A. L. Botes, Daniel Harvig, M. S. V. Dyk, I. Sarvary, T. Frejd, M. Katz, B. Hahn‐hägerdal, M. Gorwa-Grauslund
{"title":"Screening of yeast species for the stereo-selective reduction of bicyclo[2.2.2]octane-2,6-dione","authors":"A. L. Botes, Daniel Harvig, M. S. V. Dyk, I. Sarvary, T. Frejd, M. Katz, B. Hahn‐hägerdal, M. Gorwa-Grauslund","doi":"10.1039/B111064K","DOIUrl":null,"url":null,"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.","PeriodicalId":17260,"journal":{"name":"Journal of the Chemical Society, Perkin Transactions 2","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2002-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"15","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the Chemical Society, Perkin Transactions 2","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1039/B111064K","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 15
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.
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