ELECTROPHILIC AMINATION OF GUANINE DERIVATIVES - MECHANISM FOR FORMATION OF 8-AMINOGUANINE DERIVATIVES

被引：18

作者：

KOHDA, K

BABA, K

KAWAZOE, Y

机构：

[1] Faculty of Pharmaceutical Sciences, Nagoya City University, Mizuho-ku, Nagoya, 467, Tanabedori

来源：

TETRAHEDRON | 1990年 / 46卷 / 05期

关键词：

D O I：

10.1016/S0040-4020(01)81962-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A study of the mechanism of 8-aminoguanosine formation in the reaction of guanosine with hydroxylamine-O-sulfonic acid (HAOS) revealed that the reaction proceeds in three steps; 1. electrophilic N-7 amination by HAOS, 2. nucleophilic C-8 hydroxyamination by NH2OH accompanied by elimination of the N-7 amino group and by aromatization, and finally 3. the reduction of the C-8 hydroxyamino group by NH2OH to give 8-aminoguanosine. The significance of formation of the 7-aminoguanosine intermediate is discussed briefly in relation to the reaction of carcinogenic arylamines and arylhydroxylamines with cellular DNA. © 1990.

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页码：1531 / 1540

页数：10

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