TY - JOUR
T1 - Aliphatic hydroxylation by highly purified liver microsomal cytochrome P-450. Evidence for a carbon radical intermediate
AU - Groves, John T.
AU - McClusky, Gary A.
AU - White, Ronald E.
AU - Coon, Minor J.
N1 - Funding Information:
Acknowledgments. Financial support by the donors of the Petroleum Research Fund, administered by the American Chemical Society (JTG), The University of Michigan, National Science Foundation Grant PCM 76-14947 (MJC) and United States Public Health Services Grant AM-10339 (MJC) are gratefully acknowledged.
PY - 1978/3/15
Y1 - 1978/3/15
N2 - The oxidation of norbornane by a reconstituted liver cytochrome P-450 system affords exo- and endo-2-norborneol in a ratio of 3.4:1. The ratio of these products was found to be 0.76:1 when exo,exo,exo,exo-2,3,5,6-tetradueteronorbornane was oxidized. Analysis of the mass spectra of the products from the deuterated hydrocarbon showed that 25% of the exo-norborneol contained four deuterium atoms whereas 9% of the endo-norborneol contained three deuterium atoms. These results, which indicate a very large isotope effect ( kH kD = 11.5±1) and a significant amount of epimerization for the hydroxylation of norbornane by cytochrome P-450, suggest an initial hydrogen abstraction to give a carbon radical intermediate.
AB - The oxidation of norbornane by a reconstituted liver cytochrome P-450 system affords exo- and endo-2-norborneol in a ratio of 3.4:1. The ratio of these products was found to be 0.76:1 when exo,exo,exo,exo-2,3,5,6-tetradueteronorbornane was oxidized. Analysis of the mass spectra of the products from the deuterated hydrocarbon showed that 25% of the exo-norborneol contained four deuterium atoms whereas 9% of the endo-norborneol contained three deuterium atoms. These results, which indicate a very large isotope effect ( kH kD = 11.5±1) and a significant amount of epimerization for the hydroxylation of norbornane by cytochrome P-450, suggest an initial hydrogen abstraction to give a carbon radical intermediate.
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U2 - 10.1016/0006-291X(78)91643-1
DO - 10.1016/0006-291X(78)91643-1
M3 - Article
C2 - 656092
AN - SCOPUS:0017800253
SN - 0006-291X
VL - 81
SP - 154
EP - 160
JO - Biochemical and Biophysical Research Communications
JF - Biochemical and Biophysical Research Communications
IS - 1
ER -