Synthesis of three hetero disaccharides, 4-O-beta-glucopyranosyl-6-deoxy-D-glucose, 4-O-beta-D-glucopyranosyl-D-mannosamine, and 4-O-beta-D-glucopyranosyl-D-mannose, and confirmation of their structures by C-13 NMR and MS.

The three disaccharides, 4-O-beta-D-glucopyranosyl-6-deoxy-D-glucose (Glc-6-deoxy-Glc), 4-O-beta-D-glucopyranosyl-D-mannosamine (Glc-ManN), 4-O-beta-D-glucopyranosyl-D-mannose (Glc-Man), were synthesized from equimolar amounts of 6-deoxy-glucose and alpha-D-glucose-1-phosphate (G-1-P), D-mannosamine and alpha-D-glucose-1-phosphate (G-1-P), and D-mannose and alpha-D-glucose-1-phosphate (G-1-P), respectively, using cellobiose phosphorylase from Cellvibrio gilvus. The yields were 60%, 10% and 50% based on the initial amounts of 6-deoxy-D-glucose, D-mannosamine and D-mannose, respectively. The structures of disaccharides were confirmed by NMR and mass spectroscopy analysis.