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

Summary, in English

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.

• Author: AL Botes; D Harvig; MS van Dyk; Ian Sarvary; Torbjörn Frejd; M Katz; B Hahn-Hagerdal; Marie-Francoise Gorwa-Grauslund
• Department/s: Centre for Analysis and Synthesis; Applied Microbiology
• Publishing year: 2002
• Language: English
• Pages: 1111-1114
• Publication/Series: Journal of the Chemical Society - Perkin Transactions 1
• Issue: 8
• Links: http://dx.doi.org/10.1039/b111064k
• Document type: Journal article
• Publisher: Royal Society of Chemistry
• Topic: Organic Chemistry; Industrial Biotechnology
• Status: Published
• ISBN/ISSN/Other: ISSN: 1472-7781