Preferential C1' hydrogen abstraction by a uracilyl radical in a DNA-RNA hybrid

被引：40

作者：

Sugiyama, H ^{[1
]}

Fujimoto, K ^{[1
]}

Saito, I ^{[1
]}

机构：

[1] KYOTO UNIV,DEPT SYNTHET CHEM & BIOL CHEM,KYOTO 60601,JAPAN

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 46期

关键词：

D O I：

10.1016/S0040-4039(97)10108-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photoreaction of 5-halouracil contained in a DNA-RNA hybrid which forms an A form type structure was examined and the photoreactivity of this hybrid was compared with that for a DNA duplex. The results indicated that in a DNA-RNA hybrid, the uracilyl-5-yl radical preferentially abstracts the C1' H of the deoxyribose that is on the 5' side of the radical. NOE experiments of DNA hexamer and DNA-RNA hybrid demonstrated that there appears to be no correlation between the distances and the selectivity of H abstraction. In order to examine the origin of the selectivity of Il abstraction, a putative transition state for H abstraction in a DNA duplex and a DNA-RNA hybrid was constructed and the conformational energy required to achieve their transition states was evaluated. The results provide a qualitative explanation of conformation-dependent H abstraction by the uracilyl-5-yl radical in a DNA duplex and DNA-RNA hybrid. (C) 1997 Elsevier Science Ltd.

引用

页码：8057 / 8060

页数：4

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