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

作者：Zhu, Dunming^*; Ankati, Haribabu; Mukherjee, Chandrani; Yang, Yan; Biehl, Edward R.; Hua, Ling

来源：Organic Letters, 2007, 9(13): 2561-2563.

DOI：10.1021/ol070962b

• ENANTIOSELECTIVE SYNTHESIS
• TRANSFER HYDROGENATION
• NITRILES
• 3-HYDROXYALKANENITRILES
• HYDROLYSIS
• FLUOXETINE
• RESOLUTION
• ALCOHOLS

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.

• 出版日期2007-6-21