Kinetic resolution of racemic 5,6-epoxy-bicyclo[2.2.1]heptane-2-one using genetically engineered Saccharomyces cerevisiae
Författare
Summary, in English
(+)-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.
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.
Publiceringsår
2009
Språk
Engelska
Sidor
98-102
Publikation/Tidskrift/Serie
Journal of Molecular Catalysis B: Enzymatic
Volym
58
Issue
2
Fulltext
- Available as PDF - 323 kB
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Dokumenttyp
Artikel i tidskrift
Förlag
Elsevier
Ämne
- Organic Chemistry
- Industrial Biotechnology
Nyckelord
- Baker's yeast
- Saccharomyces cerevisiae
- epoxide
- racemic epoxy ketone
- bioreduction
- asymmetric carbonyl reduction
- kinetic resolution
- enantiomeric ratio
- kinetic model
Status
Published
ISBN/ISSN/Övrigt
- ISSN: 1873-3158