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Identification of a Candida sp reductase behind bicyclic exo-alcohol production

Johanson, Ted LU ; Skorupa Parachin, Nadia LU ; Adamis, Paula LU and Gorwa-Grauslund, Marie-Francoise LU (2009) In Journal of Molecular Catalysis B: Enzymatic 59(4). p.286-291
Abstract
Stereoselective baker's yeast-catalysed bioreduction of bicyclo [2.2.2]octane-2.6-dione generates (1R, 4S, 6S)-6-hydroxy-bicyclo [2.2.2]octane-2-one (endo-alcohol) with high enantiomeric and diastereomeric excess. In contrast, whole cells and crude membrane fractions of Candida sp. have been reported to produce the unusual (I R, 4S, 6S)-diastereomer (exo-alcohol) as a major product. Previous in silica screening has identified seven membrane or membrane-bound reductases in C albicans as candidates for the exoactivity. In this work, purification of the corresponding exo-reductase(s) as well as the heterologous cloning of the seven candidate genes was attempted in C tropicalis. The overexpression of IPF4033 (AYR1) gene generated an increased... (More)
Stereoselective baker's yeast-catalysed bioreduction of bicyclo [2.2.2]octane-2.6-dione generates (1R, 4S, 6S)-6-hydroxy-bicyclo [2.2.2]octane-2-one (endo-alcohol) with high enantiomeric and diastereomeric excess. In contrast, whole cells and crude membrane fractions of Candida sp. have been reported to produce the unusual (I R, 4S, 6S)-diastereomer (exo-alcohol) as a major product. Previous in silica screening has identified seven membrane or membrane-bound reductases in C albicans as candidates for the exoactivity. In this work, purification of the corresponding exo-reductase(s) as well as the heterologous cloning of the seven candidate genes was attempted in C tropicalis. The overexpression of IPF4033 (AYR1) gene generated an increased exo-to-endo ratio and exo-alcohol production in whole cells and membranes of C tropicalis. In addition, a slight increased exo-to-endo ratio was observed when overexpressing IPF4033 in S. cerevisiae, although the reduction rate and exo-to-endo ratio were several fold lower compared to those obtained with C. tropicalis. (C) 2008 Elsevier B.V. All rights reserved. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Exo-alcohol, Candida albicans, Candida, tropicalis, Membrane reductase, AYR1, IPF4033, Bicyclic diketone, Bioreduction
in
Journal of Molecular Catalysis B: Enzymatic
volume
59
issue
4
pages
286 - 291
publisher
Elsevier
external identifiers
  • wos:000266616800011
  • scopus:67349175274
ISSN
1873-3158
DOI
10.1016/j.molcatb.2008.11.002
language
English
LU publication?
yes
id
09a539f1-2e75-4e88-9a61-9d42126af722 (old id 1443582)
date added to LUP
2009-07-24 12:45:54
date last changed
2017-01-01 04:49:54
@article{09a539f1-2e75-4e88-9a61-9d42126af722,
  abstract     = {Stereoselective baker's yeast-catalysed bioreduction of bicyclo [2.2.2]octane-2.6-dione generates (1R, 4S, 6S)-6-hydroxy-bicyclo [2.2.2]octane-2-one (endo-alcohol) with high enantiomeric and diastereomeric excess. In contrast, whole cells and crude membrane fractions of Candida sp. have been reported to produce the unusual (I R, 4S, 6S)-diastereomer (exo-alcohol) as a major product. Previous in silica screening has identified seven membrane or membrane-bound reductases in C albicans as candidates for the exoactivity. In this work, purification of the corresponding exo-reductase(s) as well as the heterologous cloning of the seven candidate genes was attempted in C tropicalis. The overexpression of IPF4033 (AYR1) gene generated an increased exo-to-endo ratio and exo-alcohol production in whole cells and membranes of C tropicalis. In addition, a slight increased exo-to-endo ratio was observed when overexpressing IPF4033 in S. cerevisiae, although the reduction rate and exo-to-endo ratio were several fold lower compared to those obtained with C. tropicalis. (C) 2008 Elsevier B.V. All rights reserved.},
  author       = {Johanson, Ted and Skorupa Parachin, Nadia and Adamis, Paula and Gorwa-Grauslund, Marie-Francoise},
  issn         = {1873-3158},
  keyword      = {Exo-alcohol,Candida albicans,Candida,tropicalis,Membrane reductase,AYR1,IPF4033,Bicyclic diketone,Bioreduction},
  language     = {eng},
  number       = {4},
  pages        = {286--291},
  publisher    = {Elsevier},
  series       = {Journal of Molecular Catalysis B: Enzymatic},
  title        = {Identification of a Candida sp reductase behind bicyclic exo-alcohol production},
  url          = {http://dx.doi.org/10.1016/j.molcatb.2008.11.002},
  volume       = {59},
  year         = {2009},
}