Synthesis of new N-containing maltooligosaccharides, alpha-amylase inhibitors, and their biological activities

Fifteen new N-containing maltooligosaccharides were obtained using the chem oenzymatic method. Among these compounds, maltooligosaccharides having 6-am ino-6-deoxy-D-sorbitol residue, (3R, 4R, 5R, 6S)-hexahydro-3,4,5,6-tetrahyd roxy-1H-azepine residue, and (3R,5R)-3,4,5-trihydroxypiperidine residue at the reducing end showed strong inhibitory activities for human pancreatic a lpha-amylase (HPA) (EC 3.2.1.1) and human salivary alpha-amylase (HSA). The administration of (3R,4R,5R,6S)-hexahydro-3,5,6-trihydroxy-1H-azepine-4-yl O-alpha-D-glucopyranosyl-(1-->4)-alpha-D-glycopyranoside (13, IC50 = 4.3 x 10(-5) M for HPA, IC50 = 8.2 x 10(-5) M for HSA) and (3R,5R)-3,5-dihydroxy piperidine-4-yl O-alpha-D-glucopyranosyl-(1-->4)-alpha-D-glucopyranoside (1 8, IC50 = 3.4 x 10(-5) M for HPA, IC50 = 4.6 x 10(-5) M for HSA) to ICR mic e suppressed postprandial hyperglycemia.