Cytosine glycol

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

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

↑ 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'-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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[MyUser_Ncbi.nlm.nih.gov_July_20_2015c-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.

[NCBI2-2] "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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Cytosine glycol

Topic: Chemistry

References