N-Glycyl-beta-glycopyranosylamines, derivatives of mono- and disaccharides, and their use for the preparation of carboxylic acid glycoconjugates

A convenient preparative procedure was developed for the synthesis of N-gly cyl-beta-glycopyranosylamines. derivatives of monosaccharides (D-galactose, D-mannose, L-fucose, and N-acetyl-D-glucosamine) and disaccharides (lactos e, melibiose, cellobiose, and maltose). These compounds were demonstrated t o be useful for the preparation of glycoconjugates of biologically active c ompounds containing the carboxy group (nicotinic, orotic, kynurenic, and in doleacetic acids). Synthetic pathways were developed for conversions of N-g lycyl-beta-glycopyranosylamines into derivatives containing the carboxy gro up with the use of malonic and L-tartaric acid derivatives.