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

Botes, AL ; Harvig, D ; van Dyk, MS ; Sarvary, Ian LU ; Frejd, Torbjörn LU ; Katz, M ; Hahn-Hagerdal, B and Gorwa-Grauslund, Marie-Francoise LU (2002) In Perkin Transactions 1 p.1111-1114
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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organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Perkin Transactions 1
issue
8
pages
1111 - 1114
publisher
Royal Society of Chemistry
external identifiers
  • wos:000175001100014
  • scopus:0036010005
ISSN
1472-7781
DOI
10.1039/b111064k
language
English
LU publication?
yes
additional info
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)
id
daaa9dea-2ac5-42b7-b8e2-7ee91c86165b (old id 340240)
date added to LUP
2016-04-01 15:16:56
date last changed
2020-01-12 18:19:16
@article{daaa9dea-2ac5-42b7-b8e2-7ee91c86165b,
  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       = {Botes, AL and Harvig, D and van Dyk, MS and Sarvary, Ian and Frejd, Torbjörn and Katz, M and Hahn-Hagerdal, B and Gorwa-Grauslund, Marie-Francoise},
  issn         = {1472-7781},
  language     = {eng},
  number       = {8},
  pages        = {1111--1114},
  publisher    = {Royal Society of Chemistry},
  series       = {Perkin Transactions 1},
  title        = {Screening of yeast species for the stereo-selective reduction of bicyclo[2.2.2]octane-2,6-dione},
  url          = {http://dx.doi.org/10.1039/b111064k},
  doi          = {10.1039/b111064k},
  year         = {2002},
}