8-Oxoguanine

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8-Oxoguanine[1]
8-Oxoguanine.png
Identifiers
CAS number 5614-64-2 YesY
PubChem 119315
ChemSpider 106574 YesY
MeSH 8-hydroxyguanine
ChEBI CHEBI:44605 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C5H5N5O2
Molar mass 167.13 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
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.

8-oxoG (syn) in a Hoogsteen base pair with dA (anti)
For comparison here is a standard (non-mutagenic) GC base pair with both bases in the anti configuration of the bond between base and sugar.

References[edit]

  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 (Jan 5, 1992). "8-Hydroxyguanine, an abundant form of oxidative DNA damage, causes G→T and C→A substitutions.". J Biol Chem. 267 (1): 166–72. PMID 1730583.