Ishida T, Matsui M, Inoue M, Hirano H, Yamashita M, Sugiyama K
Biochem Biophys Res Commun. 1983 Oct 31;116(2):486-91. doi: 10.1016/0006-291x(83)90549-1.
As part of a program to clarify the possible binding mode of tryptophan with thiamin coenzyme, the interaction between the indole and thiazolium rings has been studied by using a model compound, 2-(3,4-dimethylthiazolium-5-)ethyl indole-3-propionate, and the prominent stacking formation between both rings has been evidenced by the spectroscopic and X-ray crystallographic methods. The faster H-D exchange reaction of thiamin C2 proton observed in the presence of indole than in the lack would be resulted from the pi-pi charge-transfer interaction between the indole ring and the thiazolium ring of thiamin.
作为阐明色氨酸与硫胺素辅酶可能结合模式的项目的一部分，通过使用模型化合物2-(3,4-二甲基噻唑鎓-5-)-乙基吲哚-3-丙酸酯研究了吲哚环与噻唑环之间的相互作用，并且通过光谱和X射线晶体学方法证明了两个环之间存在显著的堆积结构。在有吲哚存在的情况下观察到硫胺素C2质子的H-D交换反应比没有吲哚时更快，这可能是由于吲哚环与硫胺素的噻唑环之间的π-π电荷转移相互作用所致。
