Aqueous aldol catalysis by a nicotine metabolite

TJ Dickerson, KD Janda

Index: Dickerson, Tobin J.; Janda, Kim D. Journal of the American Chemical Society, 2002 , vol. 124, # 13 p. 3220 - 3221

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Citation Number: 174

Abstract

Nornicotine, an endogenous tobacco alkaloid and minor nicotine metabolite, can catalyze aldol reactions at physiological pH. Catalysis appears to be due to a covalent enamine mechanism, an unprecedented reaction with small organic molecule catalysts in aqueous buffer. Kinetic parameters for nornicotine as well as other related alkaloids were measured and demonstrate that both the pyrrolidine and pyridine rings are critical for optimal ...