Kinetic resolution of racemic 5,6-epoxy-bicyclo[2.2.1]heptane-2-one using genetically engineered Saccharomyces cerevisiae

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Sammanfattning

(+)-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.
Originalspråkengelska
Sidor (från-till)98-102
TidskriftJournal of Molecular Catalysis B: Enzymatic
Volym58
Utgåva2
DOI
StatusPublished - 2009

Bibliografisk information

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)

Ämnesklassifikation (UKÄ)

  • Organisk kemi
  • Industriell bioteknik

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