Identification of a Candida sp reductase behind bicyclic exo-alcohol production
(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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https://lup.lub.lu.se/record/1443582
- author
- Johanson, Ted LU ; Skorupa Parachin, Nadia LU ; Adamis, Paula LU and Gorwa-Grauslund, Marie-Francoise LU
- organization
- publishing date
- 2009
- 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}}, }