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Transaminases are still one of the major research areas of our group, and apart from kinetic resolution, asymmetric synthesis and deracemisation they have recently also been applied for racemisation of α-chiral primary amines:
In the field of "green" oxidation chemistry we have two new articles to offer: Mutti et al. found that alkene cleavage by peroxidases is also catalysed by heme groups; the authors have coined the term "ostensible enzyme promiscuity" to describe phenomena of this kind. Schittmayer et al. have virtually gathered all the biocatalytic competence Graz has to offer (and additional co-workers from abroad) for their investigation of the aerobic dehydrogenation of ketones by Geobacillus kaustophilus OYE.
- Ostensible Enzyme Promiscuity: Alkene Cleavage by Peroxidases
F. G. Mutti, M. Lara, M. Kroutil, W. Kroutil, Chem.-Eur. J. 2010, 16, 14142–14148.
- Old Yellow Enzyme-Catalyzed Dehydrogenation of Saturated Ketones
M. Schittmayer, A. Glieder, M. K. Uhl, A. Winkler, S. Zach, J. H. Schrittwieser, W. Kroutil, P. Macheroux, K. Gruber, S. Kambourakis, J. D. Rozzell, M. Winkler, Adv. Synth. Catal. 2011, 353, 268–274.
The integration of several biocatalytic steps and the combination of enzymatic and chemical transformations is a further "hot topic" in our research group: Recently we have reported the combination of Ir-catalysed oxidation and ADH-catalysed reduction in one pot. In addition, a review on oxidation/reduction cascades is currently in press.
- Simultaneous iridium catalysed oxidation and enzymatic reduction employing orthogonal reagents
F. G. Mutti, A. Orthaber, J. H. Schrittwieser, J. G. de Vries, R. Pietschnig, W. Kroutil, Chem. Commun. 2010, 16, 8046–8048.
- Recent biocatalytic oxidation–reduction cascades
J. H. Schrittwieser, J. H. Sattler, V. Resch, F. G. Mutti, W. Kroutil, Curr. Opin. Chem. Biol. 2011, in press
Our recent efforts to expand the toolbox for biocatalytic C–C bond formation has led to the development of a novel oxidative kinetic resolution of benzylisoquinoline alkaloids, allowing us to synthesise several novel compounds in enantiomerically pure form. This work was considered a "very important paper" by Angewandte Chemie and made it to the cover of its issue. A review article highlighting several novel C–C bond forming enzymes is currently in press.
- Biocatalytic Enantioselective Oxidative C–C Coupling by Aerobic C–H Activation
J. H. Schrittwieser, V. Resch, J. H. Sattler, W.-D. Lienhart, K. Durchschein, A. Winkler, K. Gruber, P. Macheroux, W. Kroutil, Angew. Chem. Int. Ed. 2011, 50, 1068–1071.
- Novel carbon–carbon bond formations for biocatalysis
V. Resch, J. H. Schrittwieser, E. Siirola, W. Kroutil, Curr. Opin. Biotechnol. 2011, in press
Our enoate-reductase subgroup has also been very productive in the last months, as indicated by three new publications: The asymmetric synthesis of aroma compounds, the famous "Roche ester" and O-protected acyloins has been reported.
- Bioreduction of α-methylcinnamaldehyde derivatives: chemo-enzymatic asymmetric synthesis of LilialTM and HelionalTM
C. Stueckler, N. J. Mueller, C. K. Winkler, S. M. Glueck, K. Gruber, G. Steinkellner, K. Faber, Dalton Trans. 2010, 39, 8472–8476.
- Asymmetric synthesis of (R)-3-hydroxy-2-methylpropanoate ("Roche Ester") and derivatives via biocatalytic C=C-bond reduction
C. Stueckler, C. K. Winkler, M. Bonnekessel, K. Faber, Adv. Synth. Catal. 2010, 352, 2663–2666.
- Asymmetric Synthesis of O-Protected Acyloins Using Enoate Reductases: Stereochemical Control through Protecting Group Modification
C. K. Winkler, C. Stueckler, N. J. Mueller, D. Pressnitz, K. Faber, Eur. J. Org. Chem. 2010, 6354–6358.
joerg mar2011
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