Regio- and Stereochemical Studies on the α-Carbon Oxidation of (S)-Nicotine by Cytochrome P-450 Model Systems

Lisa A. Peterson, Neal Castagnoli

Research output: Contribution to journalArticle

26 Scopus citations

Abstract

Results from previous studies indicate that rabbit liver microsomal cytochrome P-450 catalyzes the C-5’ two-electron oxidation of (S)-nicotine stereoselectivity with preferential loss of the pro-(E)-hydrogen atom trans to the pyridine ring. We now have examined the regio- and stereochemical features of the oxidation of (S)-nicotine by peroxides in the presence of various hemoproteins and by electrochemical and photochemical methods. None of these systems gave rise to the stereochemical outcomes observed with the cytochrome P-450 mediated reaction. The results of these studies are interpreted as additional evidence for the formation of a highly ordered complex between (S)-nicotine and cytochrome P-450 that directs the regio- and diasterioselective α-carbon oxidation of this substrate.

Original languageEnglish (US)
Pages (from-to)637-640
Number of pages4
JournalJournal of Medicinal Chemistry
Volume31
Issue number3
DOIs
StatePublished - Mar 1 1988

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