Stereochemical Control in Microbial Reduction. 18. Mechanism of Stereochemical Control in the Diastereoselective Reduction with Bakers' Yeast.
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概要
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Reduction of a variety of 2-alkyl-3-oxobutanoates with bakers' yeast yields the corresponding L-(3<I>S</I>)-hydroxy esters with exclusive enantioselectivity, while the diastereoselectivity, syn/anti ratio, varies depending on the structure of the alkoxyl moiety. In order to elucidate the mechanism for this stereochemical control, oxidoreductases that reduce 2-alkyl-3-oxobutanoate have been isolated from the cells of bakers' yeast and purified. Two dominant competing 2-alkyl-3-hydroxybutanoate oxidoreductases have been obtained: one of them reduces 2-alkyl-3-oxobutanoates stereoselectively yielding the corresponding L-<I>syn</I>-hydroxy esters, whereas the other affords a mixture of L-<I>syn</I>- and L-<I>anti</I>-hydroxy esters. The experimental results on stereoselectivity have nicely been simulated using kinetic parameters elucidated.
- 公益社団法人 日本化学会の論文
著者
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Kawai Yasushi
Institute For Chemical Research Kyoto University
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Ohno Atsuyoshi
Institute For Chemical Research Kyoto Univ.
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Nakamura Kaoru
Institute For Chemical Research Kyoto University
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Miyai Takehiko
Institute For Chemical Research Kyoto University
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Nakajima Nobuyoshi
Department of Food and Nutrition, Okayama Prefectural Junior College
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Honda Sohichi
Institute for Chemical Research, Kyoto University
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