THY_GLYC – thymine glycol

Name
WID THY_GLYC View in model
Name thymine glycol View in model
Traditional name thymine glycol
IUPAC name 5,6-dihydroxy-5-methyl-1,3-diazinane-2,4-dione
Cross references ChEBI: 29128, PubChem: 8146714
 
Classification
Type modified_nucleobase View in model
 
Structure
Empirical formula (pH 7.5) H8C5N2O4
SMILES (pH 7.5) CC1(C(NC(=O)NC1=O)O)O
Charge (pH 7.5) 0
Is hydrophobic False View in model
Molecular weight (Da) 160.13 View in model
van der Waals volume 
(pH 7.5; Å3 molecule‑1)		 129.76
pI 1.93
logP -1.86
logD (pH 7.5) -1.96
 
Function
Reaction participant DNA radiation (gamma-ray) induced base oxidation (thymine ==> thymine glycol; hydroxyl radical)
gamma_radiation[e] + (2) hydroxyl_radical[c] + THY[c] ⇒ THY_GLYC[c]		 View in model
 
Comments
Comments recognized by endonuclease III, FPG, UNG [PUB_0473]
References

  1. 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 15:07:08
Last updated 2012-10-01 15:12:34