Multifunctional hydrolytic catalysis. VI. Catalytic hydrolysis of p-nitrophenyl acetate by N-(4-imidazolylmethyl)benzohydroxamic acid

Toyoki Kunitake, Yoshio Okahata, Toyohide Tahara

研究成果: Contribution to journalArticle査読

12 被引用数 (Scopus)

抄録

A bifunctional catalyst, N-(4-imidazolylmethyl)benzohydroxamic acid, was synthesized from benzohydroxamic acid and chloromethylimidazole, and used for the hydrolysis of p-nitrophenyl acetate. The reaction proceeded via the formation of the acetyl hydroxamate and its subsequent decomposition. The deacylation step was shown to be general base-catalyzed by the intramolecular imidazole group on the basis of the deuterium solvent kinetic isotope effect of 2.0. The efficiency of water attack on the acetyl hydroxamate was enhanced 130-fold by the imidazole group. The catalytic process is compared with the reactions of related monofunctional compounds, and finally its significance as a model of the charge relay system is discussed.

本文言語英語
ページ(範囲)155-167
ページ数13
ジャーナルBioorganic Chemistry
5
2
DOI
出版ステータス出版済み - 1 1 1976

All Science Journal Classification (ASJC) codes

  • 生化学
  • 分子生物学
  • 創薬
  • 有機化学

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