Cytosine glycol

Cytosine glycol
Names
IUPAC name
4-Amino-5,6-dihydroxy-5,6-dihydro-2(1H)-pyrimidinone
Other names
5,6-Dihydroxy-5,6-dihydrocytosine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C4H7N3O3/c5-2-1(8)3(9)7-4(10)6-2/h1,3,8-9H,(H3,5,6,7,10) COPY
    Key: KJFJEAILAVCIQJ-UHFFFAOYSA-N
  • C1(C(NC(=O)N=C1N)O)O
Properties
C4H7N3O3
Molar mass 145.118 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Cytosine glycols are intermediate unstable products of cytosine oxidation. These, in turn, are thought to undergo deamination to uracil glycol, dehydration to 5-hydroxycytosine, or both deamination and dehydration to 5-hydroxyuracil.[1] Its name indicates its major structural nature: a glycol derivative of cytosine, as the apparent 1,2-dihydroxylation of its alkene region.

The lifetime of cytosine glycols are enhanced in double-stranded DNA compared to the free nucleoside.[2]

References

  1. ↑ Sébastien Tremblay; J. Richard Wagner (2008). "Dehydration, deamination and enzymatic repair of cytosine glycols from oxidized poly(dG-dC) and poly(dI-dC)". Nucleic Acids Res. 36 (1): 284–293. doi:10.1093/nar/gkm1013. PMC 2248729. PMID 18032437.
  2. ↑ Tremblay S, Douki T, Cadet J, Wagner JR (1999). "2'-Deoxycytidine glycols, a missing link in the free radical-mediated oxidation of DNA". J Biol Chem. 274 (30): 20833–8. doi:10.1074/jbc.274.30.20833. PMID 10409624.
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