3469-78-1

Basic information

• Product Name: Adenosine 5-monophosphate, monoanhydride with (phosphonomethyl)phosphonic acid
• Synonyms: β,γ-methylene ATP;β,γ-methylene-ATP;adenosine-5’-[(β,γ)-methyleno]triphosphate;AMP-PCP;beta,gamma-methylene-ATP;β,γ-meATP
• CAS NO: 3469-78-1
• Molecular Formula: C₁₁H₁₈N₅O₁₂P₃
• Molecular Weight: 505.212
• Mol File: 3469-78-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Adenosine 5-monophosphate, monoanhydride with (phosphonomethyl)phosphonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Adenosine 5-monophosphate, monoanhydride with (phosphonomethyl)phosphonic acid(3469-78-1)
• EPA Substance Registry System: Adenosine 5-monophosphate, monoanhydride with (phosphonomethyl)phosphonic acid(3469-78-1)

Safety Data

• Hazardous Substances Data: 3469-78-1(Hazardous Substances Data)

Upstream product

• 1984-15-2 Methylenediphosphonic acid 
• 61-19-8 5'-adenosine monophosphate 
• 43171-39-7 methylenediphosphonate tris-tributylammonium salt 
• 7331-13-7 adenosine 5'-monophosphate morpholidate 

Relevant articles and documents

Synthesis and properties of novel NTP derivatives

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

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.

4-nitrophenyl 4-morpholinylphosphonochloridate: a convenient reagent for the synthesis of ribonucleoside mono-, di- and tri-phosphates

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.