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Stereocontrolled hydrolysis of the linoleic acid monoepoxide regioisomers catalyzed by soybean epoxide hydrolase

, : Stereocontrolled hydrolysis of the linoleic acid monoepoxide regioisomers catalyzed by soybean epoxide hydrolase. European Journal of Biochemistry 230(1): 229-234

Soybean fatty acid epoxide hydrolase (EC 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 ( gt 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.


PMID: 7601104

DOI: 10.1111/j.1432-1033.1995.0229i.x

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