Catalytic efficiency of cationic micellar catalysts bearing a mercapto group as the reaction center.
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概要
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In order to clarify micro-environmental effects on the reactivity of mercapto groups in enzymes, cationic surfactants bearing a mercapto group, <I>N</I>-hexadecyl-<I>N</I><SUP>α</SUP>-(3-trimethylammoniopropionyl)-L-cysteinamide bromide (CM·Cys-1) and <I>N</I>-dodecyl-<I>N</I><SUP>α</SUP>-(6-trimethylammoniohexanoyl)-L-cysteinamide bromide (CM·Cys-2), were synthesized and their kinetic behavior investigated. The surfactants above their critical micelle concentrations markedly catalyzed the decomposition <I>p</I>-nitrophenyl hexanoate (PNPH) and acetate (PNPA), the concentrationrate profiles being found to be those for typical micelle-catalyzed reactions. The rate constants for the degradation of PNPH as catalyzed by CM·Cys-1 and -2 in the micellar phase are 0.482 and 0.197 s<SUP>−1</SUP>, respectively, in 9.8% (v/v)ethanol–1.0%(v/v)dioxane–1.0%(v/v)methanol-water at 30.0±0.1 °C, pH 8.65, and μ0.10 (KCl). The difference in catalytic activity can be attributed partly to the micro-environmental effect on the p<I>K</I><SUB>a</SUB> value of the mercapto group lying at the reaction center. The rate constants for the thiolate anions (true reactive species) of CM·Cys-1 and -2 to react with PNPH were identical with each other irrespective of the nature of the surfactants. The electrostatic effect provided by the cationic charge in the Stern layer, which acts to reduce the p<I>K</I><SUB>a</SUB> value of the reactive mercapto group, seems to play a more important role than the desolvation effect on the thiolate anion by the hydrophobic field.
- 公益社団法人 日本化学会の論文
著者
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Murakami Yukito
Department Of Chemical Science And Technology Faculty Of Engineering Kyushu University
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Matsumoto Kiyoshi
Department Of Applied Chemistry Faculty Of Engineering Kanagawa University
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Nakano Akio
Department of Chemistry, Faculty of Science, Kyushu University
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Iwamoto Kiyoshi
Department of Industrial Chemistry, Faculty of Engineering, Nagasaki University
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Iwamoto Kiyoshi
Department of Organic Synthesis, Faculty of Engineering, Kyushu University
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