TY - JOUR
T1 - Absolute Configuration of Epoxyeicosatrienoic Acids (EETs) Formed during Catalytic Oxygenation of Arachidonic Acid by Purified Rat Liver Microsomal Cytochrome P-450
AU - Falck, J R
AU - Manna, S.
AU - Jacobson, Harry R.
AU - Estabrook, R. W.
AU - Chacos, N.
AU - Capdevila, Jorge
PY - 1984/11
Y1 - 1984/11
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=0011246902&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0011246902&partnerID=8YFLogxK
U2 - 10.1021/ja00323a046
DO - 10.1021/ja00323a046
M3 - Article
AN - SCOPUS:0011246902
SN - 0002-7863
VL - 106
SP - 3334
EP - 3336
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 11
ER -