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Stereocomplementary Bioreduction of Alpha,beta-unsaturated Dicarboxylic Acids and Dimethyl Esters Using Enoate Reductases: Enzyme- and Substrate-based Stereocontrol

Overview
Journal Org Lett
Specialties Biochemistry
Chemistry
Date 2007 Nov 23
PMID 18031047
Citations 18
Authors
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Abstract

Asymmetric bioreduction of alpha,beta-unsaturated dicarboxylic acids, such as 2-methylmaleic/fumaric and 2-methylenesuccinic acid, as well as the corresponding dimethyl esters, using three cloned enoate reductases furnished 2-methylsuccinic acid or dimethyl 2-methylsuccinate, respectively. Opposite stereoisomeric products were obtained in up to >99% ee either by choice of the enzyme or by using E/Z-configurated substrates. Cofactor-recycling systems (NADH/FDH/formate, NADH/GDH/glucose or NADPH/G6PDH/glucose-6-phosphate) only worked in presence of a divalent metal ion, such as Ca2+, Mg2+, or Zn2+.

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