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.
Tariq
M A
MA
National Food Research Institute, Ibaraki, Japan.
Hayashi
K
K
D000606:Amino Sugars / Q000138:chemical synthesis / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D005964:Glucosyltransferases / Q000378:metabolism; D006088:Gram-Negative Aerobic Bacteria / Q000201:enzymology; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008320:Maltose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D013058:Mass Spectrometry / Q000379:methods; D008969:Molecular Sequence Data; D013329:Structure-Activity Relationship
C095556:4-O-glucopyranosyl-6-deoxyglucose; C095557:4-O-glucopyranosylmannosamine; D000606:Amino Sugars; D004187:Disaccharides; D007202:Indicators and Reagents; C095558:4-glucopyranosylmannose; D008320:Maltose; D005964:Glucosyltransferases; C034714:cellobiose phosphorylase