Effect of the Carbamoyl Group of Pyridine Coenzyme on the Interaction with Tryptophan : Crystallographic, Energy Calculation and Proton Nuclear Magnetic Resonance Studies Using Model Compounds(Physical,Chemical)
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概要
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In order to elucidate the effect of the carbamoyl group on the indole-nicotinamide ring stacking interaction in pyridine coenzyme-tryptophan molecular association, the crystal structure of l-[3-(indol-3-yl)propyl]pyridinium (IC3P) bromide has been analyzed and compared with that of l-[3-(indol-3-yl)propyl]nicotinamide (IC3NIC) sulfate. In contrast to IC3NIC sulfate, no direct interaction between the indole and pyridinium rings was observed in IC3P bromide. This result clearly shows that the carbamoyl group takes an important role in the stacking interaction of the nicotinamide ring with the indole ring, as has also been suggested by empirical energy calculations and measurements of absorption spectra. The contribution of the carbamoyl group to the interaction has been further investigated by proton nuclear magnetic resonance measurements using simple intermolecular (skatole l-methylnicotinamide and skatole-1-ethylpyridinium) and intramolecular (IC3P bromide and IC3NIC sulfate) models. Analyses of the temperature dependences in the chemical shifts (δ) of the pyridinium aromatic protons yielded values for the parameters of the interaction: dδ_T/dT, K (association constant), and the thermodynamic parameters ΔH, ΔS and ΔG. The difference in the stacking interaction between indole-pyridinium and indole-nicotinamide rings, and the contribution of the carbamoyl group to the interaction are discussed based on the parameters values obtained.
- 社団法人日本薬学会の論文
- 1986-12-25
著者
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土井 光暢
大阪薬大
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石田 寿昌
大阪薬大
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石田 寿昌
Osaka University of Pharmaceutical Sciences
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伊藤 美穂
Department Of Physical Chemistry Osaka College Of Pharmacy
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伊藤 美穂
Osaka University of Pharmaceutical Sciences
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土井 充暢
Osaka University of Pharmaceutical Sciences
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井上 正敏
Osaka University of Pharmaceutical Sciences
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井上 正敏
大阪薬大
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石田 寿晶
大阪薬科大学
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Doi Mitsunobu
Department Of Physical Chemistry Osaka University Of Pharmaceutical Sciences
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井上 正敏
Department Of Physical Chemistry Osaka University Of Pharmaceutical Sciences
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