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