title: Enantioselectivity of the hydrolysis of linoleic acid monoepoxides catalyzed by soybean fatty acid epoxide hydrolase.
abstract: Soybean epoxide hydrolase efficiently catalyzes the hydration of the two positional isomers of linoleic acid monoepoxides into their corresponding vic-diols. Kinetic analysis of the progress curves, obtained at low substrate concentrations (i.e. [So] much less than Km), and analysis of the residual substrates by chiral-phase HPLC, indicate that the hydrolase is highly enantioselective, i.e. cis-9R,10S-epoxy-12(Z)-octadecenoic and cis-12R,13S-epoxy-9(Z)-octadecenoic acids are preferentially hydrolyzed (the enantioselectivity ratios are 15 and 28, respectively). Importantly, these two enantiomers are the one formed preponderantly by epoxidation of linoleic acid by peroxygenase, a hydroperoxide-dependent oxidase we have previously described in soybean (Blée, E., and Schuber, F., Biochem. Biophys. Res. Commun. (1990) 173, 1354-1360).
authors.affiliation: Institut de Biologie Moléculaire des Plantes (CNRS UPR-406), DECM, Strasbourg, France.
authors.forename: E
authors.initials: E
authors.lastname: Blee
authors.forename: F
authors.initials: F
authors.lastname: Schuber
mesh_terms: D002851:Chromatography, High Pressure Liquid; D004851:Epoxide Hydrolases / Q000378:metabolism*; D004852:Epoxy Compounds / Q000737:chemistry / Q000378:metabolism*; D006868:Hydrolysis; D007700:Kinetics; D019787:Linoleic Acid; D008041:Linoleic Acids / Q000737:chemistry / Q000378:metabolism*; D013025:Glycine max / Q000201:enzymology*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D004852:Epoxy Compounds; D008041:Linoleic Acids; D019787:Linoleic Acid; D004851:Epoxide Hydrolases