α-Aminoacyl derivatives of aminobenzoic acid and of amino-oxy-acids by reaction of their hydrochlorides with amino-acid N-carboxyanhydrides

Abstract

The reaction of amino-acid N-carboxyanhydrides with hydrochlorides of aminobenzoic acids and of amino-oxy-acids gave amino-acid amides in a one-step synthesis. The coupling of L-alanine N-carboxyanhydride with anthranilic and with p-aminobenzoic acid hydrochloride gave peptide-like compounds of high optical activity, indicating the presence of little or no racemate. Glycyl and DL-phenylalanyl amides with aminobenzoic acid were obtained in this way, and trimers were formed by reaction of the N-carboxyanhydrides with p-aminobenzoyl-L-glutamic acid hydrochloride.

Parallel procedures led to the α-, β-, and γ-amido-oxy-peptides of amino-oxy-acetic, -propionic, and -butyric acid, respectively.