8-Oxoguanine

8-Oxoguanine[1]
IUPAC name

2-Amino-7,9-dihydro-1H-purine-6,8-dione
Other names

8-Oxo-7,8-dihydroguanine
Identifiers
CAS number 5614-64-2 Y
PubChem 119315
ChemSpider 106574 Y
MeSH 8-hydroxyguanine
ChEBI CHEBI:44605 Y
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C5H5N5O2
Molar mass 167.13 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

8-Oxoguanine (8-hydroxyguanine, 8-oxo-Gua, or OH8Gua) is one of the most common DNA lesions resulting from reactive oxygen species [2] and can result in a mismatched pairing with Adenine resulting in G to T and C to A substitutions in the genome.[3] In humans, it is primarily repaired by the DNA glycosylase OGG1. It can be caused by ionizing radiation, in connection with oxidative metabolism.

References

  1. ^ 8-hydroxyguanine - Compound Summary, PubChem
  2. ^ S. Kanvah, et al., Oxidation of DNA: Damage to Nucleobases; Acc. Chem. Res. 2010, 43(2), 280-287
  3. ^ Cheng KC, Cahill DS, Kasai H, Nishimura S, Loeb LA (1992 Jan 5). "8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G→T and A→C substitutions.". J Biol Chem. 267 (1): 166–72. PMID 1730583. 
Nucleic acid constituents
Nucleobase
Nucleoside
Nucleotide
(Nucleoside monophosphate)
Nucleoside diphosphate
Nucleoside triphosphate
biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i