Deoxyuridine

Deoxyuridine
Names
	IUPAC name 2′-Deoxyuridine
	Systematic IUPAC name 1-[(2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4(1H,3H)-dione
Identifiers
CAS Number	951-78-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16450 ;
ChEMBL	ChEMBL353955 ;
ChemSpider	13118 ;
ECHA InfoCard	100.012.232
MeSH	Deoxyuridine
PubChem CID	640;
UNII	W78I7AY22C ;
CompTox Dashboard (EPA)	DTXSID30883621 ;
	InChI InChI=1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1 Key: MXHRCPNRJAMMIM-SHYZEUOFSA-N ; InChI=1/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1 Key: MXHRCPNRJAMMIM-SHYZEUOFBK;
	SMILES O=C/1NC(=O)N(\C=C\1)[C@@H]2O[C@@H]([C@@H](O)C2)CO;
Properties
Chemical formula	C9H12N2O5
Molar mass	228.202
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Deoxyuridine (dU) is a compound and a nucleoside. It belongs to a class of compounds known as Pyrimidine 2'-deoxyribonucleosides^[1] and closely resembles the chemical composition of uridine but without the presence of the 2' hydroxyl group. Idoxuridine and Trifluridine are variants of deoxyuridine used as antiviral drugs. They are similar enough to be incorporated as part of DNA replication, but they possess side groups on the uracil component (an iodine and a CF₃ group, respectively), that prevent base pairing. A known use of dU is as a precursor in the synthesis of Edoxudine.^[2]

This compound exists in all living organisms and can become part of DNA in both prokaryotic and eukaryotic cells through two mechanisms. The first is the removal of an amino group from cytosine to result in uracil and the second is the non-intentional incorporation of pyrimidine where thymine belongs in the DNA, resulting in dUMP.^[3]

UMP synthase deficiency is a metabolic disorder in humans that involves deoxyuridine. Deoxyuridine can be toxic. It has also been found in several foods, which makes it a useful indicator for diseases through consumption of those foods.^[4]

References

^ "Human Metabolome Database: Showing metabocard for Deoxyuridine (HMDB0000012)". www.hmdb.ca. Retrieved 2019-12-05.
^ "2'-deoxyuridine (CHEBI:16450)". www.ebi.ac.uk. Retrieved 2019-12-05.
^ Richards, R. G.; Sowers, L. C.; Laszlo, J.; Sedwick, W. D. (1984). "The occurrence and consequences of deoxyuridine in DNA". Advances in Enzyme Regulation. 22: 157–185. doi:10.1016/0065-2571(84)90013-x. ISSN 0065-2571. PMID 6147963.
^ "Human Metabolome Database: Showing metabocard for Deoxyuridine (HMDB0000012)". www.hmdb.ca. Retrieved 2019-12-05.

[1] "Human Metabolome Database: Showing metabocard for Deoxyuridine (HMDB0000012)". www.hmdb.ca. Retrieved 2019-12-05.

[2] "2'-deoxyuridine (CHEBI:16450)". www.ebi.ac.uk. Retrieved 2019-12-05.

[3] Richards, R. G.; Sowers, L. C.; Laszlo, J.; Sedwick, W. D. (1984). "The occurrence and consequences of deoxyuridine in DNA". Advances in Enzyme Regulation. 22: 157–185. doi:10.1016/0065-2571(84)90013-x. ISSN 0065-2571. PMID 6147963.

[4] "Human Metabolome Database: Showing metabocard for Deoxyuridine (HMDB0000012)". www.hmdb.ca. Retrieved 2019-12-05.

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