Base-Promoted Reaction of 5-Hydroxyuracil Derivatives with Peroxyl Radicals

被引：29

作者：

Amorati, Riccardo ^{[1
]}

Valgimigli, Luca ^{[1
]}

Pedulli, Gian Franco ^{[1
]}

Grabovskiy, Stanislav A. ^{[2
]}

Kabal'nova, Natalia N. ^{[2
]}

Chatgilialoglu, Chryssostomos ^{[2
]}

机构：

[1] Univ Bologna, Dept Organ Chem A Mangini, I-40126 Bologna, Italy

[2] CNR, ISOF, I-40129 Bologna, Italy

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 18期

关键词：

ANTIOXIDANT ACTIVITY; EFFICIENT SCAVENGER; 5-HYDROXY-6-METHYLURACIL; CONSTANTS; PHENOLS;

D O I：

10.1021/ol1017245

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of millimolar amounts of a weak base (pyridines) dramatically accelerates the reaction with peroxyl radicals of two biologically relevant uracil derivatives, 5-hydroxyuracil (HU) and 5-hydroxy-6-methyluracil (HMU). This is due to the formation of small amounts of the deprotonated form (pK(a) = 8.1-8.5 in water), which reacts with peroxyl radicals much faster than the parent undissociated form, via formal H-atom transfer from the OH in the 5 position.

引用

页码：4130 / 4133

页数：4

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