Glycoconjugates of amino acids.: Preparation through N-alkylation of amino acids with N-chloroacetyl-β-glycopyranosylamines

Monoalkylation of amino acids of different structural types with N-chloroacetylglycosylamines was shown to be applicable for the preparation of glycoconjugates containing beta-D-galactose, N-acetyl-beta-D-glucosamine, beta-D-mannose, and lactose residues. The glycoconjugates were synthesized from amino acids with secondary (sarcosine, L-proline) or primary (L-2- and 4-aminobutyric acids, L-tryptophan) amino groups as well as from various amino dicarboxylic acids (N-methyl-DL-aspartic, DL-aspartic, L-glutamic, and DL-2-aminoadipic acids). The derivatives obtained may be of interest for glycotargeting of physiologically active compounds of this series.