Efficient Preparation of Aminoxyacyl Amides, Aminoxy Hybrid Peptides, and alpha-Aminoxy Peptides

Abstract

N-(Pg-alpha-aminoxy acids) 1a-g are converted to N-(Pg-alpha-aminoxyacyl)benzotriazoles 2a-g, Which react under mild conditions with amines, alpha-amino acids/alpha-dipeptides, and alpha-aminoxy acids to give aminoxyacyl amides 3a-g, (3e + 3e'), and (3g + 3g'), aminoxy hybrid peptides 4a-h, (4a + 4a'), 6a-d, 9a-c, (9a + 9a'), and (9b + 9b'), and a-aminoxy peptides 10a,b in good yields without racemization.