Characterization of the dehydro-guanidinohydantoin oxidation product of guanine in a dinucleotide.
The study of the biological consequences of oxidative damage to DNA requires the characterization of DNA lesions at a molecular level. The oxidation of guanine in the dinucleoside monophosphate, d(GpT), by a metal-oxo porphyrin produces a dehydro-guanidinohydantoin derivative. The (1)H NMR spectrum of this oxidized guanine derivative is reported. The structure was confirmed by the chemical transformation of the dehydro-guanidinohydantoin derivative into a linear oxaluric acid derivative upon hydrolysis at ambient temperature. The proposed mechanism of formation of the dehydro-guanidinohydantoin derivative is in agreement with the labeling experiments performed with H(2)(18)O.
Chworos
Arkadiusz
A
Laboratoire de Chimie de Coordination du CNRS, 205 route de Narbonne, 31077 Toulouse, Cedex 04, France.
Seguy
Christel
C
Pratviel
Geneviève
G
Meunier
Bernard
B
D004247:DNA / Q000737:chemistry; D015226:Dinucleoside Phosphates / Q000737:chemistry*; D006146:Guanidines / Q000737:chemistry*; D006827:Hydantoins / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D010084:Oxidation-Reduction; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism
D015226:Dinucleoside Phosphates; D006146:Guanidines; D006827:Hydantoins; C475501:dehydroguanidinohydantoin; D004247:DNA