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

Toyoki Kunitake, Yoshio Okahata, Toyohide Tahara

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)155-167
Number of pages13
JournalBioorganic Chemistry
Volume5
Issue number2
DOIs
Publication statusPublished - Jan 1 1976

Fingerprint

Catalysis
Hydrolysis
Deuterium
Isotopes
Decomposition
Catalysts
Kinetics
Water
4-nitrophenyl acetate
imidazole
benzohydroxamic acid

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

Cite this

Multifunctional hydrolytic catalysis. VI. Catalytic hydrolysis of p-nitrophenyl acetate by N-(4-imidazolylmethyl)benzohydroxamic acid. / Kunitake, Toyoki; Okahata, Yoshio; Tahara, Toyohide.

In: Bioorganic Chemistry, Vol. 5, No. 2, 01.01.1976, p. 155-167.

Research output: Contribution to journalArticle

@article{1374279d2de84e90a17709758b2df9a6,
title = "Multifunctional hydrolytic catalysis. VI. Catalytic hydrolysis of p-nitrophenyl acetate by N-(4-imidazolylmethyl)benzohydroxamic acid",
abstract = "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.",
author = "Toyoki Kunitake and Yoshio Okahata and Toyohide Tahara",
year = "1976",
month = "1",
day = "1",
doi = "10.1016/0045-2068(76)90004-3",
language = "English",
volume = "5",
pages = "155--167",
journal = "Bioorganic Chemistry",
issn = "0045-2068",
publisher = "Academic Press Inc.",
number = "2",

}

TY - JOUR

T1 - Multifunctional hydrolytic catalysis. VI. Catalytic hydrolysis of p-nitrophenyl acetate by N-(4-imidazolylmethyl)benzohydroxamic acid

AU - Kunitake, Toyoki

AU - Okahata, Yoshio

AU - Tahara, Toyohide

PY - 1976/1/1

Y1 - 1976/1/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0017156405&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0017156405&partnerID=8YFLogxK

U2 - 10.1016/0045-2068(76)90004-3

DO - 10.1016/0045-2068(76)90004-3

M3 - Article

VL - 5

SP - 155

EP - 167

JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

SN - 0045-2068

IS - 2

ER -