Synthesis and structural analysis of disaccharides of 4-O-β-d-glucopyranosyl-d-glucosamine and 4-O-d-β-glucopyranosyl-2-deoxy-d-glucose

The disaccharides 4-O-β-d-glucopyranosyl-d-glucosamine (Glc-GlcN) and 4-O-β-d-glucopyranosyl-2-deoxy-d-glucose (Glc-2-deoxy-Glc) were synthesized from equimolar amounts of d-glucosamine and α-d-glucose-1-phosphate (G-1-P), and 2-deoxy-d-glucose and α-d-glucose-1-phosphate (G-1-P) respectively, in the presence of cellobiose phosphorylase from Cellvibrio gilvus. The yields were 55% and 50% based on the initial amounts of d-glucosamine and 2-deoxy-d-glucose, respectively. The structure of disaccharides were confirmed by NMR analysis.