1989
DOI: 10.1021/tx00012a010
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Structural and conformational analyses of 8-hydroxy-2'-deoxyguanosine

Abstract: Oxidative DNA damage has been shown to involve formation of 8-hydroxy-2'-deoxyguanosine, which may serve as a mispairing lesion during cellular DNA replication. In order to assess the mutagenic potential of this DNA adduct, we examined the possible occurrence of several tautomeric forms and of different base conformations about the deoxyribose. Several spectroscopic and electronic absorption techniques were employed and showed structural changes occurring over a broad pH range. Two pKa's near pH 8 and 12 were … Show more

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Cited by 161 publications
(140 citation statements)
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“…Originally the lesion was reported as 8-hydroxyguanine; NMR studies (17) defined the structure as the tautomer 8-oxoG, with chemistry of the N-7 atom changed from that of a nucleophile to an amide nitrogen. In all biological systems examined, a proclivity for binding to or insertion of A is observed.…”
mentioning
confidence: 99%
“…Originally the lesion was reported as 8-hydroxyguanine; NMR studies (17) defined the structure as the tautomer 8-oxoG, with chemistry of the N-7 atom changed from that of a nucleophile to an amide nitrogen. In all biological systems examined, a proclivity for binding to or insertion of A is observed.…”
mentioning
confidence: 99%
“…The local maxima occured slightly below the pK a of imidazole and Tris, but this trend was not evident in the other two BGEs. The pK a of 8OHdG has been estimated as ~ 8 [ 22 ]. This is approximately one pH unit above the pH at which a marked decrease in peak width occured in Tris and imidazole BGE.…”
Section: Reduced Peak Widths As a Function Of Bge / Phmentioning
confidence: 92%
“…However, in that case, it was not caused by a tautomeric shift, since it appears that this oxidized base exists, under physiological conditions, in a single tautomeric N1-H, N7-H, 6,8-dioxo form [43][44][45]. The formation of the nonmutagenic Watson-Crick-type 8-oxoG : C pair with 8-oxodG in anti conformation and the mutagenic Hoogsteen-type 8-oxoG : A pair with 8-oxodG in syn conformation was proposed on the basis of NMR spectra of designed oligodeoxynucleotide complexes [46,47].…”
Section: Figure 4 Tautomeric Forms Of Igmentioning
confidence: 93%