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

Abstract

N-Phosphoryl amino acids were prepared rapidly and in high yield via phosphoramidite amine-exchange in the presence of 1 H-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.