dhpURA – 5'-dihydroxypentyluracil

Name
WID dhpURA View in model
Name 5'-dihydroxypentyluracil View in model
Traditional name 5-(4,5-dihydroxypentyl)-1,3-dihydropyrimidine-2,4-dione
IUPAC name 5-(4,5-dihydroxypentyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione
Cross references PubChem: 24612588
 
Classification
Type modified_nucleobase View in model
 
Structure
Empirical formula (pH 7.5) H14C9N2O4
SMILES (pH 7.5) C1=C(C(N(C(N1)=O)[H])=O)CCCC(O)CO
Charge (pH 7.5) 0
Is hydrophobic False View in model
Molecular weight (Da) 214.22 View in model
van der Waals volume 
(pH 7.5; Å3 molecule‑1)
190.84
pI 3.56
logP -1.19
logD (pH 7.5) -1.19
 
Function
Reaction participant DNA base alkylation (5-hydroxymethyluracil ==> 5'-dihydroxypentyluracil; 1,2-Butylene glycol)
[c]: butylene_glycol + hm5URAdhpURA + H2O
View in model
 
Comments
Comments occurs in bacteriophage DNA [PUB_0477]; in bacteriophage SP15 up to 60% thymidine replaced by dhpdU [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 15:06:54
Last updated 2012-10-01 15:12:03