Biocatalytic Asymmetric Hydrogen Transfer Employing Rhodococcus ruber DSM 44541

Wolfgang Stampfer, Birgit Kosjek, Kurt Faber, and Wolfgang Kroutil*
Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria
J. Org. Chem., 2003, 68 (2), pp 402–406
DOI: 10.1021/jo026216w
Publication Date (Web): December 5, 2002
Copyright © 2003 American Chemical Society
*

 To whom correspondence should be addressed. Tel:  +43-316-380-5350. Fax:  +43-316-380-9840.

, Wolfgang.Kroutil@uni-graz.at

Abstract

Abstract Image

Nonracemic sec-alcohols of opposite absolute configuration were obtained either by asymmetric reduction of the corresponding ketone using 2-propanol as hydrogen donor or by enantioselective oxidation through kinetic resolution of the rac-alcohol using acetone as hydrogen acceptor employing whole lyophilized cells of Rhodococcus ruber DSM 44541. The microbial oxidation/reduction system exhibits not only excellent stereo- and enantioselectivity but also a broad substrate spectrum. Due to the exceptional tolerance of the biocatalyst toward elevated concentrations of organic materials (solvents, substrates and cosubstrates), the process is highly efficient. The simple preparation of the biocatalyst and its ease of handling turns this system into a versatile tool for organic synthesis.

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History

  • Published In Issue January 24, 2003
  • Received July 19, 2002

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