Stereoselective, biocatalytic reductions of alpha-chloro-beta-keto esters.
Eighteen known and putative reductases from baker's yeast (Saccharomyces cerevisiae) were tested for the ability to reduce a series of alpha-chloro-beta-keto esters. In nearly all cases, it was possible to produce at least two of the four possible alpha-chloro-beta-hydroxy ester diastereomers with high optical purities. The utility of this approach was demonstrated by reducing ethyl 2-chloroacetoacetate to the corresponding syn-(2R,3S)-alcohol on a multigram scale using whole cells of an Escherichia coli strain overexpressing a single yeast reductase identified from the screening studies.
Kaluzna
Iwona A
IA
Department of Chemistry, University of Florida, Gainesville, Florida 32611, USA.
Feske
Brent D
BD
Wittayanan
Weerawut
W
Ghiviriga
Ion
I
Stewart
Jon D
JD
D000429:Alcohol Oxidoreductases / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*; D002384:Catalysis; D004926:Escherichia coli / Q000378:metabolism; D004952:Esters / Q000737:chemistry / Q000378:metabolism; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry* / Q000378:metabolism; D010084:Oxidation-Reduction; D010088:Oxidoreductases / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*; D012441:Saccharomyces cerevisiae / Q000201:enzymology* / Q000235:genetics; D013237:Stereoisomerism; D013379:Substrate Specificity
D004952:Esters; D006843:Hydrocarbons, Chlorinated; D010088:Oxidoreductases; D000429:Alcohol Oxidoreductases