Investigation of hydrolytic deamination of 1-(-hydroxy-1-phenylethyl)adenosine

被引：31

作者：

Barlow, T ^{[1
]}

Ding, JM ^{[1
]}

Vouros, P ^{[1
]}

Dipple, A ^{[1
]}

机构：

[1] NORTHEASTERN UNIV,BARNETT INST,DEPT CHEM,BOSTON,MA 02115

来源：

CHEMICAL RESEARCH IN TOXICOLOGY | 1997年 / 10卷 / 11期

关键词：

D O I：

10.1021/tx970091m

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The ring nitrogen of adenosine reacts at both the alpha-(benzylic) and beta-carbons of styrene oxide to form 1-substituted products. The 1-(2-hydroxy-1-phenylethyl)adenosines formed by oxirane ring opening at the alpha-position are prone to an unusually facile hydrolytic deamination. By conducting hydrolysis reactions in [O-18]water and analyzing the reaction products by electrospray mass spectrometry, we find that deamination occurs by direct attack of water at the beta-position of the adenine ring system with displacement of the exocyclic amino group.

引用

页码：1247 / 1249

页数：3

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