Synthesis and biological activities of methyl oligobiosaminide and some deoxy isomers thereof.
Methyl oligobiosaminide (1) the core structure of oligostatin C, and five analogues, the 6-hydroxy-(2), 2-deoxy- (3), 2-deoxy-6-hydroxy- (4), 3-deoxy- (5), and 3-deoxy-6-hydroxy derivatives (6), were synthesized by coupling the protected pseudo-sugar epoxide 46 with suitable methyl 4-amino-4-deoxy-alpha-D-hexopyranoside derivatives. Compounds 3 and 6 showed notable inhibitory activity against alpha-D-glucosidase and alpha-D-mannosidase, respectively, whereas compound 1 had almost no activity.
Shibata
Y
Y
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan.
Kosuge
Y
Y
Ogawa
S
S
D002240:Carbohydrate Sequence; D055598:Chemical Phenomena; D002621:Chemistry; D004187:Disaccharides; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D008361:Mannosidases / Q000037:antagonists & inhibitors; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000494:pharmacology; D015003:Yeasts / Q000201:enzymology; D001617:beta-Glucosidase / Q000037:antagonists & inhibitors
D004187:Disaccharides; D009844:Oligosaccharides; C064839:methyl oligobiosaminide; D008361:Mannosidases; D001617:beta-Glucosidase