2’-Deoxy-2’-fluoroguanosine - CAS 78842-13-4
Category:
Nucleosides
Product Name:
2’-Deoxy-2’-fluoroguanosine
Catalog Number:
78842-13-4
CAS Number:
78842-13-4
Molecular Weight:
285.23
Molecular Formula:
C10H12FN5O4
COA:
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MSDS:
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Structure\Application:
2'-Deoxy-Nucleosides
Chemical Structure
CAS 78842-13-4 2’-Deoxy-2’-fluoroguanosine

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Reference Reading


1.Synthesis of 2'-deoxy-2'-fluoroguanyl-(3',5')-guanosine.
Maruyama T1, Kozai S, Nakamura K, Irie M. Nucleosides Nucleotides Nucleic Acids. 2002 Nov-Dec;21(11-12):765-74.
The protected analogue of 2-amnio-6-chloropurine arabinoside (3b) was subjected to reaction with diethylaminosulfur trifluoride (DAST) and subsequently treated with NaOAc in Ac2O/AcOH to give N2, O3', O5'-triacetyl-2'-deoxy-2'-fluoroguanosine (5a). After deacetylation of the sugar moiety and protection of 5'-OH by a 4,4'-dimethoxytrityl group, this nucleoside component was converted to 2'-deoxy-2'-fluoroguanyl-(3',5')-guanosine (6c, GfpG).
2.Chemical and enzymatic synthesis and antiviral properties of 2'-deoxy-2'-fluoroguanosine.
Zaitseva GV1, Zinchenko AI, Barai VN, Pavlova NI, Boreko EI, Mikhailopulo IA. Nucleosides Nucleotides. 1999 Apr-May;18(4-5):687-8.
Chemical and enzymatic methods were employed for the synthesis of the title compound, 2'F-Guo 7. High antiviral activity of 2'F-Guo was established in chick embryo cells infected with influenza virus FPV/Rostock/34 (H7N1) and herpes simplex virus (HSV) type I (1C strain).
3.Crystal structure of RNase T1(Y45W) complexed with 3'AMP and GflpA.
Gohda K1, Itoh T, Hiramatsu Y, Tomita K, Nishikawa S, Uesugi S, Morioka H, Ohtsuka E, Ikehara M, Hakoshima T. J Biochem. 1993 Dec;114(6):842-8.
We have previously reported the crystallization of a mutant RNase T1(Y45W) with a synthetic modified trinucleotide ApGflpA [Hakoshima, T. et al. (1990) J. Biochem. 108, 695-698]. In the present report, we describe the crystal structure refined at 2.4 A resolution. During the refinement process, we found that the ApGflpA molecule was cleaved at the phosphodiester bond between the 5'-terminal adenosine and the subsequent 2'-fluoroguanosine. At the end of the refinement (R = 17.1%), it was supposed that the resulting molecules, i.e., 3'AMP and GflpA, were separately bound to the enzyme. In the complex structure, the binding-site of the enzyme was occupied by the guanine base of GflpA via a similar interaction to that of the enzyme complexed with 2'GMP, while the phosphate group of GflpA was not bound to the active site. The guanosine adopted the anti orientation on the glycosyl torsion angle with a C2'-endo-C3'-exo sugar pucker. This conformation resulted in the phosphate group protruding from the active site.
4.[Antiviral activity of 2'-deoxy-2'-fluoroguanosine against influenza and herpes simplex viruses in cultured cells].
Boreko I, Pavlova NI, Zaĭtseva GV, Mikhaĭlopulo IA. Vopr Virusol. 2001 Sep-Oct;46(5):40-2.
High antiviral activity of 2'-deoxy-2'fluoroguanosine (2'-D-2'-FG) was observed in chicken embryo cells infected with FPV/Rostock/34 (H7N1) influenza virus and herpes simplex virus (HSV) type I (strain 1C). 50% inhibitory concentration (IC50) of 2'-D-2'-FG was 1.44 microM for FPV and 0.093 microM for HSV. IC50 of remantadine hydrochloride, ribavirin (FPV), and acycloguanosine (HSV) were < 0.46, 14.4, and 0.08 microM, respectively. Anti-HSV activity was confirmed in Vero cells: IC50 < 0.34 microM for 2'-D-2'-FG and IC50 < 0.044 microM for acycloguanosine.