Asymmetric Reduction of β-Ketonitriles with a Recombinant Carbonyl Reductase and Enzymatic Transformation to Optically Pure β-Hydroxy Carboxylic Acids

Dunming Zhu, Haribabu Ankati, Chandrani Mukherjee, Yan Yang, Edward R. Biehl, and Ling Hua*
Department of Chemistry, Southern Methodist University, Dallas, Texas 75275
Org. Lett., 2007, 9 (13), pp 2561–2563
DOI: 10.1021/ol070962b
Publication Date (Web): May 24, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, lhua@smu.edu

Abstract

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α-Ethylation is concomitant with the reduction of aromatic β-ketonitriles catalyzed by whole-cell biocatalysts. Use of isolated carbonyl reductase has completely eliminated this competing reaction. (R)-β-Hydroxy nitriles were obtained via a reduction catalyzed by a recombinant carbonyl reductase with excellent optical purity and were further converted to (R)-β-hydroxy carboxylic acids via a nitrilase-catalyzed hydrolysis. The present study allows ready access to both chiral β-hydroxy nitriles and β-hydroxy carboxylic acids of pharmaceutical importance.

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  • Published In Issue June 21, 2007
  • Received April 24, 2007

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