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.

Harvig, D (author)
van Dyk, MS (author)
Sarvary, IanLund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH(Swepub:lu)orgk1-is (author)
Frejd, TorbjörnLund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH(Swepub:lu)orgk1-tf (author)
Katz, M (author)
Hahn-Hagerdal, B (author)
Gorwa-Grauslund, Marie-FrancoiseLund University,Lunds universitet,Teknisk mikrobiologi,Centrum för tillämpade biovetenskaper,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Applied Microbiology,Center for Applied Life Sciences,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH(Swepub:lu)tmb-mfg (author)
Centrum för analys och syntesKemiska institutionen (creator_code:org_t)

In:Journal of the Chemical Society - Perkin Transactions 1: Royal Society of Chemistry (RSC):8, s. 1111-11141472-77811364-5463

By the author/editor: Botes, AL; Harvig, D; van Dyk, MS; Sarvary, Ian; Frejd, Torbjörn; Katz, M; show more...; Hahn-Hagerdal, B; Gorwa-Grauslund, ...; show less...

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NATURAL SCIENCES: NATURAL SCIENCES; and Chemical Science ...; and Organic Chemistr ...

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