Issue 8, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

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

Adriana L. Botes,*a   Daniel Harvig,†ac   Martha S. van Dyk,a   Ian Sarvary,b   Torbjörn Frejd,*b   Mikael Katz,c   Bärbel Hahn-Hägerdalc  and  Marie F. Gorwa-Grauslund*c  

* Corresponding authors

a Department of Microbiology and Biochemistry, University of the Free State, P.O. Box 339, Bloemfontein 9300, South Africa
E-mail: botesal@sci.uovs.ac.za
Fax: + 2751 444 3219
Tel: + 2751 401 3231

b Department of Organic and Bioorganic Chemistry, Center for Chemistry and Chemical Engineering, Lund University, P.O. Box 124, S-221 00 Lund, Sweden
E-mail: torbjorn.frejd@orgk1.lu.se
Fax: + 4646 222 4119
Tel: + 4646 222 8125

c Department of Applied Microbiology, Center for Chemistry and Chemical Engineering, Lund University, P.O. Box 124, S-221 00 Lund, Sweden
E-mail: marie-francoise.gorwa@tmb.lth.se
Fax: + 4646 222 4203
Tel: + 4646 222 0619

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.

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

About
Cited by
Related
Download options Please wait...

Article information

DOI
https://doi.org/10.1039/B111064K
Article type
Paper
Submitted
04 Dec 2001
Accepted
06 Mar 2002
First published
20 Mar 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 1111-1114

Permissions

Request permissions

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

A. L. Botes, D. Harvig, M. S. van Dyk, I. Sarvary, T. Frejd, M. Katz, B. Hahn-Hägerdal and M. F. Gorwa-Grauslund, J. Chem. Soc., Perkin Trans. 1, 2002, 1111 DOI: 10.1039/B111064K

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements