The pH-dependent role of superoxide in riboflavin-catalyzed photooxidation of 8-oxo-7,8-dihydroguanosine

被引：127

作者：

Luo, WC ^{[1
]}

Muller, JG ^{[1
]}

Burrows, CJ ^{[1
]}

机构：

[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 18期

关键词：

D O I：

10.1021/ol0161763

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The riboflavin-catalyzed photooxidation of 2',3',5'-tri-O-acetyl-8-oxo-7,8-dihydroguanosine generates a radical intermediate that is competitively trapped by H2O, O-2(-.), or O-2. The products of H2O trapping have been previously described as the spiroiminodihydantoin (pH greater than or equal to 7) and iminoallantoin/guanidinohydantoin (pH < 7) nucleosides. Trapping by 02- leads to the oxaluric acid (pH less than or equal to 7) and imidazolone (pH greater than or equal to 8.6) pathways (R", R" = H or 2,3,5-tri-O-Ac-ribofuranosyl). The pH-dependent role of superoxide was probed using Mn-SOD and compared to guanosine and 8-methoxyguanosine photooxidation.

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页码：2801 / 2804

页数：4

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