双环[2.2.2]辛烷-2,6-二酮立体选择性还原酵母菌的筛选

Journal of the Chemical Society, Perkin Transactions 2 Pub Date : 2002-04-09 DOI:10.1039/B111064K

A. L. Botes, Daniel Harvig, M. S. V. Dyk, I. Sarvary, T. Frejd, M. Katz, B. Hahn‐hägerdal, M. Gorwa-Grauslund

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引用次数: 15

摘要

从31个不同属的酵母菌株中筛选了对双环[2.2.2]辛烷-2,6-二酮的还原活性(1)。筛选的酵母菌中有80%具有还原活性。69%的菌株对映选择性地将双环[2.2.2]辛烷-2,6-二酮还原为(1R,4S,6S)-6-羟基双环[2.2.2]辛烷-2- 1(−)-2。本文首次报道了二酮对映选择性还原为(1S,4R,6S)-6-羟基双环[2.2.2]辛烷-2- 1 ((+)-3,bb0 98% ee)作为主要产物。热带假丝酵母UOFS Y-0534和维克哈密假丝酵母UOFS Y-0652表现出这种不寻常的非对异选择性。

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Screening of yeast species for the stereo-selective reduction of bicyclo[2.2.2]octane-2,6-dione

Yeast strains from more than 31 different genera were screened for the enantioselective reduction of bicyclo[2.2.2]octane-2,6-dione (1). Reducing activity was found in 80% of the screened yeasts. Bicyclo[2.2.2]octane-2,6-dione was enantioselectively reduced (>98% ee) to (1R,4S,6S)-6-hydroxybicyclo[2.2.2]octane-2-one (−)-2 by 69% of the strains. Enantioselective reduction of the diketone to (1S,4R,6S)-6-hydroxybicyclo[2.2.2]octane-2-one ((+)-3, >98% ee) as a major product is reported for the first time. Candida tropicalis UOFS Y-0534 and Candida wickerhamii UOFS Y-0652 displayed this unusual diastereoselectivity.

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Journal of the Chemical Society, Perkin Transactions 2

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