DTU STAFF 2019

Acknowledgement Obituary for Professor Jingdong Zhang

DTU Chemistry highly Christine Weber Ole Kirk Lundbeck A/S Novozymes A/S appreciates the active On Thursday, 9 January 2020, Professor Six or seven years ago, Jingdong launched involvement of our Jingdong Zhang passed away after a long a new research program, "Untraditional Hanne B. Rasmussen Jesper Nerlov period of serious illness. Jingdong's death Nano­materials in Electrochemistry Advisory Board: Novo Nordisk A/S Haldor Topsoe A/S is a huge loss for her family, colleagues, and and Bioelectrochemistry", focused on students at DTU Chemistry. She was just 51 electrochemical surfaces of graphene, years old. metallic nanoparticles and their Tue Johannessen combinations. She progressed very far in Amminex A/S In the later 20th century, electrochemistry combining this new materials science with underwent a renaissance by introducing new electrochemistry of both enzymes and methods of solid-state and surface physics, entire bacterial cells, even constructing not least due to scanning tunneling and working bio-electrochemical sensors and atomic force microscopy. Professor bio-fuel cells. Jingdong Zhang mastered “the new electrochemistry”. Over the years with Until the very end, Jingdong was an Albeda Research LAB DTU Chemistry has a wide Jingdong as a strong driving force, extremely active and inspiring supervisor cooperation with industry. Albumedix Leapcraft her group at DTU Chemistry and an accomplished and well-liked Allegan plc Leo Pharma developed the entirely new lecturer in our undergraduate courses. As Among the Department’s Alumichem Linde concept "Single-molecule you approached her classrooms, you would Electrochemistry of always be delighted to hear her enthusiastic industry partners are: Liqtech International Amminex complex molecules teaching style. Arla Lloyds Register Consulting and biomolecules", Arrayjet Lundbeck now broadly Professor Jingdong Zhang will be missed adopted by by us all. Bayer MedImmune research groups Bioenergy 2020+ NanoTemper Technologies in Europe and Biolin Scientific Niels Clauson-Kaas the USA. Jens Øllgaard Duus, Carlsberg Novo Nordisk Erling Halfdan Stenby, and Jens Ulstrup Coloplast Novozymes ConocoPhillips Perstorp Department of Chemistry CP Kelco PlantProbes CrimTrack Aps Pharmacosmos Danish Power System QuantiBact Edelris RePhos Equinor Riemann European Membrane House Scandinavian Micro Biodevices Jingdong Zhang Evonik Industries SSI Diagnostica ExxonMobil Total 1992 MSc in applied chemistry Ferring Umicore Denmark Aps from Shanghai University 1996 PhD in analytical chemistry GlycoSpot Veloxis from Changchun Institute Grundfos Wärtsilä Puregas Solutions of Applied Chemistry Haldor Topsøe Welltec 2016: Professor of inorganic chemistry at DTU Chemistry. Hempel Wyatt Technology Europe GmbH Johnson Matthey Ørsted Junckers Industrier A/S

34 35 ANNUAL REPORT 2019 DTU STAFF 2019

DTU Chemistry Staff

Head of Department Erling H. Stenby, Professor [email protected]

ORGANIC AND INORGANIC CHEMISTRY PHYSICAL AND BIOPHYSICAL CHEMISTRY

Head of Section Head of Section Jens Ø. Duus, Klaus B. Møller, Professor Professor [email protected] [email protected]

Faculty Faculty Anders Riisager, Kasper Steen Pedersen Mads H. Clausen, Robert Madsen, Esben Thormann, Kasper Planeta Kepp, Niels Engholm Henriksen, Sokol Ndoni, Professor Assistant Professor Professor Professor Professor Professor Associate Professor Senior Researcher [email protected] [email protected] [email protected] [email protected] [email protected] [email protected] [email protected] Sonia Coriani, Charlotte Held Gotfredsen, Katrine Qvortrup, Martin Nielsen, Sophie Beeren, Günther H.J. Peters, Kenny Ståhl, Pernille Harris, Professor Associate Professor Assistant Professor Assistant Professor Associate Professor Professor Associate Professor Professor [email protected] [email protected] [email protected] [email protected] [email protected] [email protected] [email protected] [email protected] Wei Yan, David Ackland Tanner, Kira Astakhova, Mogens Havsteen Jakobsen, Susanne Lis Mossin, Irene Shim, Kristoffer Almdal, René Wugt Larsen, Senior Researcher Professor Associate Professor Associate Professor Associate Professor Associate Professor Professor Associate Professor [email protected] [email protected] [email protected] [email protected] [email protected] [email protected] [email protected] [email protected] Jingdong Zhang, Luca Laraia, Rasmus Fehrmann, Søren Kegnæs, Professor Assistant Professor Professor Professor [email protected] [email protected] [email protected] [email protected]

Scientific Staff Rosa Maria Padilla Paz, Postdoc Huili Cao Samuel Gilbert Elliot Scientific Staff PhD Students Sowmya Indrakumar Other staff Sangita Khatri, Research Assistant Irene Tosi Simone Louise Zacho Sujata Mahapatra Ahmad Kasem Haidar, Research Sebastian Meier, Senior Researcher Jakob Maximilian Marinkovic Simone Vestermann Samuelsen Alina Vitaliyivna Kulakova, Postdoc Anders Ørts Tjell Suk Kyu Ko Maria Blanner Bang, Assistant Søren Kramer, Assistant Professor Jie Meng Sofie Slott Budheswar Dehury, Postdoc Alexandre Paolo Voute Tao Jiang Academic Assistant Anders Højgaard Hansen, Postdoc Christos Tsanas, Postdoc Anna Kristina Schnack-Petersen- Xinxin Xiao, Postdoc Jing Tang Sol Laura Gutierrez Alvarez Torsha Moitra Mariusz Kubus, Cecilia Romanó, Postdoc Diego Rolando Sandoval Lemus, Christin Pohl Viola Previtali, Postdoc Kai Gao Thomas Edward Whitmarsh-Everiss Ulf Molich Academic Assistant Cecilia Rossetti, Postdoc Katja Desiree Pedersen Wei Huang Postdoc Daniel Hansen Xinyue Li Christian Engelbrekt, Researcher Katja Egeskov Grier Weiguang Jin Diptesh Dey, Postdoc Daniil Fedotov Yibo Yang Christian Kjeldsen, Postdoc PhD Students Kristoffer Hauberg Møller Wenting Fang Duncan Paterson, Postdoc Fatemeh Keshavarzi Yiqun Liu Danielle Lobo Pinheiro Nielsen, Laura Voigt Xianyi Cao Kalyanashis Jana, Postdoc Fernando De Azevedo Medeiros Amalie Nørskov Postdoc Luca Piccirilli Xiaomei Yan Mátyás Imre Pápai, Researcher Frederik Hegaard Anders Øwre Dennis Larsen, Postdoc Maria Taskova Yulong Miao Octav Caldararu, Postdoc Ida Marie Vedel Andreas Kjær Erichsen Elisa Sassetti, Postdoc Mathias Thor Nielsen Zhenwei Ni Pernille Sønderby, Postdoc Johannes Eiler Bo Michael Jessen Hao Jiang, Postdoc Mathies Brinks Sørensen Zhiyong Zheng Peter Westergaard Jakobsen, Josefine Hvarregaard Andersen Charlotte Nybro Dansholm Jerrik Jørgen Mielby, Researcher Mike Steffen Bernhard Jørgensen Researcher Junhao Huang Charlotte Uldahl Jansen Jesper Uhd, Research Assistant Mikkel Krell-Jørgensen Rasmus Faber, Postdoc Junjie Kang Chengxin Li Jonas Hansen, Postdoc Mikkel Burggraaf Buendia Other staff Rukmankesh Mehra, Postdoc Klaus August Moltved David Nielsen Kaibo Zheng, Senior Researcher Mingli Liang Saeed Zajforoushan Moghaddam, Koosha Ehtiati David Benjamin Christensen Faranak Nami, Kobra Azizi, Postdoc Nianzhe He Postdoc Line Abildgaard Ryberg Emilie Nørmølle Underlin Platform Engineer Leonhard Schill, Postdoc Nicolai Steen Broberg Hansen Sarah Hedberg, Postdoc Marta Lopez Vidal Fabrizio Bottaro Lilja Kristinsdottir, Postdoc Niklas Rosendal Bennedsen Julie Højstrup Shota Tsuru, Postdoc Mostafa Abedi Fabrizio Monda Morten Gotthold Vinum, Research Nikolaj Sten Troelsen Student Assistant Teresa Regueira Muñiz, Researcher Natalia Teresa Skawinska Faliu Yang Assistant Peter Andreas Boeg Tine Maja Frimann, Postdoc Robert Andrew Biro Fangyuan Diao Kasper Enemark-Rasmussen Nasrin Nemati, Research Assistant Ping Zhu Yi Yang, Assistant Professor Runtian Qie Farnoosh Goodarzi NMR Technician Ning Tang, Postdoc Qian Zhao Fei Shen Olga Gordivska, Postdoc Qinying Pan Lisa-Marie Jaunet, Frederick Stappen Nielsen Petya Popova, Research Assistant Rouzana Pulikkal Thumbayil Student Assistant Giorgia Masciotta Rebecka Maria Larsen Werchmeister, Sakhitha Koranchalil Senior Researcher Hua Chen

36 37 ANNUAL REPORT 2019

DTU Chemistry Staff

DTU Chemistry TECHNICAL AND ADMINISTRATIVE STAFF Annual Report 2019

PUBLISHER Head of Administration DTU Chemistry Building 207 Inge Holkmann Olsen DK-2800 Kgs. Lyngby Phone: +45 45 25 24 19 [email protected] Email: [email protected] Website: www.kemi.dtu.dk

EDITOR-IN-CHIEF Administration Laboratory Manager Peter Køhne Henriksen, Reception Erling H. Stenby, Laboratory Technician Head of Department, Jakob Espersen, Bodil Fliis Holten Jette Berg Nestén, DTU Chemistry Communications Officer [email protected] Philip Charlie Johansen, Receptionist Laboratory Technician EXECUTIVE EDITOR Josefine Flanagan Lønholdt, Lillian Karen Holm, Jakob Espersen, Research Support Advisor Anne Hector, Receptionist Communications Officer, DTU Chemistry Laboratory Technician Kristine Albrektsen, Chief Operating Officer Monica Esterajher TEXT Research Support Advisor Anna-Lisbeth Dorthea Riber, Jimmie Thomsen Søndergaard, Jakob Espersen, Laboratory Technician [email protected] Receptionist Communications Officer, Maria Bundgaard, DTU Chemistry Personal Assistant, Betina Margrethe Morten Andersen, ScienceShow Manager Farrington Roesdahl, Bente Hviid, Science Reporter, manjourn.dk Laboratory Technician Administrative Assistant Mette Christine Møller, LAYOUT Administrative Coordinator Brian Brylle Dideriksen, John Nissen, We Love People Laboratory Technician Service Assistant Mette Hansen, PHOTOS Coordinator David Frej Nielsen, Lars Egede Bruhn, Jakob Espersen Laboratory Technician Service Assistant We Love People Ulla Vig Nissen, Greg Stewart/SLAC Research Support Advisor Ea Judith Larsen, Stephan Jean Jeannenot Ulrik Jantzen SLAC National Accelerator Laboratory Laboratory Technician Galsøe, Service Assistant Shutterstock unless otherwise stated IT Manager Johanne Marie Nielsen, Thomas Bachau Pedersen, Laboratory Technician Service Assistant PRINT Bo Sørensen Rosendahls [email protected] Lise-Lotte Jespersen, Laboratory Technician Machine Section ASSISTANT EDITORS Inge Holkmann Olsen, Jonas Jan Mansoor, Lise Lotte Berring, Andreas Graff Pedersen, Head of Administration, DTU Chemistry IT Supporter Laboratory Technician Assistant Engineer Klaus B. Møller, Ishaq Khaliqdad, Head of Section, Kenneth Pihl Aamand, Marie Koefoed, DTU Chemistry IT Supporter Laboratory Technician Industrial Technician Jens Ø. Duus, Head of Section, DTU Chemistry

EDITORIAL SUPPORT Maria Bundgaard, Trainees Other Staff Mette Hansen, Mette Christine Møller, Burak Yildiz, Peter Mayland Madsen, Anne Glavind, Oliver Zinck Henriksen, Rasmus Wochnik Aniol, IT Supporter IT Supporter Student Assistant Student Assistant Josefine Flanagan Lønholdt, Camilla Lyngsie Morsing, Rasmus Wochnik Aniol, Louise Linddal Bitz, Tai Hung Van, Kristine Albrektsen, Laboratory Technician Office Trainee Student Assistant Student Assistant Oliver Zinck Henriksen, Kenneth Pihl Aamand, Morten Fuglsang Andersen, Thomas Stubkjær, Nanna Fossdahl Prehn, Victor Einer Wiggers, Bo Sørensen Industrial Technician Industrial Technician Student Assistant Student Assistant – all from DTU Chemistry

38