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

AL Botes, D Harvig, MS van Dyk, Ian Sarvary, Torbjörn Frejd, M Katz, B Hahn-Hagerdal, Marie-Francoise Gorwa-Grauslund

Forskningsoutput: TidskriftsbidragArtikel i vetenskaplig tidskriftPeer review

Sammanfattning

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.
Originalspråkengelska
Sidor (från-till)1111-1114
TidskriftJournal of the Chemical Society - Perkin Transactions 1
Nummer8
DOI
StatusPublished - 2002

Bibliografisk information

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240), Applied Microbiology (LTH) (011001021)

Ämnesklassifikation (UKÄ)

  • Organisk kemi
  • Industriell bioteknik

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