Cytosine glycol

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Names
IUPAC name

4-Amino-5,6-dihydroxy-5,6-dihydro-2(1H)-pyrimidinone

Other names

5,6-Dihydroxy-5,6-dihydrocytosine

Identifiers

CAS Number

* 13484-98-5

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:29127

ChemSpider |

* 145962

PubChem CID

* 166830

InChI

* 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

SMILES

* C1(C(NC(=O)N=C1N)O)O

Properties

Chemical formula

| 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

Tracking categories (test):

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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]

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. PMID 18032437.
2. ↑ "2'-Deoxycytidine glycols, a missing link in the free radical-mediated oxidation of DNA". J Biol Chem 274 (30): 20833–8. 1999. doi:10.1074/jbc.274.30.20833. PMID 10409624.

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*[CID]: Compound ID