- Base-promoted reaction of 5-hydroxyuracil derivatives with peroxyl radicals.
Base-promoted reaction of 5-hydroxyuracil derivatives with peroxyl radicals.
Organic letters (2010-08-28)
Riccardo Amorati, Luca Valgimigli, Gian Franco Pedulli, Stanislav A Grabovskiy, Natalia N Kabal'nova, Chryssostomos Chatgilialoglu
PMID20795653
ABSTRACT
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.
MATERIALS