Abstract
Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the carbohydrate moiety of glycoprotein from Echinococcus granulosus have been accomplished. Trisaccharide Galβ1-3Galβ1-3GalNAcα1-R (A), tetrasaccharide Galα1-4Galβ1-3Galβ1-3GalNAcα1-R (B), and pentasaccharide Galα1-4Galβ1-3Galβ1-3Galβ1-3GalNAcα1-R (C), (R = biotinylated probe) were synthesized by stepwise condensation and/or block synthesis by the use of 5-(methoxycarbonyl)pentyl 2-azido-4,6-O-benzylidene-2-deoxy-α-d-galactopyranoside as a common glycosyl acceptor. The synthesis of the tetrasaccharide and the pentasaccharide was improved from the viewpoint of reducing the number of synthetic steps and increasing the total yield by changing from stepwise condensation to block synthesis. Moreover, hexasaccharide E, which contains the oligosaccharide sequence which occurs in E. granulosus, was synthesized from trisaccharide D. We examined the antigenicity of these five oligosaccharides by an enzyme-linked immunosorbent assay (ELISA). Although compounds of C–E did not exhibit antigenicity against cystic echinococcosis (CE) patient sera, compounds B, D, and E showed good serodiagnostic potential for alveolar echinococcosis (AE).
Highlights
In the course of our studies on natural oligosaccharides from invertebrate animal species, we are interested in the unique glycosphingolipids (GSLs) and glycoproteins (GPs) found in various Protostomia phyla and we have synthesized these oligosaccharides in order to elucidate biological functions [1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18]
E. multilocularis is a parasite, which belongs to the class Cestoda of the phylum Platyhelminthes and causes alveolar echinococcosis (AE), a severe parasitic zoonosis that can be fatal without appropriate treatment
A–E which carbohydrate structures that occur on the to study the surface of E. granulosus
Summary
In the course of our studies on natural oligosaccharides from invertebrate animal species, we are interested in the unique glycosphingolipids (GSLs) and glycoproteins (GPs) found in various Protostomia phyla and we have synthesized these oligosaccharides in order to elucidate biological functions [1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18]. Hülsmeier et al reported [20] in 2002 that Em2, an antigen extracted from E. multilocularis, is a mucin-type glycoprotein Based on this information, we synthesized four glycosphingolipids including Galβ1→6Galβ1-Cer as a core structure [15] and five carbohydrate. Based on this inforcore 1 of mucin-type O-glycans of E. multilocularis [8,11], and examined antigenicity of the mation, we synthesized four glycosphingolipids including Galβ1→6Galβ1-Cer as a core pure compounds by ELISA for their serodiagnostic potential [7,12,13]. The adult tode Echinococcus granulosus contains a novel mucin-type O-glycan capping motif consistworm lives in the small of a carnivore (definitive and the intermediate ing of Galpα1-4Gal linkages at intestine the non-reducing end (Figure 1). Compound D is isa synthetic a synthetic intermediate from the process ofcompound synthesizing compound E
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