Optical resolution of amino acid derivatives by high-performance liquid chromatography on tris(phenylcarbamate)s of cellulose and amylose

Abstract

The optical resolution of ten N-protected alanine esters was examined by high-performance liquid chromatography using six cellulose and five amylose tris(phenylcarbamate) derivatives as chiral stationary phases. Tris(3,5-dimethylphenylcarbamate)s of both cellulose and amylose showed high resolving power for these racemates. The resolution of 23 N-benzyloxycarbonyl α-amino acid esters was also tested on tris(3,5-dimethylphenylcarbamate)s of cellulose and amylose. All amino acid derivatives except two were completely resolved at least by one of the colums. On cellulose tris(3,5-dimethylphenylcarbamate), thel-isomers of the amino acids except for threonine were eluted first.