gluTHY – a-glutamylthymine

Name
WID gluTHY View in model
Name a-glutamylthymine View in model
Traditional name 2-{[(2,4-dioxo-1,3-dihydropyrimidin-5-yl)methyl]amino}pentanedioic acid
IUPAC name 2-{[(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methyl]amino}pentanedioic acid
Cross references PubChem: 75229612, CAS: 76567-27-6
 
Classification
Type modified_nucleobase View in model
 
Structure
Empirical formula (pH 7.5) H13C10N3O6
SMILES (pH 7.5) C1(=CNC(=O)NC1=O)CNC(C(O)=O)CCC(O)=O
Charge (pH 7.5) -1
Is hydrophobic False View in model
Molecular weight (Da) 271.23 View in model
van der Waals volume 
(pH 7.5; Å3 molecule‑1)		 224.66
pI 2.59
logP -4.36
logD (pH 7.5) -7.26
 
Function
Reaction participant DNA base amination (5-hydroxymethyluracil ==> a-glutamylthymine; L-glutamate)
[c]: GLU + H + hm5URA ⇒ gluTHY + H2O		 View in model
 
Comments
Comments occurs in bacteriophage DNA [PUB_0477]; in bacteriophage PhiW-14 up to 50% thymidine replaced by gludT [PUB_0478];
References

  1. Gommers-Ampt JH, Borst P. Hypermodified bases in DNA. FASEB J 9, 1034-42 (1995). WholeCell: PUB_0478, PubMed: 7649402

  2. Warren RA. Modified bases in bacteriophage DNAs. Annu Rev Microbiol 34, 137-58 (1980). WholeCell: PUB_0477, PubMed: 7002022
 
Metadata
Created 2012-10-01 15:06:59
Last updated 2012-10-01 15:12:13