Asymmetric reduction of beta-ketonitriles with a recombinant carbonyl reductase and enzymatic transformation to optically pure beta-hydroxy carboxylic acids

Org Lett. 2007 Jun 21;9(13):2561-3. doi: 10.1021/ol070962b. Epub 2007 May 24.

Abstract

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

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alcohol Oxidoreductases / metabolism*
  • Carboxylic Acids / metabolism*
  • Molecular Structure
  • NADP / metabolism
  • Nitriles / metabolism*

Substances

  • Carboxylic Acids
  • Nitriles
  • NADP
  • Alcohol Oxidoreductases