Synthesis of aminoacyl derivatives of sugars

Abstract

A simple and convenient method for preparation of aminoacyl derivatives of simple sugars by the condensation of unprotected carbohydrate with N-carbobenzoxyaminoacid in the presence of carbodiimide has been developed. The condensation of glucose with N-carbobenzoxyaminoacid affords almost exclusively the 6-O (N-carbobenzoxyaminoacyl)-sugars. By this method 6-O (N-carbobenzoxyaminoacyl)- d-glucoses containing residues of glycine, d, l-alanine, d, l-valine, d, l-norleucine, β-alanine and ϵ-aminocaproic acid have been prepared. The unprotected aminosugars condense smoothly with N-carbobenzoxyaminoacid in the presence of carbodiimide in aqueous pyridine to form N-(N′-carbobenzoxyaminoacyl)-hexosamine. The N-carbobenzoxy derivatives were converted to O- and N-aminoacyl derivatives with free amino groups by hydrogenolysis in aqueous methanol in the presence of oxalic acid. Corresponding O- and N-aminoacyl derivatives have been isolated as oxalates.