title: Stereoselective, biocatalytic reductions of alpha-chloro-beta-keto esters.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Florida, Gainesville, Florida 32611, USA.
authors.forename: Iwona A
authors.initials: IA
authors.lastname: Kaluzna
authors.forename: Brent D
authors.initials: BD
authors.lastname: Feske
authors.forename: Weerawut
authors.initials: W
authors.lastname: Wittayanan
authors.forename: Ion
authors.initials: I
authors.lastname: Ghiviriga
authors.forename: Jon D
authors.initials: JD
authors.lastname: Stewart
mesh_terms: 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
chemical_list: D004952:Esters; D006843:Hydrocarbons, Chlorinated; D010088:Oxidoreductases; D000429:Alcohol Oxidoreductases