Kinetic resolution of racemic 5,6-epoxy-bicyclo[2.2.1]heptane-2-one using genetically engineered Saccharomyces cerevisiae
(2009) In Journal of Molecular Catalysis B: Enzymatic 58(2). p.98-102- Abstract
- (+)-5,6-Epoxy-bicyclo[2.2.1]heptane-2-one, (+)-1, and endo-(−)-5,6-epoxy-bicyclo[2.2.1]heptane-2-ol,
endo-(−)-2, were obtained by kinetic resolution of rac-1 by asymmetric bioreduction catalyzed by whole
cells of a genetically engineered Saccharomyces cerevisiae yeast strain. The strain, TMB4100, had 1% phosphoglucose
isomerase (PGI) activity and overexpressed a specific short-chain dehydrogenase, encoded
by the gene YMR226c. The whole cell biocatalystwas demonstrated to be significantly inactivated within
24 h, thus restricting the reaction to lowconcentration. Despite this, the resolution method could be used
to produce optically pure (+)-1 and endo-(−)-2 from the racemic mixture at 5... (More) - (+)-5,6-Epoxy-bicyclo[2.2.1]heptane-2-one, (+)-1, and endo-(−)-5,6-epoxy-bicyclo[2.2.1]heptane-2-ol,
endo-(−)-2, were obtained by kinetic resolution of rac-1 by asymmetric bioreduction catalyzed by whole
cells of a genetically engineered Saccharomyces cerevisiae yeast strain. The strain, TMB4100, had 1% phosphoglucose
isomerase (PGI) activity and overexpressed a specific short-chain dehydrogenase, encoded
by the gene YMR226c. The whole cell biocatalystwas demonstrated to be significantly inactivated within
24 h, thus restricting the reaction to lowconcentration. Despite this, the resolution method could be used
to produce optically pure (+)-1 and endo-(−)-2 from the racemic mixture at 5 g/L substrate. At optimal
conditions, 1 g of rac-1 was kinetically resolved to give (+)-1 in 95% ee and 28% yield and endo-(−)-2 in
74% ee, 80% de and 45% yield. (Less)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/1393850
- author
- Carlquist, Magnus LU ; Olsson, Cecilia LU ; Bergdahl, Basti LU ; van Niel, Ed LU ; Gorwa-Grauslund, Marie-Francoise LU and Frejd, Torbjörn LU
- organization
- publishing date
- 2009
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- Baker's yeast, Saccharomyces cerevisiae, epoxide, racemic epoxy ketone, bioreduction, asymmetric carbonyl reduction, kinetic resolution, enantiomeric ratio, kinetic model
- in
- Journal of Molecular Catalysis B: Enzymatic
- volume
- 58
- issue
- 2
- pages
- 98 - 102
- publisher
- Elsevier
- external identifiers
-
- wos:000265584200016
- scopus:63249094069
- ISSN
- 1873-3158
- DOI
- 10.1016/j.molcatb.2008.11.014
- 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
- 36655255-b4d0-4dc4-909f-121e3fea6465 (old id 1393850)
- date added to LUP
- 2016-04-04 10:18:57
- date last changed
- 2022-01-29 20:04:34
@article{36655255-b4d0-4dc4-909f-121e3fea6465, abstract = {{(+)-5,6-Epoxy-bicyclo[2.2.1]heptane-2-one, (+)-1, and endo-(−)-5,6-epoxy-bicyclo[2.2.1]heptane-2-ol,<br/><br> endo-(−)-2, were obtained by kinetic resolution of rac-1 by asymmetric bioreduction catalyzed by whole<br/><br> cells of a genetically engineered Saccharomyces cerevisiae yeast strain. The strain, TMB4100, had 1% phosphoglucose<br/><br> isomerase (PGI) activity and overexpressed a specific short-chain dehydrogenase, encoded<br/><br> by the gene YMR226c. The whole cell biocatalystwas demonstrated to be significantly inactivated within<br/><br> 24 h, thus restricting the reaction to lowconcentration. Despite this, the resolution method could be used<br/><br> to produce optically pure (+)-1 and endo-(−)-2 from the racemic mixture at 5 g/L substrate. At optimal<br/><br> conditions, 1 g of rac-1 was kinetically resolved to give (+)-1 in 95% ee and 28% yield and endo-(−)-2 in<br/><br> 74% ee, 80% de and 45% yield.}}, author = {{Carlquist, Magnus and Olsson, Cecilia and Bergdahl, Basti and van Niel, Ed and Gorwa-Grauslund, Marie-Francoise and Frejd, Torbjörn}}, issn = {{1873-3158}}, keywords = {{Baker's yeast; Saccharomyces cerevisiae; epoxide; racemic epoxy ketone; bioreduction; asymmetric carbonyl reduction; kinetic resolution; enantiomeric ratio; kinetic model}}, language = {{eng}}, number = {{2}}, pages = {{98--102}}, publisher = {{Elsevier}}, series = {{Journal of Molecular Catalysis B: Enzymatic}}, title = {{Kinetic resolution of racemic 5,6-epoxy-bicyclo[2.2.1]heptane-2-one using genetically engineered Saccharomyces cerevisiae}}, url = {{https://lup.lub.lu.se/search/files/5510305/1393853.pdf}}, doi = {{10.1016/j.molcatb.2008.11.014}}, volume = {{58}}, year = {{2009}}, }