Macrocyclic enzyme model systems. Catalytic activity of cyclic peptides involving hydrophobic segments.
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概要
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In order to develop an effective hydrolase model, BCP-1 was synthesized and its kinetic behavior investigated. The corresponding linear hexapeptide was prepared by the solid phase method and subjected to cyclization by the azide method. BCP-1 enhanced the hydrolysis of <I>p</I>-nitrophenyl carboxylates bearing a long alkyl chain. The pH-rate profile for the hydrolysis of <I>p</I>-nitrophenyl hexadecanoate (PNPP) as effected by BCP-1 was not of a bell-shaped type but a sigmoid, from which the kinetic p<I>K</I><SUB>a</SUB> value was estimated as 12.3. The initial reaction rate was found to level off beyond a certain range of substrate concentration (saturation-type kinetics), the kinetic data being analyzed on the basis of Michaelis-Menten scheme. The large hydrophobic binding ability of BCP-1 toward PNPP (<I>K</I><SUB>m</SUB>(app) \simeq10<SUP>−6</SUP>M) was attributed to its double-layered bicyclic structure. The Hammett plot for the hydrolysis of substituted phenyl hexadecanoates gave a satisfactory linear correlation. Consequently, the acyl transfer from the bound substrate to the imidazole anion of the histidyl residue of BCP-1 was referred to the rate-determining step. The large negative entropy change for the acyl transfer step seems to indicate that the Michaelis complex does not have a conformation favorable for such acyl transfer process. The catalytic effectiveness (<I>k</I><SUB>cat</SUB>⁄<I>K</I><SUB>m</SUB>(app)) for the BCP-1 catalysis in PNPP hydrolysis is comparable to that for enzymatic hydrolysis.
- 公益社団法人 日本化学会の論文
著者
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Murakami Yukito
Department Of Chemical Science And Technology Faculty Of Engineering Kyushu University
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Matsumoto Kiyoshi
Department Of Applied Chemistry Faculty Of Engineering Kanagawa University
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Nakano Akio
Department of Chemistry, Faculty of Science, Kyushu University
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Iwamoto Kiyoshi
Department of Industrial Chemistry, Faculty of Engineering, Nagasaki University
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