Coenzyme models. VII. Micellar catalysis of acid-catalyzed hydration of 1-dodecyl-1,4-dihydronicotinamide.
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概要
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The acid-catalyzed hydration reaction of 1-dodecyl-1,4-dihydronicotinamide was examined in cationic(CTAB) and anionic (SDS) micelles. The H<SUB>3</SUB>O<SUP>+</SUP>-catalysis(<I>k</I><SUB>H</SUB> was negligibly small in the presence of the CTAB micelle and 225–521 M<SUP>−1</SUP> s<SUP>−1</SUP> in the presence of the SDS micelle, the difference being about 10<SUP>7</SUP>-fold. The catalysis by carboxylic acids (<I>k</I><SUB>HA</SUB>) was considerably suppressed in the CTAB micelle, but was promoted in the SDS micelle, suggesting the development of a cationic charge on a nitrogen atom of dihydropyridine at the rate-determining step. Brönsted plots for log<I>k</I><SUB>HA</SUB> in the CTAB and SDS micelles <I>vs.</I> p<I>K</I><SUB>a</SUB> of carboxylic acids gave straight lines with the slope of −0.8, the line for SDS being higher by two orders of magnitude than that for CTAB. These results indicate that a cationic charge (<I>e.g.,</I> the lysine residue of alcohol dehydrogenase located very close to the bound NADH) may protect the NADH from hydration decay.
- 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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Ando Reiko
Department of Organic Syntheis, Faculty of Engineering, Kyushu University
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