Skip to main content

Lund University Publications

LUND UNIVERSITY LIBRARIES

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)
Please use this url to cite or link to this publication:
author
; ; and
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
2016-04-01 12:05:44
date last changed
2022-04-21 02:25:44
@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}},
  keywords     = {{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}},
  doi          = {{10.1016/j.molcatb.2008.11.002}},
  volume       = {{59}},
  year         = {{2009}},
}