Practical Asymmetric Enzymatic Reduction through Discovery of a Dehydrogenase-Compatible Biphasic Reaction Media

Harald Gröger,* Werner Hummel,*§ Stefan Buchholz, Karlheinz Drauz, Tien Van Nguyen,§ Claudia Rollmann, Hendrik Hüsken, and Kofi Abokitse§
Degussa AG, Project House Biotechnology, P.O. Box 1345, 63403 Hanau, Germany, Institut fr Enzymtechnologie der Heinrich-Heine-Universitt, Forschungszentrum Jlich, Stetternicher Forst, 52426 Jlich, Germany, and Degussa AG, BU Fine Chemicals, FC-TRM, P.O. Box 1345, 63403 Hanau, Germany
Org. Lett., 2003, 5 (2), pp 173–176
DOI: 10.1021/ol0272139
Publication Date (Web): January 1, 2003
Copyright © 2003 American Chemical Society

 Dedicated to Professor Dr. Heribert Offermanns on the occasion of his 65th birthday.

,
*

 Corresponding authors. E-mail address for W.H.:  w.hummel@fz-juelich.de.

,

 Degussa AG, Project House Biotechnology.

,
§

 Heinrich-Heine-Universität.

,

 Degussa AG, BU Fine Chemicals.

, harald.groeger@degussa.com

Abstract

Abstract Image

An enzyme-compatible biphasic reaction media for the asymmetric biocatalytic reduction of ketones with in situ cofactor regeneration has been developed. In this biphasic reaction media, which is advantageous for reactions at higher substrate concentrations, both enzymes (alcohol dehydrogenase and FDH from Candida boidinii) remain stable. The reductions with poorly water-soluble ketones were carried out at substrate concentrations of 10−200 mM, and the optically active (S)-alcohols were formed with moderate to good conversions and with up to >99% ee.

Tools

History

  • Published In Issue January 23, 2003
  • Received October 31, 2002

Recommend & Share