Synthesis of monoepoxides of arachidonic, eicosapentaenoic, and docosahexaenoic acids

Kuklev, D.V.; Rybin, V.G.; Imbs, A.B.; Bezuglov, V.V.; Kuklev, D.V; Rybin, V.G; Imbs, A.B; Bezuglov, V.V

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Synthesis of monoepoxides of arachidonic, eicosapentaenoic, and docosahexaenoic acids

Kuklev, D.V.; Rybin, V.G.; Imbs, A.B.; Bezuglov, V.V.

Bioorganicheskaia Khimiia 19(11): 1122-1127

1993

ISSN/ISBN: 0132-3423

PMID: 8285925

Document Number: 416517

A practical synthesis of cis-monoepoxides from free arachidonic 20:4 (n - 6), eicosapentaenoic 20: 5 (n - 3) and docosahexaenoic 22: 6 (n - 3) acids, their Cytochrome P-450 epoxygenase metabolites, is described. The free polyunsaturated fatty acids (PUFA) were oxidized each by 1.25 eq. m-chloroperbenzoic acid in ethanol to give a mixture of PUFAs' mono-epoxy derivatives (45%) which was separated by HPLC and the individual isomers were characterised by mass spectrometry. All regioisomers of the free PUFAs' cis-monoepoxides were thus obtained.