Synthesis of N-phosphoryl amino acids via phosphoramidite amine-exchange

Article abstract of DOI:10.1016/S0040-4039(98)01673-6

N-Phosphoryl amino acids were prepared rapidly and in high yield via phosphoramidite amine-exchange in the presence of 1H-tetrazole followed by oxidation with mCPBA. Formation of dibenzyl phosphoramidates incorporating the representative C-terminal protected amino acids leucine, phenylalanine, glutamic acid, and proline were demonstrated to be most successful with dibenzyl N,N-dimethylphosphoramidite although the N,N-diethyl and N,N- diisopropyl analogs also provided high yields.