A novel two-step synthesis of alpha-linked mannobioses based on an acid-assisted reverse hydrolysis reaction

作者：Ajisaka Katsumi^*; Yagura Misato; Miyazaki Tatsuo

来源：Carbohydrate Research, 2012, 347(1): 147-150.

DOI：10.1016/j.carres.2011.10.037

• Mannobiose
• Acid-assisted reverse hydrolysis reaction
• Fischer glycosylation
• Acid catalyst

Instead of an enzyme-assisted reverse hydrolysis reaction for the synthesis of manno-oligosaccharides, we propose here a versatile new approach. By Fischer type glycosylation, a D-mannose solution of extremely high concentration (approximately 83% (w/w)) was incubated at 60 degrees C for 65 h in 0.5 M HCl. After dilution and neutralization, the small amount of formed beta-linked oligosaccharides was hydrolyzed by beta-mannosidase. The yields of alpha-D-Manp-(1 -%26gt; 2)-D-Manp (7.9%), alpha-D-Manp-(1 -%26gt; 3)-D-Manp (7.9%), and alpha-D-Manp-(1 -%26gt; 6)-D-Manp (29.1%) isolated by an activated carbon column chromatography were almost identical to those of the enzymatic reaction, but the yield of alpha-D-Manp-(1 -%26gt; 3)-D-Manp increased enormously by the present method.

• 出版日期2012-1-10