title: Stereocontrolled hydrolysis of the linoleic acid monoepoxide regioisomers catalyzed by soybean epoxide hydrolase.
abstract: Soybean fatty acid epoxide hydrolase (EC 3.3.2.3) was found to possess remarkable and unique stereochemical features. After complete hydrolysis, this enzyme converts racemic or enantiomerically enriched cis-9,10-epoxy-12(Z)-octadecenoic and cis-12,13-epoxyocta-9(Z)-decenoic acids, i.e. the two regioisomers of linoleic acid monoepoxides, into their corresponding 9R, 10R- and 12R, 13R-dihydrodiols with a high enantiomeric excess (> 90%). A straightforward chiral-phase HPLC technique was developed that gives an easy access to the stereochemistry of these reaction products. These results are discussed in terms of a possible model for the substrate binding site of this enzyme.
authors.affiliation: Institut de Biologie Moléculaire des Plantes (CNRS UPR 406), Institut de Botanique, Strasbourg, France.
authors.forename: E
authors.initials: E
authors.lastname: Blée
authors.forename: F
authors.initials: F
authors.lastname: Schuber
mesh_terms: D004851:Epoxide Hydrolases / Q000494:pharmacology*; D006868:Hydrolysis; D019787:Linoleic Acid; D008041:Linoleic Acids / Q000737:chemistry / Q000378:metabolism*; D008968:Molecular Conformation; D013025:Glycine max / Q000201:enzymology*
chemical_list: D008041:Linoleic Acids; D019787:Linoleic Acid; D004851:Epoxide Hydrolases