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CS-W001157 4
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3'-Deoxy-3'-fluoroadenosine

  • CAS No. 75059-22-2

  • Cat. No. CS-0022620
  • Purity≥98%
  • MDL No.MFCD20134043

*For research and further manufacturing use only, not for direct human use.

3'-Deoxy-3'-fluoroadenosine|CS-0022620

Structure of 75059-22-2

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General Information

  • CAS No. 75059-22-2
  • Cat. No. CS-0022620
  • Purity ≥98%
  • MDL No. MFCD20134043
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₂FN₅O₃
  • Molecular Weight 269.24
  • Synonym(s) None
  • SMILES OC[C@H]1O[C@@H](N(C=N2)C3=C2C(N)=NC=N3)[C@H](O)[C@@H]1F

Description

3'-Deoxy-3'-fluoroadenosine features a fluorine atom at the 3' position, replacing the hydroxyl group to enhance metabolic stability. This modification impedes phosphorylation and prevents chain elongation, making it a potent inhibitor of viral polymerases. The compound integrates into nucleic acid chains during replication, halting further extension due to the absence of a 3'-OH. Its electron-withdrawing fluorine substituent increases resistance to enzymatic degradation. Used in antiviral research, particularly against retroviruses and hepatitis B.

Application

3'-Deoxy-3'-fluoroadenosine serves as a valuable nucleoside analog for probing ribose conformation and enzyme substrate specificity in antiviral and anticancer research. Its 3'-fluoro substitution confers enhanced metabolic stability while maintaining compatibility with standard phosphorylation pathways, enabling direct incorporation into oligonucleotide synthesis workflows. The compound functions as a key building block for site-specific modification of RNA analogs and supports efficient coupling reactions under mild conditions.

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H332-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   119.31
  • LogP   -1.0028
  • H_Acceptors   8
  • H_Donors   3
  • Rotatable_Bonds   2

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