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

doi:10.1039/b111064k

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

Centre for Analysis and Synthesis

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	1111-1114
Journal	Journal of the Chemical Society - Perkin Transactions 1
Issue number	8
DOIs	https://doi.org/10.1039/b111064k
Publication status	Published - 2002

Bibliographical note

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)

Subject classification (UKÄ)

Organic Chemistry
Industrial Biotechnology

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10.1039/b111064k

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@article{daaa9dea2ac542b7b8e27ee91c86165b,

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

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.",

author = "AL Botes and D Harvig and \{van Dyk\}, MS and Ian Sarvary and Torbj{\"o}rn Frejd and M Katz and B Hahn-Hagerdal and Marie-Francoise Gorwa-Grauslund",

note = "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)",

year = "2002",

doi = "10.1039/b111064k",

language = "English",

pages = "1111--1114",

journal = "Journal of the Chemical Society - Perkin Transactions 1",

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T1 - Screening of yeast species for the stereo-selective reduction of bicyclo[2.2.2]octane-2,6-dione

AU - Botes, AL

AU - Harvig, D

AU - van Dyk, MS

AU - Sarvary, Ian

AU - Frejd, Torbjörn

AU - Katz, M

AU - Hahn-Hagerdal, B

AU - Gorwa-Grauslund, Marie-Francoise

N1 - 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)

PY - 2002

Y1 - 2002

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/0036010005

U2 - 10.1039/b111064k

DO - 10.1039/b111064k

M3 - Article

SN - 1472-7781

SP - 1111

EP - 1114

JO - Journal of the Chemical Society - Perkin Transactions 1

JF - Journal of the Chemical Society - Perkin Transactions 1

IS - 8

ER -

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

Abstract

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