Stacking interaction of indole ring with thiazolium ring and effect for H-D exchange reaction of thiamin

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...

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Published inBiochemical and biophysical research communications Vol. 116; no. 2; pp. 486 - 491
Main Authors Ishida, Toshimasa, Matsui, Miyuki, Inoue, Masatoshi, Hirano, Hiroshi, Yamashita, Mayumi, Sugiyama, Kazuaki
Format Journal Article
LanguageEnglish
Published United States Elsevier Inc 31.10.1983
Subjects
Chemical Phenomena
Chemistry, Physical
Crystallography
Indoles
Spectrophotometry, Ultraviolet
Thiazoles
X-Rays
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Summary: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 π-π chargetransfer interaction between the indole ring and the thiazolium ring of thiamin.
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ISSN:0006-291X
1090-2104
DOI:10.1016/0006-291X(83)90549-1