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3'-Deoxycytidine

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3'-Deoxycytidine Basic information

Product Name:
3'-Deoxycytidine
Synonyms:
  • 3-DC
  • 3’-deoxy-cytidin
  • 3'-DEOXYCYTIDINE
  • 3'-deoxycytidine free base
  • 3'-Deoxy-D-cytidine
  • 3''-Deoxycytidine (and/or unspecified salts)
  • 1-(3-Deoxy-β-D-erythro-pentofuranosyl)cytosine
  • 4-amino-1-[(2R,3R,5S)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
CAS:
7057-33-2
MF:
C9H13N3O4
MW:
227.22
Mol File:
7057-33-2.mol
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3'-Deoxycytidine Chemical Properties

Melting point:
230-232 °C
Boiling point:
497.6±55.0 °C(Predicted)
Density 
1.73±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
pka
14.01±0.60(Predicted)
InChI
InChI=1S/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-6(14)3-5(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)/t5-,6+,8+/m0/s1
InChIKey
ZHHOTKZTEUZTHX-SHYZEUOFSA-N
SMILES
OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)C1
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Safety Information

RTECS 
HA3830000
HS Code 
29389090
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3'-Deoxycytidine Usage And Synthesis

Uses

3'-Deoxycytidine is an inhibitor of nucleolar RNA synthesis but does not affect the appearance of mRNA. Displayed inhibitory properties against the replication of hepatitis C virus-like RNA template.

Biological Activity

3'-Deoxycytidine is a pyrimidine analog of cordycepin. The structures of cordycepin and 3'-deoxycytidine resemble adenosine and cytidine except for the altered 3' position in the ribose moiety, where hydrogen is substituted for the hydroxyl group. 3'-deoxycytidine affects similar to that of cordycepin on nucleolar RNA formation and has approximately the same level of activity as the adenosine analog. 3'-deoxycytidine, like cordycepin, enters cells and is phosphorylated by the appropriate enzymes. 3'-Deoxycytidine shares with cordycepin the ability to inhibit nucleolar RNA synthesis, but it does not affect the appearance of mRNA. Neither compound affects heterogeneous nuclear RNA (HnRNA)[1].

References

[1] Herbert T. Abelson, Sheldon Penman. “Messenger RNA formation: Resistance to inhibition by 3′-deoxycytidine.” Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis 277 1 (1972): Pages 129-133.

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