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.
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.
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%).
White crystalline powder
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.
2′-Deoxyuridine (dU) 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).
An uridine derivative as therapeutic agent for treating allergy, cancer, infection and autoimmune disease