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Aqueous Aldol Catalysis by a Nicotine Metabolite

Dickerson, Tobin J ; Janda, Kim D

Journal of the American Chemical Society, 2002-04, Vol.124 (13), p.3220-3221 [Periódico revisado por pares]

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Título:
Aqueous Aldol Catalysis by a Nicotine Metabolite
Autor: Dickerson, Tobin J ; Janda, Kim D
Assuntos: Acetone - chemistry ; Benzaldehydes - chemistry ; Catalysis ; Chemistry ; Exact sciences and technology ; Kinetics ; Kinetics and mechanisms ; Nicotine - analogs & derivatives ; Nicotine - chemistry ; Organic chemistry ; Proline - chemistry ; Pyrrolidines - chemistry ; Reactivity and mechanisms ; Substrate Specificity ; Water - chemistry
É parte de: Journal of the American Chemical Society, 2002-04, Vol.124 (13), p.3220-3221
Notas: istex:3BD48AB55279E9670A9F57176151E925B395FCC8
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ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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Descrição: 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 catalysis. Substrate compatibility of this catalyst and its implications in vivo are discussed.
Editor: Washington, DC: American Chemical Society
Idioma: Inglês

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