| Identification | More | [Name]
2'-O-Methyluridine | [CAS]
2140-76-3 | [Synonyms]
2'-O-METHYLURIDINE
2'-O-METHYLURIDINE (CHIRAL)
2''-O-METHYLURIDINE CRYSTALLINE | [EINECS(EC#)]
2017-001-1 | [Molecular Formula]
C10H14N2O6 | [MDL Number]
MFCD00056054 | [Molecular Weight]
258.23 | [MOL File]
2140-76-3.mol |
| Questions And Answer | Back Directory | [Synthesis]
Under a nitrogen atmosphere, 10% palladium solid on carbon was added to a BOM-protected uridine derivative (1 equivalent) in a mixed solution of isopropanol and water (10:1 ratio). HCO2H (0.5%) was then added to the reaction system. Hydrogen gas was introduced into the reaction mixture using a double-folded balloon. After the reaction was complete, the palladium solid on carbon was removed by diatomaceous earth filtration, and the reaction mixture was washed with isopropanol. All volatiles were rotary evaporated under vacuum to generate the HCO2H-amine salt. The crude mixture was then dissolved in chloroform and washed with an aqueous sodium bicarbonate solution. The combined organic layers were dried with anhydrous sodium sulfate, and the combined organic extracts were evaporated under vacuum. The residue was purified by silica gel chromatography to obtain the target product, 2'-methoxyuridine. 
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| Chemical Properties | Back Directory | [Melting point ]
154-156°C | [density ]
1.53±0.1 g/cm3(Predicted) | [storage temp. ]
Store at 0°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Powder | [pka]
9.39±0.10(Predicted) | [color ]
White to Off-white | [PH]
～9.3 | [λmax]
261nm(MeOH)(lit.) | [InChI]
InChI=1S/C10H14N2O6/c1-17-8-7(15)5(4-13)18-9(8)12-3-2-6(14)11-10(12)16/h2-3,5,7-9,13,15H,4H2,1H3,(H,11,14,16)/t5-,7-,8-,9-/m1/s1 | [InChIKey]
SXUXMRMBWZCMEN-ZOQUXTDFSA-N | [SMILES]
OC[C@H]1O[C@@H](N2C=CC(=O)NC2=O)[C@H](OC)[C@@H]1O | [CAS DataBase Reference]
2140-76-3(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
2'-O-Methyluridine is an analog of uridine and has been shown to have antiviral and anticancer properties. 2'-O-Methyluridine inhibits protein synthesis by competing with uridine for the active site of the enzyme ribonucleotide reductase, which converts ribonucleotides to dNMPs. This compound also inhibits RNA synthesis by disrupting the pairing of adenine and cytosine residues in RNA strands. | [Chemical Properties]
White Solid | [Uses]
Uridine analog. 2'-O-Methyluridine is used for preparation of antiviral nucleoside derivatives as inhibitors of subgenomic hepatitis C virus RNA replication.
| [Definition]
ChEBI: A methyluridine that consists of uridine bearing a single methyl substituent located at position O-2' on the ribose ring. | [Source]
2'-O-Methyluridine is found in rRNA, snRNA, snoRNA and tRNA of Archaea, Bacteria, and Eukaryota[1].
| [References]
[1] Agota Au?ynait?. “Identification of a 2’-O-Methyluridine Nucleoside Hydrolase Using the Metagenomic Libraries.” Molecules 23 11 (2018).
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