Multifunctional Hydrolytic Catalyses. 8. Remarkable Acceleration of the Hydrolysis of p-Nitrophenyl Acetate by Micellar Bifunctional Catalysts

Toyoki Kunitake, Yoshio Okahata, Tetsuo Sakamoto

研究成果: Contribution to journalArticle査読

65 被引用数 (Scopus)

抄録

Surfactant molecules which contain the hydroxamate and imidazole functions were synthesized, and their catalytic actions in aqueous cetyltrimethylammonium bromide micelles were examined for the hydrolysis of p-nitrophenyl acetate at 30 °C. The catalysis proceeded mainly via acylation and imidazole-catalyzed deacylation at the hydroxamate group. Both of these processes were remarkably accelerated in the case of bifunctional micelles, due to activation of anionic nucleophiles in cationic micellar environments. The overall catalytic efficiency exceeded even that of α-chymotrypsin at pH 8 and was more than 5000 times higher than that of imidazole. Micellar monofunctional catalysts and a nonmicellar bifunctional catalyst were much less effective. Therefore, the combination of bifunctionality and micellar microenvironments was essential for the highly efficient catalysis.

本文言語英語
ページ(範囲)7799-7806
ページ数8
ジャーナルJournal of the American Chemical Society
98
24
DOI
出版ステータス出版済み - 11 1 1976

All Science Journal Classification (ASJC) codes

  • 触媒
  • 化学 (全般)
  • 生化学
  • コロイド化学および表面化学

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