Micellar activation of nucleophilic reactivity of coenzyme A and glutathione toward p-nitrophenyl acetate.
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概要
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The reaction of coenzyme A(CoASH) and glutathione (GSH) with <I>p</I>-nitrophenyl acetate was studied in aqueous media at 30 °C. The reaction is highly accelerated in the presence of hydrophobic aggregates such as hydrophobic oligocations and CTABr micelles. Nonionic and anionic micelles were ineffective. The p<I>K</I><SUB>a</SUB> of CoASH is lowered by 0.5 p<I>K</I><SUB>a</SUB> unit in 2 mM of CTABr, while that of GSH is hardly affected. The second-order rate constant for CoASH is improved (290-fold) more than that of GSH (100-fold), relative to the nonmicellar system. Enhanced reactivities are efficiently suppressed by addition of KCl. These results are the first example of the marked activation of sulfhydryl coenzymes by the micellar microenvironment, and explicable by the concept of <I>hydrophobic ion pairs</I>: the coenzymes are bound onto the cationic micelle and the thiol anions form ion pairs with surfactant cations at the relatively hydrophobic environment of the micelle.
- 公益社団法人 日本化学会の論文
著者
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Kunitake Toyoki
Department Of Chemical Engineering & Technology Faculty Of Engineering Kyushu University
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Shinkai Seiji
Department Of Applied Chemistry Faculty Of Engineering Kyushu University
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