Screening of yeast species for the stereo-selective reduction of bicyclo[2.2.2]octane-2,6-dione
- 20 March 2002
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 8,p. 1111-1114
- https://doi.org/10.1039/b111064k
Abstract
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.Keywords
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