3469-78-1Relevant academic research and scientific papers
Synthesis and properties of novel NTP derivatives
Padyukova,Dixon,Efimtseva,Ermolinsky,Mikhailov,Karpeisky
, p. 1013 - 1014 (1999)
Simple method for the preparation of anhydrides of nucleoside-5'- monophosphoric acid and with 1-hydroxyethane-1,1-diylbis(phosphonic acid) has been developed.
Solid-phase synthesis of 5′-O-β,γ-methylenetriphosphate derivatives of nucleosides and evaluation of their inhibitory activity against HIV-1 reverse transcriptase
Ahmadibeni, Yousef,Dash, Chandravanu,Le Grice, Stuart F.J.,Parang, Keykavous
, p. 3010 - 3013 (2010)
Bis(dichlorophosphino)methane was converted to a β,γ-methylenetriphosphitylating reagent. The reagent was immobilized on aminomethyl polystyrene resin-bound linker of 4-acetoxy-3-phenylbenzyl alcohol to afford a polymer-bound β,γ-methylenetriphosphitylating reagent, which was reacted with unprotected nucleosides followed by oxidation with tert-butyl hydroperoxide, deprotection of cyanoethoxy groups with DBU, and acidic cleavage to produce 5′-O-β,γ-methylene triphosphate nucleosides in 53-82% overall yields. Among all the compounds, cytidine 5′-O-β,γ-methylenetriphosphate inhibited completely RNase H activity of HIV-1 reverse transcriptase at 700 μM.
5′-β,γ-CHF-ATP Diastereomers: Synthesis and Fluorine-Mediated Selective Binding by c-Src Protein Kinase
Hwang, Candy S.,Kung, Alvin,Kashemirov, Boris A.,Zhang, Chao,McKenna, Charles E.
supporting information, p. 1624 - 1627 (2015/04/14)
The first preparation of the individual β,γ-CHF-ATP stereoisomers 12a and 12b is reported. Configurationally differing solely by the orientation of the C-F fluorine, 12a and 12b have discrete 31P (202 MHz, pH 10.9, ΔδPα 6 Hz, ΔδPβ 4 Hz) and 19F NMR (470 MHz, pH 9.8, ΔδF 25 Hz) spectral signatures and exhibit a 6-fold difference in IC50 values for c-Src kinase, attributed to a unique interaction of the (S)-fluorine of bound 12b with R388 in the active site.
4-nitrophenyl 4-morpholinylphosphonochloridate: a convenient reagent for the synthesis of ribonucleoside mono-, di- and tri-phosphates
Hartog, J. A. J. den,Boom, J. H. van
, p. 285 - 290 (2007/10/02)
The synthesis of the crystalline and easily accessible phosphorylating agent 4-nitrophenyl 7-morpholinylphosphonochloridate is reported.Its application to the preparation of 5'-phosphorylated ribonucleosides (e.g. pA, ppA and pppA) as well as RNA fragments (e.g. pUpU and ppUpU) is demonstrated.Further, special attention is paid to the mild removal of the 4-nitrophenyl group from fully protected phosphotriester intermediates.
