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The 43Rd EUCHEM Conference on Stereochemistry CONFERENCE REPORT 525 doi:10.2533/chimia.2008.525 CHIMIA 2008, 62, No. 6 CONFERENCE REPORT Chimia 62 (2008) 525–528 © Schweizerische Chemische Gesellschaft ISSN 0009–4293 The 43rd EUCHEM Conference on Stereo- chemistry (Bürgenstock Conference 2008) Fürigen, April 12–18, 2008 Hermann Wegner*a and Andreas Zumbuehl*b In an ever changing, metastable world of Don Hilvert (ETH Zürich) presided helped to shape generations of chemists, science and technology it is good to know over the symposium which attracted scien- planting the seed of curiosity deep within of facts that will never change. For decades tists from 22 countries. We all were curi- them together with an indestructible confi- now, the Bürgenstock Conference in spring ous what line-up of speakers the president dence in the power of organic synthesis. has been such an anchor-point, a week to had prepared together with vice-president step back and have a look at chemistry in Ben L. Feringa (University of Groningen) its pure and applied forms. A week to be and his organizing committee: François amongst people that speak the same lan- Diederich (ETH Zürich), E. Peter Kündig guage, a week to refocus one’s view of cur- (University of Geneva), Klaus Müller (F. rent science. Hoffmann-La Roche, Basel), Philippe Re- This year’s Bürgenstock conference naud (University of Berne), and Jay Siegel has passed already, leaving the participants (University of Zürich). The dinner on Sat- with the slightly melancholic impression of urday evening was thus left with satisfied having been a part of an important event in people looking forward to an exceptional chemistry. week to come. Dieter Seebach On an easy early spring Sunday morn- ing – at nine o’clock sharp − Prof. Schwarz opened with Swiss ‘Pünktlichkeit’ the sci- entific part of the 43. Bürgenstock confer- ence. The honor of the first lecture was given to Jérôme Lacour (University of Ge- neva), who set the standard for this meeting a b * Correspondence: Dr. H. Wegner , Dr. A. Zumbuehl Don Hilvert a Department of Organic Chemistry with a fulminant talk about chiral ions in University of Basel asymmetric synthesis. He developed with St. Johanns-Ring 19 his coworkers helical chiral phosphonate CH-4056 Basel The first pleasant surprise was meeting anions. As counter ion with metal salts they E-Mail: [email protected] b Department of Organic Chemistry this year’s guest of honour, Dieter Seebach create a chiral environment, which Jérôme University of Geneva (ETH Zürich) one of the corner stones of demonstrated in thoroughly designed NMR 30, quai E. Ansermet current synthetic chemistry. Through his experiments. Application of his TRISPHAT CH-1211 Genève 4 E-Mail: [email protected] impressive list of contributions, he has counterion in the first asymmetric 1,2-Ste- CONFERENCE REPORT 526 CHIMIA 2008, 62, No. 6 vens rearrangement proved that this is using acetaldehyde in enamine catalysis. cinogenicity and the need for an additional not just an exercise of theoretical intent. In the last part of his talk, Ben presented proofreading mechanism in humans by e.g. Additionally, he designed a highly selec- his new concept of asymmetric counterion MutSα . With the latter, Lorena crossed the tive catalyst for an asymmetric Carroll- directed catalysis (ACDC), which will not bridge to human systems, opening new rearrangement, based on a RuCp-complex only ‘rock’ the organocatalytic community. fields in cancer therapy. in combination with chiral Schiff base li- He showcased the concept in, for example, gands. An interesting observation on the an asymmetric epoxidation. aging of the catalytic species led Jérôme to discover new air stable catalysts that were As spectacular as the first day started it end- easily separable by column chromatogra- ed with a blooming presentation by Roman phy on silica gel. Kaiser (Givaudan) capturing the ‘Scents of the Vanishing Flora’. For over 30 years, as stated by the moderator Lia Addadi, he has been tracking down the bouquet of Earth’s remotest places. His latest project hunts down the odors of endangered plants, col- lecting samples of over 2500 species. In his lecture, he took an awed audience on a trip around the world of olfactory experiences, illustrated by distributed perfumers testing strips. We learned about Dracula chester- tonii (that not only mimics the shape of a fungus, but also its smell), or the desert gold Lorena S. Beese plant from Death Valley that produces chlo- rinated phenols originating from the soil’s high salt concentration. The complexity Moving from DNA to peptide synthesis, of smelling was demonstrated by a scent Mohamed A. Marahiel (Philipps Universi- sample of a Sauvignon Blanc Palliser Es- ty Marburg) presented his latest results on Jérôme Lacour tate 2000, an ultimate challenge for anyone non-ribosomal peptide synthesis (NRPS). working in the field. Compared to the classical ribosomal pep- tide synthesis, the NRPS is able to intro- Equally young and enthusiastic, Ben- duce a larger variety of over 450 different jamin List (MPI Mühlheim) presented his building blocks, allowing much higher lecture about new strategies and concepts complexities. Molecules like bleomycin, for catalysis. Without doubt he is one of the surfactin, cyclosporin and vancomycin are defining characters in the rejuvenated field just a few examples of the synthetic power of organocatalysis. In only a few years, he of NRPS. In order to possibly exploit this and his young group have developed asym- natural assembly line for organic synthesis, metric catalytic versions of a variety of clas- a deep understanding of its architecture and sic reactions, like aldol, Mannich, Michael, function is needed. Mohamed impressively etc. In the case of aldol condensations, he elucidated the modular structure of the sur- distinguished four modes of action: Inter- factin biosynthesis cluster from crystals molecular, intramolecular endo− endo and and NMR studies. From these results he endo− exo and finally transannular. For the was able to predict and modify the protein latter he recently published an organocata- structure in order to incorporate specific lytic asymmetric version, which he fea- amino acids during the peptide synthesis. tured in the shortest asymmetric synthesis Mohamed ended his talk with his inspir- of (+)-hirsutene. He also solved one of the Roman Kaiser ing vision of the architecture of a complete longstanding problems in organocatalysis nonribosomal assembly line. With Don Hilvert as this year’s presi- dent, the conference promised to also high- light recent advances in biology. Indeed, Ilme Schlichting chaired the Monday morn- ing session on life’s molecular machines. Lorena S. Beese (Duke University Medi- cal Center) investigated the high-fidelity of DNA synthesis by analyzing an impressive number of crystal structures. Using a co- crystallization technique she was able to snapshot different stages of action of DNA polymerase I and the effect of the various nucleotide mismatches. Lorena further showed crystal structures with incorporated modified nucleosides (O6MeG and 8oxoG), noting the perfect fit into the natural DNA Benjamin List double helix, which explains their high car- Mohamed A. Marahiel CONFERENCE REPORT 527 CHIMIA 2008, 62, No. 6 The title of the evening promised a es a C 2 -symmetric α -diimine Ni-catalyst to The fourth science day of the meeting, sweet lecture. After an introduction by Pe- induce a living polymerization of propylene moderated by Beate Koksch , was again ter Seeberger , Ben Davis (University of to form thermoplastic elastomers. A project under the stars of biochemistry. The first Oxford) started a firework on sugar and dear to Geoffrey’s heart is the development lecture by Frances H. Arnold (California protein chemistry. Glycosylation is one of of biodegradable and environmental friend- Institute of Technology) dealt with her ‘fa- the most important posttranslational modi- ly polymers based on CO2 monomers. He vored chemist’, Nature’s cytochrom P450 fications used by Nature to decorate pro- showed that Zn- and Co catalysts can form heme-mono oxygenase. Probing into the teins. Mimicking this process in the chemi- poly(propylene)carbonates. In the course of vast sequence space she was able to decou- cal laboratory will allow protein functions his research on poly(β -hydroxybutyrates) ple the enzyme from its biological context. to be finetuned. Ben’s first approach relied he discovered an intriguing insertion reac- She changed the function of cytochrom on a mixed sulfur-selenium reagent strategy tion of CO into cyclic ethers to form lac- P450 BM3 from subterminal oxidation of to site-selectively couple sugars to proteins. tones. fatty acids to the oxidation of propane using He then went on to more complex systems, directed evolution, a technique pioneered ultimately using PSGL-lacZ as an inflam- After this splendid start Kyoko Nozaki in her laboratory. She experienced the fine mation marker in a rat cortex. MRI active (University of Tokyo) stepped into her fa- line between optimizing turnover numbers GNPs allow e.g. the visualization of inflam- ther’s footsteps, who gave a lecture at the and stability of the protein. The knowledge mation in an in vivo stroke model. In order 15. Bürgenstock Conference in 1979. She obtained in that process was applied to the to selectively decorate proteins with differ- presented her work on olefin− CO co-po- oxidation of other alkanes by enzymes, as ent sugars, he developed new orthogonal lymerization catalyzed by Pd(II)-(R , S )-BI- well as the selective deprotection of per- strategies, such as methods to form sulfide NAPHOS. By carefully combining experi- methylated sugars. A now commercially bridges, cross-metathesis and click chem- mental and theoretical data she elucidated available plate with 120 mutants of P450 istry. the stepwise chain propagation mechanism. was used in her laboratory to create milli- A thorough analysis of the 3D structure of gram quantities of dozens of metabolites of these polymers revealed an equilibrium be- drug candidates in one week.
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