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Microsomal P450-catalyzed N-dealkylation of N,N-dialkylanilines: evidence for a C(alpha)-H abstraction mechanism

Bhakta, Mehul N.
Wimalasena, Kandatege
Authors
Bhakta, Mehul N.
Wimalasena, Kandatege
Other Names
Wichita State University. Department of Chemistry
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2002-03-06
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Article
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Research Support, U.S. Gov't, P.H.S.
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Research Projects
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Citation
Journal of the American Chemical Society. 2002 Mar 6; 124(9): 1844-5.
Abstract
The early proposal that P450-catalyzed N-dealkylation of N,N-dialkylamines proceeds through a single-electron-transfer (SET) mechanism was later challenged in favor of the C(alpha)-H abstraction mechanism. In the present study, a series of N-alkyl-N-cyclopropyl-p-chloroaniline probes have been used to examine whether the P450-catalyzed N-dealkylations proceed through a C(alpha)-H abstraction and/or a SET mechanism, using phenobarbital-induced rat liver microsomal P450 enzymes as a model system. While the findings are highly consistent with a C(alpha)-H abstraction mechanism, further experimental evidence may be necessary to completely rule out the SET mechanism.
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Publisher
American Chemical Society
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Journal of the American Chemical Society
J. Am. Chem. Soc.
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ISSN
0002-7863
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