Stereocomplementary bioreduction of alpha,beta-unsaturated dicarboxylic acids and dimethyl esters using enoate reductases: enzyme- and substrate-based stereocontrol.
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+.
Stueckler
Clemens
C
Department of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, 8010 Graz, Austria.
Hall
Mélanie
M
Ehammer
Heidemarie
H
Pointner
Eva
E
Kroutil
Wolfgang
W
Macheroux
Peter
P
Faber
Kurt
K
D003998:Dicarboxylic Acids / Q000737:chemistry*; D004952:Esters / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry; D009243:NAD / Q000737:chemistry; D009249:NADP / Q000737:chemistry; D010088:Oxidoreductases / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D003998:Dicarboxylic Acids; D004952:Esters; D009243:NAD; D009249:NADP; D010088:Oxidoreductases; D005947:Glucose