Nucleoside 5'-phosphordiamidates, synthesis and some properties.
A simple way of preparing nucleoside 5'-phosphordiamidate is described. The procedure is based on the ammonolysis of nucleoside 5'-phosphordichloridates by dilute aqueous ammonium hydroxide. The behaviour of nucleoside phosphordiamidates under acidic and alkaline conditions is also reported. Alkaline hydrolysis results in the formation of the parent nucleoside, whereas one amide group can be removed selectively by mild acid hydrolysis. This property of nucleoside phosphordiamidates served as a basis for the elaboration of a simple synthesis of nucleoside phosphoramidates starting from nucleosides.
D055598:Chemical Phenomena; D002621:Chemistry; D002713:Chlorine; D002855:Chromatography, Thin Layer; D004590:Electrophoresis, Paper; D006150:Guanine Nucleotides / Q000138:chemical synthesis; D006151:Guanosine; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D009711:Nucleotides / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds; D000644:Quaternary Ammonium Compounds; D013936:Thymidine; D013942:Thymine Nucleotides / Q000138:chemical synthesis*
D006150:Guanine Nucleotides; D009711:Nucleotides; D009943:Organophosphorus Compounds; D000644:Quaternary Ammonium Compounds; D013942:Thymine Nucleotides; C010755:nucleoside 5'-phosphordiamidates; D006151:Guanosine; D002713:Chlorine; D013936:Thymidine