Deoxyuridine

Deoxyuridine
Skeletal formula of deoxyuridine
Ball-and-stick model of the deoxyuridine molecule
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.012.232 Edit this at Wikidata
MeSH Deoxyuridine
UNII
  • 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 checkY
    Key: MXHRCPNRJAMMIM-SHYZEUOFSA-N checkY
  • 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
  • O=C/1NC(=O)N(\C=C\1)[C@@H]2O[C@@H]([C@@H](O)C2)CO
Properties
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).
☒N verify (what is checkY☒N ?)

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]

  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.