Record number :
1713828
Title of article :
Kinetic resolution of racemic 5,6-epoxy-bicyclo[2.2.1]heptane-2-one using genetically engineered Saccharomyces cerevisiae
Author/Authors :
Carlquist، نويسنده , , Magnus G. Olsson، نويسنده , , Cecilia and Bergdahl، نويسنده , , Basti and van Niel، نويسنده , , Ed W.J. and Gorwa-Grauslund، نويسنده , , Marie F. and Frejd، نويسنده , , Torbjِrn، نويسنده ,
Issue Information :
روزنامه با شماره پیاپی سال 2009
Pages :
5
From page :
98
To page :
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 biocatalyst was demonstrated to be significantly inactivated within 24 h, thus restricting the reaction to low concentration. 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.
Keywords :
kinetic resolution , Bioreduction , Racemic epoxy ketone , epoxide , Kinetic model , Enantiomeric ratio , Bakerיs yeast , Saccharomyces cerevisiae , Asymmetric carbonyl reduction
Journal title :
Journal of Molecular Catalysis B Enzymatic
Serial Year :
2009
Link To Document :
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