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Molecular Pharmacology, Vol 13, 634-639, Copyright © 1977 by the American Society for Pharmacology and Experimental Therapeutics

Intramolecular Determination of Substituent Effects in Hydroxylations Catalyzed by Cytochrome P-450

LEONARD M. HJELMELAND 1, LEWIS ARONOW 1, and JAMES R. TRUDELL 1

1 Departments of Pharmacology and Anesthesia, Stanford University, Stanford, California 94305

Hydroxylation of monosubstituted 1,3-diphenylpropanes by rat liver microsomes leads predominantly to a mixture of the isomeric benzylic alcohols at positions 1 and 3. Quantitation of the relative concentrations of these alcohols can be achieved by combined gas chromatography-mass fragmentography. p-Methyl, p-trifluoromethyl, and p-fluoro substituents yield product distributions which clearly indicate an electrophilic mechanism for the hydroxylation reaction.

Note:
ACKNOWLEDGMENTS The authors gratefully acknowledge the expert assistance of Dr. Elaine Herron and the Finnigan Corporation in obtaining mass fragmentograms.

Submitted on December 6, 1976
Accepted on March 3, 1977




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Copyright © 1977 by the American Society for Pharmacology and Experimental Therapeutics