oxo8dG – 8-Oxo-2'-deoxyguanosine; 8-hydroxy-2'-deoxyguanosine

Name
WID oxo8dG View in model
Name 8-Oxo-2'-deoxyguanosine; 8-hydroxy-2'-deoxyguanosine View in model
Traditional name 2-amino-9-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3,7-dihydropurine-6,8-dione
IUPAC name 2-amino-9-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,7,8,9-tetrahydro-3H-purine-6,8-dione
Cross references ChEBI: 121726, PubChem: 24671802
 
Classification
Type modified_deoxyribonucleoside View in model
 
Structure
Empirical formula (pH 7.5) H13C10N5O5
SMILES (pH 7.5) C1C(C(OC1N2C3=C(C(=O)N=C(N3)N)NC2=O)CO)O
Charge (pH 7.5) 0
Is hydrophobic False View in model
Molecular weight (Da) 283.24 View in model
van der Waals volume 
(pH 7.5; Å3 molecule‑1)		 222.53
pI 4.97
logP -2.47
logD (pH 7.5) -2.65
 
Function
Reaction participant View in model
 
Comments
Comments most common DNA base lesion [PUB_0479]; 92-520 lesions per 10^7 bases [PUB_0479]; recognized by endonuclease III, FPG, UNG [PUB_0473]
References

  1. Guetens G, De Boeck G, Highley M, van Oosterom AT, de Bruijn EA. Oxidative DNA damage: biological significance and methods of analysis. Crit Rev Clin Lab Sci 39, 331-457 (2002). WholeCell: PUB_0479, PubMed: 12385502

  2. Hatahet Z, Kow YW, Purmal AA, Cunningham RP, Wallace SS. New substrates for old enzymes. 5-Hydroxy-2'-deoxycytidine and 5-hydroxy-2'-deoxyuridine are substrates for Escherichia coli endonuclease III and formamidopyrimidine DNA N-glycosylase, while 5-hydroxy-2'-deoxyuridine is a substrate for uracil DNA N-glycosylase. J Biol Chem 269, 18814-20 (1994). WholeCell: PUB_0473, PubMed: 8034633
 
Metadata
Created 2012-10-01 15:07:05
Last updated 2012-10-01 15:12:27