A new route to oligodeoxynucleoside phosphoramidates (P-NH2)

Article abstract of DOI:10.1016/S0040-4039(97)01153-2

We describe a new strategy to introduce phosphoramidate (P-NH₂) internucleosidic linkages in oligonucleoside phosphodiesters using dimer building blocks. The P-NH₂ function is generated under photolysis of the N-2-nitrobenzylphosphoramidate linkage (P-NHR). We achieved the synthesis of N-2-nitrobenzylphosphoramidate β and α-anomeric nucleotides dimers via either phosphoramidite or H-phosphonate chemistry, α-dimer (P-NHR) was incorporated at defined positions into α-oligonucleoside phosphodiesters and the P-NH₂ linkage was liberated by U.V irradiation.