Asymmetric Reduction of α-Keto Esters and α-Diketones with a Bakers’ Yeast Keto Ester Reductase

Asymmetric Reduction of α-Keto Esters and α-Diketones with a Bakers’ Yeast Keto Ester Reductase

Optically pure α-hydroxy esters and α-hydroxy ketones have been synthesized by the reduction of the corresponding ketones with a keto ester reductase isolated from bakers’ yeast (YKER-I). The reduction of α-keto esters affords the corresponding (S)- or (R)-hydroxy esters selectively, where the stere...

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Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan Vol. 72; no. 1; pp. 99 - 102
Main Authors: Kawai, Yasushi, Hida, Kouichi, Tsujimoto, Munekazu, Kondo, Shin-ichi, Kitano, Kazutada, Nakamura, Kaoru, Ohno, Atsuyoshi
Format: Journal Article
Language:English
Published: The Chemical Society of Japan 01-01-1999
Online Access:Get full text
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Summary:Optically pure α-hydroxy esters and α-hydroxy ketones have been synthesized by the reduction of the corresponding ketones with a keto ester reductase isolated from bakers’ yeast (YKER-I). The reduction of α-keto esters affords the corresponding (S)- or (R)-hydroxy esters selectively, where the stereochemical course depends on the chain length of the alkyl substituent on the carbonyl group. An α-keto short alkanoic ester affords the corresponding (S)-hydroxy ester, whereas a long alkanoate yields the corresponding (R)-hydroxy ester. The reduction of α-diketones affords the corresponding (S)-2-hydroxy ketones regio- and stereoselectively.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.72.99