CHEMISTRY: Smoking Catalysts

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Science  05 Apr 2002:
Vol. 296, Issue 5565, pp. 15d
DOI: 10.1126/science.296.5565.15d

Catalyzing reactions in physiological solvents has seemed to be reserved for protein and RNA enzymes, but Dickerson and Janda show that a metabolite—in this case, a nicotine derivative that can persist in the blood of heavy smokers—can do so, too. Nornicotine can accelerate the aldol condensation reaction for a variety of substrates in phosphate buffer solutions near physiological pH. In the authors' proposed mechanism, which is similar to that for a type I aldolase, condensation products will form so long as carbon-carbon bond formation can compete with the rapid hydrolysis of an enamine intermediate. Although the overall rates are still low, the action of such compounds could affect glycolysis and the metabolism of drugs containing ketone groups.—PDS

J. Am. Chem. Soc. 10.1021/ja017774f (2002).

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