Intramolecular isotope effects associated with meta-hydroxylation of biphenyl catalyzed by cytochrome P-450
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′-[ 2H 4]-biph...
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Veröffentlicht in: | Biochemical and biophysical research communications 1984-02, Vol.118 (3), p.867-872 |
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Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | 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′-[
2H
4]-biphenyl was found to be 77.3% ± 1.9. The intramolecular isotope effects associated with 3,3′-[
2H
2]-biphenyl and 3,5-[
2H
2]-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. |
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ISSN: | 0006-291X 1090-2104 |
DOI: | 10.1016/0006-291X(84)91475-X |