Base-Promoted Reaction of 5-Hydroxyuracil Derivatives with Peroxyl Radicals
详细信息 查看全文
- 作者：Riccardo Amorati ; Luca Valgimigli ; Gian Franco Pedulli ; Stanislav A. Grabovskiy ; Natalia N. Kabal’ ; nova ; Chryssostomos Chatgilialoglu
- 刊名：Organic Letters
- 出版年：2010
- 出版时间：September 17, 2010
- 年：2010
- 卷：12
- 期：18
- 页码：4130-4133
- 全文大小：210K
- 年卷期：v.12,no.18(September 17, 2010)
- ISSN：1523-7052
文摘
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 (pKa = 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.