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  • Title: Synthetic studies on glycosphingolipids from protostomia phyla: synthesis of glycosphingolipids and related carbohydrate moieties from the parasite Schistosoma mansoni.
    Author: Kanaya T, Schweizer F, Takeda T, Kiuchi F, Hada N.
    Journal: Carbohydr Res; 2012 Nov 01; 361():55-72. PubMed ID: 22982172.
    Abstract:
    Stereocontrolled syntheses of three neutral glycosphingolipids and six oligosaccharide derivatives found from the parasite Schistosoma mansoni have been accomplished. A pentasaccharide glycosphingolipid β-D-Galp-(1→4)-[α-L-Fucp-(1→3)]-β-D-GlcpNAc-(1→3)-β-D-GalpNAc-(1→4)-β-D-Glcp-(1↔1)-Cer (1), two hexasaccharide glycosphingolipids α-L-Fucp-(1→3)-β-D-Galp-(1→4)-[α-L-Fucp-(1→3)]-β-D-GlcpNAc-(1→3)-β-D-GalpNAc-(1→4)-β-D-Glcp-(1↔1)-Cer (2) and β-D-Galp-(1→4)-[α-L-Fucp-(1→3)]-β-D-GlcpNAc-(1→3)-β-D-GlcpNAc-(1→3)-β-D-GalpNAc-(1→4)-β-D-Glcp-(1↔1)-Cer (3), together with their non-reducing end tri- and tetrasaccharides, β-D-Galp-(1→4)-[α-L-Fucp-(1→3)]-β-D-GlcpNAcOR (4) and α-L-Fucp-(1→3)-β-D-Galp-(1→4)-[α-L-Fucp-(1→3)]-β-D-GlcpNAcOR (5), were synthesized by block synthesis. Moreover, non-reducing end oligosaccharides of schistosomal glycosphingolipids, β-D-GalpNAc-(1→4)-[α-L-Fucp-(1→3)]-β-D-GlcpNAcOR (6), α-L-Fucp-(1→3)-β-D-GalpNAc-(1→4)-[α-L-Fucp-(1→3)]-β-D-GlcpNAcOR (7), α-L-Fucp-(1→3)-β-D-GalpNAc-(1→4)-[α-L-Fucp-(1→2)-α-L-Fucp-(1→3)]-β-D-GlcpNAcOR (8) and α-L-Fucp-(1→3)-β-D-GalpNAc-(1→4)-[α-L-Fucp-(1→2)-α-L-Fucp-(1→2)-α-L-Fucp-(1→3)]-β-D-GlcpNAcOR (9) [R=2-(trimethylsilyl)ethyl], were synthesized as probes to explore their diagnostic potential to detect schistosomiasis from patients' sera.
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