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. 1990 Dec 31;173(3):1354-60.
doi: 10.1016/s0006-291x(05)80937-4.

Stereochemistry of the epoxidation of fatty acids catalyzed by soybean peroxygenase

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Stereochemistry of the epoxidation of fatty acids catalyzed by soybean peroxygenase

E Blee et al. Biochem Biophys Res Commun. .

Abstract

The stereochemistry of C18 unsaturated fatty acids epoxidation catalyzed by detergent-solubilized and partially purified soybean peroxygenase was determined by chiral phase HPLC. Linoleic acid was oxidized into 9, 10- and 12,13-cis-epoxyoctadecenoic acids with a high enantiofacial selectivity. A 5.2:1 and 2.3:1 ratio respectively in favor of the 9(R), 10(S)- and 12(R), 13(S)-epoxy enantiomers was observed. These epoxy-derivatives of linoleic acid have the chirality of metabolites known to be involved in plant defense against fungi. This finding is of importance in establishing a physiological role for the peroxygenase.

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