title: Spiroiminodihydantoin nucleoside formation from 2'-deoxyguanosine oxidation by [(18)O-labeled] singlet molecular oxygen in aqueous solution.
abstract: The main singlet molecular oxygen ((1)O(2)) oxidation products of free 2'-deoxyguanosine (dGuo) in aqueous solution were identified as a pair of diastereomeric spiroiminodihydantoin 2'-deoxyribonucleosides (dSp) together with 8-oxo-7,8-dihydro-2'-deoxyguanosine (8-oxodGuo). In the present work, evidence is provided from (18)[(1)O(2)] and H(2) (18)O labeling experiments, using HPLC-ESI-MS/MS, that the formation of dSp is explained by the addition of water to a reactive quinonoid intermediate, and a second reaction pathway leading to dSp involves (1)O(2) oxidation of initially generated 8-oxodGuo.
authors: Departamento de Bioquímica e Biologia Molecular, Setor de Ciências Biológicas, Universidade Federal do Paraná, Curitiba, Brazil.
authors: Glaucia Regina
authors: GR
authors: Martinez
authors: Jean-Luc
authors: JL
authors: Ravanat
authors: Jean
authors: J
authors: Cadet
authors: Marisa Helena Gennari
authors: MH
authors: de Medeiros
authors: Paolo
authors: P
authors: Di Mascio
mesh_terms: D002851:Chromatography, High Pressure Liquid; D003849:Deoxyguanosine / Q000737:chemistry*; D006151:Guanosine / Q000031:analogs & derivatives* / Q000737:chemistry; D006827:Hydantoins / Q000737:chemistry; D007700:Kinetics; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010103:Oxygen Isotopes; D026082:Singlet Oxygen; D012996:Solutions; D021241:Spectrometry, Mass, Electrospray Ionization; D013141:Spiro Compounds / Q000737:chemistry*; D053719:Tandem Mass Spectrometry; D014867:Water
chemical_list: D006827:Hydantoins; D010103:Oxygen Isotopes; D012996:Solutions; D013141:Spiro Compounds; C408822:spiroiminodihydantoin; D014867:Water; D006151:Guanosine; D026082:Singlet Oxygen; D003849:Deoxyguanosine