Synthesis of new aminoacyl-adenylate analogs having an N-acyl phosphoramidate linkage

Article abstract of DOI:10.1016/S0040-4039(98)00570-X

New aminoacyl-adenylate analogs (aa-AMPNs), in which the oxygen atom of the mixed anhydride bond of aminoacyl-adenylates is replaced by an NH group, were synthesized by the reaction of an adenosine 5'-phosphoramidite derivative with appropriately protected amino acid amides. Among various reagents studied for activation of the 5'-phosphoramidite derivative, 5-(4- nitrophenyl)-1H-tetrazole was found to give N-acyl phosphoramidate derivatives in good yields.