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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, Email: lhuasmu.edu

D. Zhu, H. Ankati, C. Mukherjee, Y. Yang, E. R. Biehl, L. Hua, Org. Lett., 2007, 9, 2561-2563.

DOI: 10.1021/ol070962b (free Supporting Information)


Abstract

(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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Key Words

Reduction, Hydrolysis, β-Cyanohydrins


ID: J54-Y2007-2020