5-Hydroxyuracil

5-Hydroxyuracil
Names
IUPAC name
2,4,5-Pyrimidinetriol
Other names
5-Hydroxy-2,4(1H,3H)-pyrimidinedione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.119 Edit this at Wikidata
EC Number
  • 207-829-9
UNII
  • InChI=1S/C4H4N2O3/c7-2-1-5-4(9)6-3(2)8/h1,7H,(H2,5,6,8,9)
    Key: OFJNVANOCZHTMW-UHFFFAOYSA-N
  • c1c(c(nc(n1)O)O)O
Properties
C4H4N2O3
Molar mass 128.087 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

5-Hydroxyuracil is an oxidized form of cytosine that is produced by the oxidative deamination of cytosines by reactive oxygen species. It does not distort the DNA molecule and is bypassed by replicative DNA polymerases. It can miscode for adenine and is potentially mutagenic.

References

  1. ↑ Varatharasa Thiviyanathan; Anoma Somasunderam; David E. Volka & David G. Gorenstein (2005). "5-Hydroxyuracil can form stable base pairs with all four bases in a DNA duplex". Chem. Commun. (3): 400–402. doi:10.1039/B414474K. PMID 15645051.
  2. ↑ Helmut Greim; Richard J. Albertini (2012). The Cellular Response to the Genotoxic Insult: The Question of Threshold for Genotoxic Carcinogens. Royal Society of Chemistry. ISBN 9781849731775. Retrieved July 20, 2015.