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| | 2'-Deoxy-2'-fluoroguanosine Basic information |
| | 2'-Deoxy-2'-fluoroguanosine Chemical Properties |
| Melting point | 262-264 °C(Solv: water (7732-18-5)) | | density | 2.17±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C(protect from light) | | solubility | DMSO : 50 mg/mL (175.30 mM) | | pka | 9?+-.0.20(Predicted) | | form | Powder | | color | White to Off-white | | InChI | InChI=1S/C10H12FN5O4/c11-4-6(18)3(1-17)20-9(4)16-2-13-5-7(16)14-10(12)15-8(5)19/h2-4,6,9,17-18H,1H2,(H3,12,14,15,19)/t3-,4-,6-,9-/m1/s1 | | InChIKey | UXUZARPLRQRNNX-DXTOWSMRSA-N | | SMILES | OC[C@H]1O[C@@H](N2C3=C(C(NC(=N3)N)=O)N=C2)[C@H](F)[C@@H]1O |
| | 2'-Deoxy-2'-fluoroguanosine Usage And Synthesis |
| Uses | 2''-Deoxy-2''-fluoroguanosine, can be used as powerful tool for structural manipulation of G-quadruplexes. It is also a influenza viral polymerase inhibitor like Ribavirin (R414475), used as a antiviral drug against avian (H5N1) influenza virus. | | Definition | 2'-Deoxy-2'-fluoroguanosine is an analog of guanosine that inhibits the viral life cycle. It is a competitive inhibitor of the viral transcriptase enzyme, which prevents RNA synthesis and subsequent protein synthesis. 2'-Deoxy-2'-fluoroguanosine has been shown to inhibit the growth of wild-type viruses in cell culture and to be effective against resistant mutants in cell culture. This drug has also been shown to inhibit the replication of herpes simplex virus type 1 (HSV-1) and influenza virus type A/WSN/33 (H1N1) in cell culture, as well as inhibiting the production of rna from these viruses. | | Synthesis | The synthesis of 2'-deoxy-2'-fluoroguanosine was accomplished using tetraisopropyldisiloxanyl (TPDS) protected 9-beta-D-arabinofuranosylguanine as starting material, and conversion to the intermediate diisobutyryl-arabinofuranosylguanosine. Deprotection of the TPDS group, was followed by protection of the hydroxyl group with THP to give diisobutyryl di-THP protected arabinofuranosylguanine. Selective O-deacylation and triflation was followed by treatment of the crude product with fluoride, then deprotection of the THP groups. | | References | [1] M. Ikehara, J. Imura. “Studies on Nucleosides and Nucleotides. LXXXVII. Purine Cyclonucleosides. XLII. Synthesis of 2’-Deoxy-2’-fluoroguanosine.” Chemical & pharmaceutical bulletin 22 1 (1981): 1034–1038.
[2] G V Zaitseva. “Chemical and enzymatic synthesis and antiviral properties of 2’-deoxy-2’-fluoroguanosine.” Nucleosides & nucleotides 18 4–5 (1999): 687–8.
[3] M Tisdale. “Inhibition of influenza virus transcription by 2’-deoxy-2’-fluoroguanosine.” Antimicrobial Agents and Chemotherapy 39 11 (1995): 2454–8. |
| | 2'-Deoxy-2'-fluoroguanosine Preparation Products And Raw materials |
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