Stereochemical studies on the cytochrome P-450 catalyzed oxidation of (S)-nicotine to the (S)-nicotine. DELTA. 1'(5')-iminium species

…, A Trevor, N Castagnoli Jr

Index: Peterson, Lisa A.; Trevor, Anthony; Castagnoli, Neal Journal of Medicinal Chemistry, 1987 , vol. 30, # 2 p. 249 - 254

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Citation Number: 66

Abstract

Lisa A. Peterson, Anthony Trevor, and Neal Castagnoli, Jr.* Department of Pharmaceutical Chemistry, School of Pharmacy, University of California, San Francisco, San Francisco, California 94143. Received March 20, 1986 ... Mammals metabolize the tobacco alkaloid (S)-nicotine primarily to the lactam (S)-cotinine by a pathway involving an initial cytochrome P-450 catalyzed two-electron oxidation at the prochiral 5'-carbon atom. The stereochemical course of this oxidation was ...