Preparation of fatty epoxy alcohols using oat seed peroxygenase in nonaqueous media |
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Authors: | George J Piazza Thomas A Foglia Alberto Nuñez |
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Affiliation: | (1) USDA, ARS, ERRC, 19038 Wyndmoor, Pennsylvania |
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Abstract: | Peroxygenase is an enzyme of higher plants that is capable of using hydroperoxide and hydrogen peroxide for oxidation of a
double bond to an epoxide. A microsomal fraction was prepared from dry oat (Avena sativa) seeds. The peroxygenase activity of this fraction was tested using fatty acid hydroperoxide 2a 13(S)-hydroperoxy-9(Z), 11(E)-octadecadienoic acid] and its methyl ester 2b as sources of peroxygen. These were prepared by the action of soybean lipoxygenase on linoleic acid. A high-performance liquid
chromatographic assay was used to differentiate between peroxygen cleavage and peroxygen cleavage with accompanying double-bond
oxidation Higher activity was obtained with 2b compared to 2a, and peroxygen cleavage activity was observed in both aqueous and organic solvent media. Double-bond oxidation activity was
high only in aqueous media and nonpolar organic solvents. Structural elucidation of the epoxidized product showed it to be
the oxylipid, methyl cis-9,10-epoxy-13(S)-hydroxy-11(E)-octade-cenoate 4b, demonstrating specificity for epoxidation of the cis double bond. Trihydroxy product was not detected, demonstrating that the epoxide was not hydrolyzed. |
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Keywords: | Avena sativa epoxide hydroperoxide linoleic acid lipoxygenase peroxygenase |
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