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Intramolecular isotope effects associated with meta-hydroxylation of biphenyl catalyzed by cytochrome P-450.

作者信息

Swinney D C, Howald W N, Trager W F

出版信息

Biochem Biophys Res Commun. 1984 Feb 14;118(3):867-72. doi: 10.1016/0006-291x(84)91475-x.

DOI:10.1016/0006-291x(84)91475-x
PMID:6704111
Abstract

Intramolecular isotope effects and the degree of deuterium retention were determined for the meta-hydroxylation of biphenyl as catalyzed by microsomal cytochrome P-450 obtained from rats pretreated with phenobarbital. The percent deuterium retention after meta-hydroxylation of 3,5,3',5'-[2H4]-biphenyl was found to be 77.3% +/- 1.9. The intramolecular isotope effects associated with 3,3'-[2H2]-biphenyl and 3,5-[2H2]-biphenyl were found to be 0.90 +/- .05 and 1.05 +/- .06, respectively. These data demonstrate conclusively that a direct insertion or abstraction mechanism is not operable in the meta-hydroxylation of biphenyl and suggest the possibility of an addition-rearrangement mechanism as opposed to initial and direct arene oxide formation.

摘要

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