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

In English

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.

Publiceringsår

2009

Språk

Engelska

Sidor

98-102

Publikation/Tidskrift/Serie

Journal of Molecular Catalysis B: Enzymatic

Volym

58

Issue

2

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