5-Methoxyuridine

Description

5-Methoxyuridine is an intermediate in the biosynthesis of pyrimidines and is also used as a precursor for other compounds. 5-Methoxyuridine is an analog of Uridine and is used as a reagent in the synthesis of 5-OMe-UDP, a potent and selective P2Y6-receptor agonist. It inhibits messenger RNA (mRNA) production in bacteria by interfering with sequence recognition and binding sites within the ribosome and preventing.

Chemical Properties

Solid

Uses

5-Methoxyuridine is an analog of Uridine (U829910) and is used as a reagent in the synthesis of 5-OMe-UDP, a potent and selective P2Y6-receptor agonist.

Definition

ChEBI: A derivative of uridine, bearing an additional methoxy substituent at position 5 on the uracil ring.

Synthesis

5-Hydroxyuridine was synthesized by the method described by T. Ueda. 5-Hydroxyuridine (30 mg) was further methylated by 20 y1 of dimethyl sulfate in 0.6 ml of 0.1 N NaOH. A reaction mixture was chromatographed on Whatman 3MM paper using solvent D. The band containing 5-Hydroxyuridine was extracted with water and the extract was further purified by paper chromatography in sol vent E. These procedures gave a 25% yield of mo5l). In addition to 5-Hydroxyuridine and the raw material, the methylated products contained 5% of 5-hydroxy-3-methyl uridine and 4% of 5-methoxy-3-methyluridine.