AIMMS Seminar: Prof. Ulf Hanefeld

09/21/2017

16.00 - 17.00h

Auditorium, O|2 Lab Building

AIMMS Seminar: Biocatalytic routes to α-hydoxyketones

Prof. Ulf Hanefeld (Biocatalysis & Biotechnology Kluyver Lab, TUD)

Amsterdam Institute for Molecules, Medicines and Systems

Sciences

Seminar

Prof. Ulf Hanefeld (Biocatalysis & Biotechnology Kluyver Lab, TUD) will provide an AIMMS Seminar on 21 September entitled 'Biocatalytic routes to α-hydoxyketones'.

You are all cordially invited!

Abstract

α-Hydroxy ketones and vic-diols constitute well-known building blocks in organic synthesis. While excellent approaches towards the chiral diols exist the synthesis of α-hydroxy ketones still is a major challenge (Scheme 1).[1]

Based on dynamic kinetic resolutions (DKR) with heterogeneous acid and lipases the target compound could be obtained in good yields.[2] However, a recently described  enzyme, 2,3-butanediol dehydrogenase (BudC) from S. marcescens CECT 977, enables the enantioselective synthesis of α-hydroxy ketones starting from diketones or from vic-diols. BudC belongs to the NADH-dependent metal-independent short-chain dehydrogenases/reductases family (SDR) and catalyses the selective asymmetric reduction of prochiral diketones S-selectively.[3] Transketolase on the other hand has the advantage that it creates the new stereocentre in a C-C bond forming reaction, allowing much more flexibility in the planning of the synthesis. Here new developments on how to address the equilibrium of the reaction will be discussed.[4] The results of all approaches will be critically compared.

Figure_Ulf_Hanefeld

Scheme 1: Different biocatalytic routes to chiral α-hydroxyketones

Prof. Ulf Hanefeld

Prof. Ulf Hanefeld was born in Köln, Germany, and grew up in then (West) Berlin and London. In 1993 he received his PhD from the Georg-August-Universität zu Göttingen, having performed the research both with Prof. H. Laatsch (Göttingen) and Prof. H. G. Floss (Seattle). After postdoctoral years with Prof. C. W. Rees (Imperial College London), Prof. J. Staunton (Cambridge) and Prof.  J. J. Heijnen and Dr. A. J. J. Straathof (TU Delft), he received a fellowship from the Royal Netherlands Academy of Arts and Sciences (KNAW). He rose through the ranks at the Technische Universiteit Delft and his research in Delft focuses on enzymes, in particular HNLs, their immobilisation and application in organic synthesis.

Literature

[1] C. Palomo, M. Oiarbide, J. M. Garcia, Chem. Soc.Rev.2012, 41, 4150.

[2] R. Nieguth, J. ten Dam, A. Petrenz, A. Ramanathan, U. Hanefeld, M. B. Ansorge-Schumacher, RSC Adv., 2014, 4, 45495.

[3] R. Médici, H. Stammes, S. Kwakernaak, L. G. Otten, U. Hanefeld, Catal.Sci. Technol. DOI: 10.1039/c7cy00169j.

[4] S. R. Marsden, L. Gjonaj, S. J. Eustace, U. Hanefeld, ChemCatChem, DOI: 10.1002/cctc.201601649.