Description
2'-Deoxyuridine is a natural deoxynucleoside, which can be directly used to prepare combined deoxynucleoside drugs or used as chemical reagents for biochemical research. At the same time, it can be used as an intermediate to synthesize some antiviral nucleoside drugs and molecular markers, such as 8-bromo-2-deoxyuridine and 8-hydroxy-2-deoxyuridine from 2'-Deoxyuridine.
Physical properties
2'-Deoxyuridine is a white or off-white powdered solid with a melting
point of 167 to 169 °C. Its boiling point is roughly estimated to be
370.01°C. It is slightly soluble in water, DMSO, and slightly soluble in
methanol when heated.
synthesis
The precursor 3,5-(toluoyl)-2-deoxy-(N1,N3-15N)-uridine (1) was synthesized according to Schiesser et al.4 In a round bottom flask 1 (76 mg, 0.16 mmol, 1.0 eq.) was dissolved in dry MeOH (2.1 mL) and K2CO3 (49 mg, 0.35 mmol, 2.2 eq.) was added. The suspension was stirred at 40 °C for 6 h. The solvent was removed by rotary evaporation. The residue was then suspended in H2O (5 mL) and extracted with DCM (5 mL). The aqueous layer was then concentrated to dryness, redissolved in H2O and subjected to RP-HPLC (0% to 20% MeCN in water in 45 min, 5 mL/min). [15N2]-dU as a white solid (31 mg, 0.13 mmol, 84%).
Description
2'-Deoxyuridine is an intermediate in the synthesis of thymidylate, which is a precursor for DNA synthesis. It has been shown to inhibit the enzymatic activity of enzymes responsible for synthesizing uridine and thymidylate, leading to neuronal death. 2'-Deoxyuridine has been used as a fluorescence probe for nucleic acids and as a polymerase chain reaction (PCR) substrate. It is also known to bind with toll-like receptor 4 (TLR4), which is involved in inflammatory responses.
Chemical Properties
White crystalline powder
Uses
2'-Deoxyuridine is frequently halogenated to create thymidine analogues useful for studies of DNA synthesis and degradation mechanisms. Derivatized 2'-Deoxyuridines used as labeling substrates include chloro-2'-deoxyuridine (CldU), bromodeoxyuridine (BrdU) and/or iododeoxyuridine (IdU). Other useful analogues of 2'-deoxyuridine include 5-ethynyl-2'-deoxyuridine (DdU) and 5-hydroxymethyl-2'-deoxyuridine (HmdU). Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemias due to vitamin B12 and folate deficiencies. Deoxyuridine (dU) is used to indirectly determine if there are sufficient levels of folate and cobalamin in cell or tissue samples.
Uses
An uridine derivative as therapeutic agent for treating allergy, cancer, infection and autoimmune disease
Definition
ChEBI: 2'-deoxyuridine is a pyrimidine 2'-deoxyribonucleoside having uracil as the nucleobase. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is functionally related to a uracil.
Biological Activity
2'-deoxyuridine is frequently halogenated to create thymidine analogues useful for studies of dna synthesis and degradation mechanisms.
