Journal of the American Chemical Society p. 3334 - 3336 (1984)
Update date:2022-08-02
Topics:
Falck, J. R.
Manna, S.
Jacobson, Harry R.
Estabrook, R. W.
Chacos, N.
Capdevila, Jorge
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.
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