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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38 Citations (Scopus)

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
StatePublished - 1984

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Oxygenation
Arachidonic Acid
Liver
Cytochrome P-450 Enzyme System
Rats
Chromatographic analysis
Hydroxyeicosatetraenoic Acids
Cytochromes b5
NADPH-Ferrihemoprotein Reductase
Acids
Epoxidation
Epoxy Compounds
Phenobarbital
NADP
Chromatography
Esters
Proteins
11,12-epoxy-5,8,14-eicosatrienoic acid
5,6-epoxy-8,11,14-eicosatrienoic acid
14,15-epoxy-5,8,11-eicosatrienoic acid

ASJC Scopus subject areas

  • Chemistry(all)

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Absolute configuration of epoxyeicosatrienoic acids (EETs) formed during catalytic oxygenation of arachidonic acid by purified rat liver microsomal cytochrome P-450. / Falck, J R; Manna, S.; Jacobson, Harry R.; Estabrook, R. W.; Chacos, N.; Capdevila, Jorge.

In: Journal of the American Chemical Society, Vol. 106, No. 11, 1984, p. 3334-3336.

Research output: Contribution to journalArticle

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