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2'-O-Methylcytidine

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2'-O-Methylcytidine Basic information

Product Name:
2'-O-Methylcytidine
Synonyms:
  • 2'-OMe-C
  • 4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-3-methoxy-5-methylol-tetrahydrofuran-2-yl]pyrimidin-2-one
  • 4-amino-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxyoxolan-2-yl]pyrimidin-2-one
  • 4-azanyl-1-[(2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxy-oxolan-2-yl]pyrimidin-2-one
  • 2'-OMe Cytidine
  • 4-aMino-1-[(2R,3R,4S,5R)-4-hydroxy-5-(hydroxyMethyl)-3-Methoxyoxolan-2-yl]-1,2-dihydropyriMidin-2-one
  • 2'-O-Methylcytidine, >98.0%(HPLC)
  • 2'-O-Methylcytidine, >=99%
CAS:
2140-72-9
MF:
C10H15N3O5
MW:
257.24
EINECS:
2017-001-1
Product Categories:
  • Bases & Related Reagents
  • Carbohydrates & Derivatives
  • Heterocycles
  • Nucleotides
  • Nucleosides, Nucleotides, Oligonucleotides
  • Biochemicals and Reagents
  • Nucleoside Analogs
  • Nucleosides
  • Modified（deoxy）nucleoside
  • Nucleosides-2'-OMe Nucleosides
Mol File:
2140-72-9.mol
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2'-O-Methylcytidine Chemical Properties

Melting point:
252-253 C
Boiling point:
506.0±60.0 °C(Predicted)
Density 
1.68±0.1 g/cm3(Predicted)
storage temp. 
Keep in dark place,Sealed in dry,Store in freezer, under -20°C
solubility 
Soluble in DMSO.
pka
13.37±0.70(Predicted)
form 
Powder
color 
White to Off-white
PH
4.2
optical activity
70.902° (C=0.01 g/ml, H2O)
λmax
281 (pH 1)；273 (EtOH)
InChI
InChI=1S/C10H15N3O5/c1-17-8-7(15)5(4-14)18-9(8)13-3-2-6(11)12-10(13)16/h2-3,5,7-9,14-15H,4H2,1H3,(H2,11,12,16)/t5-,7-,8-,9-/m1/s1
InChIKey
RFCQJGFZUQFYRF-ZOQUXTDFSA-N
SMILES
OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](OC)[C@@H]1O
CAS DataBase Reference
2140-72-9(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-24/25
WGK Germany 
3
HS Code 
29349990

MSDS

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2'-O-Methylcytidine Usage And Synthesis

Description

2'-O-Methylcytidine is a nucleoside with a hydroxyl group on the 2' carbon, making it an effective viral replication inhibitor. 2'-O-Methylcytidine is also metabolized by nucleotide salvage pathways and may be able to bind to the response element on DNA, which could inhibit protein synthesis in cancer cells. It is an inhibitor of hepatitis C virus (HCV) non-structural protein 5B (NS5B; IC50 = 3.8 μM). It inhibits HCV replication in a replicon assay (IC50 = 21.2 μM).

Chemical Properties

White powder

Uses

2'-O-Methylcytidine is used in the preparation of nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase.

Uses

Cytidine analog.

Definition

ChEBI: 2'-O-methylcytidine is a methylcytidine.

References

[1] GIOVANNI MIGLIACCIO. Characterization of resistance to non-obligate chain-terminating ribonucleoside analogs that inhibit hepatitis C virus replication in vitro.[J]. The Journal of Biological Chemistry, 2003, 278 49: 49164-49170. DOI: 10.1074/jbc.m305041200

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