ABSTRACT
Since glycosidase and glycosyltransferase inhibitors, composed of carba-sugars, have recently attracted much attention, it is desirable to develop effective preparative routes for provision of new carba-sugar derivatives of potential biological interest. 1,2:3,6-Dianhydro-5a-carba-alpha-glucopyranose was here chosen for study of synthetic utility, and demonstrated to be a promising intermediate for supplying several carba-beta-glycosylamines and N-linked dicarba-oligosaccharides. An N-linked 5a,5a'-dicarbalactose derivative obtained here was found to be a strong alpha-galactosidase inhibitor (IC50 1.2 microM, green coffee beans).
Subject(s)
Alkanes/chemistry , Amino Sugars/chemical synthesis , Disaccharides/chemical synthesis , Galactose/chemical synthesis , Glycoside Hydrolases/antagonists & inhibitors , Heterocyclic Compounds, 3-Ring/chemistry , Amino Sugars/chemistry , Disaccharides/chemistry , Galactose/chemistry , Glycoside Hydrolases/chemistryABSTRACT
Methyl 5a'-carba-beta-lactoside, imino-linked, has been shown to possess potent and specific inhibitory activity (IC50 = 185 microM) toward rat recombinant alpha2,3-sialyltransferase.