Catalytic hydrolysis of p-nitrophenyl esters in the presence of representative ammonium aggregates. Specific activation of a cholesteryl nucleophile bound to a dialkylammonium bilayer membrane.
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概要
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Catalytic hydrolysis of <I>p</I>-nitrophenyl esters (acetate and nonanoate) by hydroxamate and imidazole nucleophiles was studied at 30 °C in the presence of aqueous aggregates of single-chain (hexadecyl), double-chain (didodecyl and dioctadecyl) and triple-chain (trioctyl) ammonium amphiphiles. These three types of ammonium salts give rise to very different aggregate morphologies. The rate constant of ester cleavage by the nucleophiles was enhanced several hundred folds in the presence of these hydrophobic aggregates. Simple long-chain nucleophiles possessed esterolytic reactivities which reflect the hydrophobic microenvironment of the respective aggregates: single-chain<double-chain<triple-chain. On the other hand, the cholesteryl ester of imidazolecarboxylic acid showed an especially high reactivity when bound to the didodecylammonium bilayer. Cholic acid-derived nucleophiles showed normal reactivity patterns. Apparently, specific binding of the cholesterol derivative to the bilayer is responsible for the unusual catalytic behavior.
- 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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Ando Reiko
Department of Organic Syntheis, Faculty of Engineering, Kyushu University
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Okahata Yoshio
Department of Applied Chemistry, Kyushu University 36
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