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| 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 | |
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3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.012.232 |
| MeSH | Deoxyuridine |
| UNII | |
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| |
| Properties | |
| C9H12N2O5 | |
| Molar mass | 228.202 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Deoxyuridine (dU) is acompound and anucleoside. 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 andTrifluridine are variants of deoxyuridine used asantiviral drugs. They are similar enough to be incorporated as part ofDNA replication, but they possess side groups on theuracil component (aniodine and a CF3 group, respectively), that preventbase pairing. A known use ofdU is as a precursor in the synthesis ofEdoxudine.[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]
