Efficient oxidation of 2′-deoxyguanosine by Mn-TMPyP/KHSO5 to imidazolone dIz without formation of 8-oxo-dG

被引：87

作者：

Vialas, C ^{[1
]}

Pratviel, G ^{[1
]}

Claparols, C ^{[1
]}

Meunier, B ^{[1
]}

机构：

[1] CNRS, Chim Coordinat Lab, F-31077 Toulouse 4, France

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1998年 / 120卷 / 45期

关键词：

D O I：

10.1021/ja981597+

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Oxidation of 2'-deoxyguanosine dG with the chemical nuclease Mn-TMPyP/KHSO5 leads within one minute to a nearly quantitative amount of 2-amino-5-[(2-deoxy-beta-D-erythro-pentofuranosyl)amino]-4H-imidazol-4-one (dIz or imidazolone for short) (90%) in a non-oxygen-dependent pathway and without formation of 8-oxo-dG. This new mechanism of dIz formation involves,as a crucial first step, the abstraction of two electrons from guanine by a high-valent porphyrin-Mn(V)=O species, leading to the dG(+) cation instead of the classical dG(.+) radical cation. We describe also the oxidation of imidazolone into the corresponding imidazolone N-oxide in the presence of KHSO5.

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页码：11548 / 11553

页数：6

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