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 language | English (US) |
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Pages (from-to) | 637-640 |
Number of pages | 4 |
Journal | Journal of medicinal chemistry |
Volume | 31 |
Issue number | 3 |
DOIs | |
State | Published - Mar 1 1988 |