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Cascade Catalysis–Strategies and Challenges En Route to Preparative

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Cascade Catalysis–Strategies and Challenges En Route to Preparative ChemComm Accepted Manuscript This is an Accepted Manuscript, which has been through the Royal Society of Chemistry peer review process and has been accepted for publication. Accepted Manuscripts are published online shortly after acceptance, before technical editing, formatting and proof reading. Using this free service, authors can make their results available to the community, in citable form, before we publish the edited article. We will replace this Accepted Manuscript with the edited and formatted Advance Article as soon as it is available. You can find more information about Accepted Manuscripts in the Information for Authors. Please note that technical editing may introduce minor changes to the text and/or graphics, which may alter content. The journal’s standard Terms & Conditions and the Ethical guidelines still apply. In no event shall the Royal Society of Chemistry be held responsible for any errors or omissions in this Accepted Manuscript or any consequences arising from the use of any information it contains. www.rsc.org/chemcomm Page 1 of 15 ChemComm ChemComm RSCPublishing Feature article Cascade catalysis – strategies and challenges en route to preparative synthetic biology Cite this: DOI: 10.1039/x0xx00000x Jan Muschiol,a,+ Christin Peters,a,+ Nikolin Oberleitner,b Marko D. Mihovilovic,b Uwe T. Bornscheuera and Florian Rudroffb,* Received 00th January 2012, Accepted 00th January 2012 Nature’s smartness and efficiency assembling cascade type reactions inspired biologists and chemists all around the world. Tremendous effort has been put in the understanding and DOI: 10.1039/x0xx00000x mimicking of such networks. In recent years considerable progress has been made in www.rsc.org/ developing multistep one-pot reactions combining either advantage of chemo-, regio-, and stereoselectivity of biocatalysts or promiscuity and productivity of chemocatalysts. In this context several concepts, inspired by different disciplines (biocatalysis, metabolic engineering, synthetic chemistry, material science), have been evolved. This review will focus on major contributions in the field of cascade reactions over the last three years. Manuscript Accepted ChemComm This journal is © The Royal Society of Chemistry 2013 Chem. Comm., 2014, 00, 1-3 | 1 ChemComm Page 2 of 15 ChemComm RSCPublishing Feature article A Introduction compartmentalisation by nanoparticles,7 protein scaffolds10 or immobilisation.8 Nature has evolved a highly efficient system in form of cascade Nevertheless, a successful cascade type reaction requires reactions which assemble the metabolic networks that ensure optimized reaction parameters and a perfect process control. life (growth and survival).1 In a living cell, basically a one-pot Despite compatible temperature, solvent, and pH, a central system, these multistep reactions are catalysed by numerous issue in such reactions is the imbalance due to different enzymes fine-tuned by evolution in an aqueous environment. enzyme/catalyst properties. Inspired by the systems biology Mimicking this natural system in chemical synthesis and community a rather new approach to maximize the efficiency performing catalytic cascade reactions in a one-pot manner was of multi-enzyme processes by building kinetic models to intensively investigated over the past decades.2 optimize stoichiometry was developed.11 For another strategy to Multistep cascades in living organisms commonly function enhance synthetic multi-enzyme cascade reactions nature without separation of intermediates; concentrations of all provided the blue-prints with substrate channelling along reactants are kept low, which allows high selectivity and avoids spatially organized multi-enzyme structures. Efficient through- by-product formation. Taking nature as a model, application of put is achieved by facilitated transfer of a reaction intermediate cascade reactions in organic synthesis offers a lot of advantages from the active site of one enzyme to the active site of a over the classical step-by-step approach. As there is no need for downstream enzyme without first diffusing into the bulk Manuscript purification, operating time, costs and waste are reduced, atom solution. Due to new developments in nucleic acid economy and overall yields are improved. Additionally, the nanotechnology this system can be mimicked through protein problem of unstable or toxic intermediates can be overcome scaffolding.12 and reactivity and selectivity can be enhanced by evading Recent research also offers possibilities for environmentally equilibrium reactions by the cooperative effect of multiple benign developments. With a multi-enzyme cascade system catalyst.3-5 based on ultrathin, hybrid microcapsules carbon dioxide Although significant research progress was achieved over the conversion to methanol could be achieved.13 Protein and past decades, one-pot multistep reactions are still not of general metabolic engineering in line with a systematic study of applicability in chemocatalysis due to problems with pathway bottlenecks accomplished the biodegradation of highly compatibility of reaction conditions.2 Biocatalytic cascades are toxic halogenated compounds to glycerol in E. coli.14 Accepted easier to realize as most enzymes reach their catalytic optimum It becomes clear that a multidisciplinary approach is aspiring at at similar temperature and pH conditions in aqueous buffers (of the process design of efficient one-pot multistep reaction compatible salt activities). Additionally, biocatalysis is cascades.2 Most recent developments highlighting different nontoxic and enzymes are highly chemo-, regio-, and concepts in the academic area shall be presented here. stereoselective.6 Bio- as well as chemo-catalytic cascades, generally described B In vitro cascades/ Protein engineering as a consecutive series of chemical reactions proceeding in Biocatalytic cascade reactions have recently attracted concurrent fashion,7 are often classified in groups. In domino significant attention enabling multistep transformations in one- reactions one catalyst triggers the formation of a reactive pot thereby circumventing the isolation of (unstable or toxic) intermediate, which undergoes spontaneous transformation. intermediates. Generally, in vitro cascades were performed Cascades with two or more catalysts can be performed in either with purified enzymes, crude cell extracts (CCE), resting ChemComm sequential or simultaneous mode. Whereas in simultaneous (or cells or lyophilized recombinant cells. The scope of cascade relay) cascades all the catalysts and reactants are present from reactions so far known in literature last from simple the outset, in the sequential approach the next catalyst is added combinations of one enzyme with a cofactor recycling system only after the completion of the previous step.4 to coupling of thirteen different enzymes.15 Alcohol Whereas enzymatic cascade reactions often benefit from a dehydrogenases are widely-used in cascade reactions, because similar reaction milieu, chemo-enzymatic combinations of their favourably biocatalyst stability, excellent encounter compatibility problems as either the biocatalyst is enantiodivergence and simple cofactor recycling methods. unstable in organic solvents or the organo- or metallo-catalyst One prominent example discussed here is a cascade for the is inactivated in aqueous environment.8 Several approaches amination of primary alcohols by Sattler et al. They combined a have been investigated like the stabilisation of enzymes or thermostable alcohol dehydrogenase (ADH-hT) from Bacillus chemo-catalyst9 via different protein engineering approaches, stearothermophilus with an ω-transaminase (ω-TA) from This journal is © The Royal Society of Chemistry 2013 Chem. Comm., 2014, 00, 1-3 | 2 Page 3 of 15 ChemComm Chem. Comm. Feature Article Chromobacterium violaceum and an L-alanine dehydrogenase protein engineering step or a different ADH would be necessary from Bacillus subtilis for recycling of the amine donor to complete the cascade as proposed by the authors. (Fig. 1A) in a strictly “non” buffered system.16 The authors The direct oxidation of cycloalkanes to cycloalkanones via a demonstrated a redox neutral multi-enzyme network by P450 monooxygenase and an ADH (Fig. 2A) represents another applying the proper cofactor recycling system. Hence, the successful enzyme cascade.18 Again, protein engineering of equilibrium of the cascade was shifted towards the product side suitable P450 monooxygenases identified the BM3 variants by addition of the cheap amine-donor ammonia. Finally, the 19A12 and F87V (originating from Bacillus megaterium BM3) authors renounced the use of buffers in their cascade reaction as the best candidates for cycloalkane hydroxylation. system to avoid any salt waste and make the process Combination of the ADH from Lactobacillus kefir and the BM3 environment friendly. mutants enabled production of cyclooctanone (6.3 mM) and With this system they reached nearly full conversion of 50 mM cyclohexanone (4.1 mM) starting from the corresponding 1-hexanol to 1-hexylamine and 3-phenyl-1-propanol to cycloalkane (100 mM). Although the sequence gave the desired 3-phenyl-1-propylamine. After the first successful proof of this products, the low activity of the P450 monooxygenase turned concept, the authors investigated the production of out as bottleneck of the cascade. Protein engineering of the 1,ω-diamines from 1,ω-diols (Fig. 1B). By optimizing the P450 monooxygenase with respect to activity, stability, and reaction conditions
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