Prototropic molecular-zwitterionic tautomerism of xanthine and hypoxanthine

被引：35

作者：

Kondratyuk, IV ^{[1
]}

Samijlenko, SP ^{[1
]}

Kolomiets, IM ^{[1
]}

Hovorun, DM ^{[1
]}

机构：

[1] Ukrainian Acad Sci, Inst Mol Biol & Genet, UA-03143 Kiev, Ukraine

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2000年 / 523卷

关键词：

xanthine; hypoxanthine; molecular-zwitterionic tautomerism; AM1; calculations; H-1 NMR spectroscopy;

D O I：

10.1016/S0022-2860(99)00385-3

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The prototropic molecular-zwitterionic tautomerism of xanthine (Xan) and hypoxanthine (Hyp) was investigated by the semi-empirical quantum-chemical AM1 method. Geometric, energetic and electronic features of their complete molecular-zwitterionic families of tautomers were established. The influence of the environment with universal solvatation mechanism on the tautomeric equilibrium was evaluated at Onzager approximation. The comparison of the calculations with the H-1 NMR data favors the N7H Xan and the N9H Hyp tautomers in anhydrous DMSO solutions. The possible biochemical role of tautomeric (especially zwitterionic) forms of Xan and Hyp is discussed. Stabilizing influences of environment and specific interactions with proteins on rare tautomeric forms are considered. (C) 2000 Elsevier Science B.V. All rights reserved.

引用

页码：109 / 118

页数：10

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