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 language | English |
|---|---|
| Pages (from-to) | 155-167 |
| Number of pages | 13 |
| Journal | Bioorganic Chemistry |
| Volume | 5 |
| Issue number | 2 |
| DOIs | |
| Publication status | Published - Jan 1 1976 |
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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 journal › Article
}
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.
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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
AN - SCOPUS:0017156405
VL - 5
SP - 155
EP - 167
JO - Bioorganic Chemistry
JF - Bioorganic Chemistry
SN - 0045-2068
IS - 2
ER -