Absolute configuration of epoxyeicosatrienoic acids (EETs) formed during catalytic oxygenation of arachidonic acid by purified rat liver microsomal cytochrome P-450

J R Falck, S. Manna, Harry R. Jacobson, R. W. Estabrook, N. Chacos, Jorge Capdevila

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Abstract

Incubation of arachidonic acid with a reconstituted enzymatic system containing a purified preparation of the major, phenobarbital-inducible form of rat liver microsomal cytochrome P-450, NADPH, cytochrome b5, and NADPH-cytochrome P-450 reductase affords as the principal products four regioisomeric cis-epoxides: 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids (EETs). Their absolute configurations were established by conversion to the corresponding hydroxyeicosatetraenoic acid (HETE) methyl esters, derivatization with dehydroabiethylisocyanate, and chromatographic analysis. Except for 5,6-EET, the cytochrome P-450 catalyzed epoxidation is highly enantioselective.

Original languageEnglish (US)
Pages (from-to)3334-3336
Number of pages3
JournalJournal of the American Chemical Society
Volume106
Issue number11
Publication statusPublished - 1984

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ASJC Scopus subject areas

  • Chemistry(all)

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