トリプトファンの生体分子との相互作用に関する構造化学的研究
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Tryptophan, an indispensable amino acid, is not only the constituent of protein, but also replaced into biologically active molecules such as indole-3-acetic acid and serotonin. In order to clarify the physiological function of these indole compounds, their interaction modes, especially the indole ring which they contain commonly, with biomolecules must be known at atomic level. The present review has been discussed on the interaction of indole ring with vitamin B coenzymes (pyridine, flavin, thiamine, and pyridoxal) and with nucleic acid bases (adenine, guanine, and pyrimidine), based on X-ray crystal structural and solution spectroscopic studies. A significant characteristic commonly observed in the interactions of indole compounds with pyridine, flavin, and thiamin coenzymes is the prominent π-π stacking formation including partial charge-transfer, and this suggests that in addition to the importance of tryptophan residue for enzyme-apoenzyme interaction, their catalytic reactions are accelerated by the partial , π-electron transfer from indole ring. On the other hand, the conformational analysis of tryptophan-pyridoxal Schiff base has shown a reasonable metabolic pathway according to Dunathn's hypothesis. In contrast with neutral adenine and guanine bases, their protonated or methylated ones are strongly bound with indole ring through prominent π-π stacking interactions, providing a clue for understanding the selective recognition mechanism of nucleic acid bases by tryptophan. Indole ring also binds with pyrimidine bases by stacking interactions. The specific π-π stacking formation commonly observed in the interactions of indole ring with these important biomolecules, which is stabilized by strong molecular orbital couplings between respective aromatic rings in addition to electrostatic and/or dipole-dipole ones, is served for diverse biological reactions.
- 社団法人日本薬学会の論文
- 1988-06-25
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