Characterization of the dehydro-guanidinohydantoin oxidation product of guanine in a dinucleotide

被引:29
作者
Chworos, A [1 ]
Seguy, C [1 ]
Pratviel, G [1 ]
Meunier, B [1 ]
机构
[1] CNRS, Chim Coordinat Lab, F-31077 Toulouse 04, France
关键词
D O I
10.1021/tx0200717
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The study of the biological consequences of oxidative damage to DNA requires the characterization of DNA lesions at a molecular level. The oxidation of guanine in the dinucleoside monophosphate, d(GpT), by a metal-oxo porphyrin produces a dehydroguanidinohydantoin derivative. The(1)H NMR spectrum of this oxidized guanine derivative is reported. The structure was confirmed by the chemical transformation of the dehydroguanidinohydantoin derivative into a linear oxaluric acid derivative upon hydrolysis at ambient temperature. The proposed mechanism of formation of the dehydro-guanidinohydantoin derivative is in agreement with the labeling experiments performed with (H2O)-O-18.
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收藏
页码:1643 / 1651
页数:9
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