Base-promoted reaction of 5-hydroxyuracil derivatives with peroxyl radicals.
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.
Amorati
Riccardo
R
Department of Organic Chemistry A. Mangini, University of Bologna, Via S. Giacomo 11, I-40126 Bologna, Italy.
Valgimigli
Luca
L
Pedulli
Gian Franco
GF
Grabovskiy
Stanislav A
SA
Kabal'nova
Natalia N
NN
Chatgilialoglu
Chryssostomos
C
D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry; D010545:Peroxides / Q000737:chemistry*; D014498:Uracil / Q000031:analogs & derivatives* / Q000737:chemistry
D010545:Peroxides; C045975:5-hydroxyuracil; D014498:Uracil; D010100:Oxygen