title: Synthetic studies on glycosphingolipids from protostomia phyla: synthesis of glycosphingolipids and related carbohydrate moieties from the parasite Schistosoma mansoni.
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.
authors.affiliation: Faculty of Pharmacy, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan.
authors.forename: Takayuki
authors.initials: T
authors.lastname: Kanaya
authors.forename: Frank
authors.initials: F
authors.lastname: Schweizer
authors.forename: Tadahiro
authors.initials: T
authors.lastname: Takeda
authors.forename: Fumiyuki
authors.initials: F
authors.lastname: Kiuchi
authors.forename: Noriyasu
authors.initials: N
authors.lastname: Hada
mesh_terms: D000818:Animals; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D006028:Glycosphingolipids / Q000138:chemical synthesis* / Q000737:chemistry; D008969:Molecular Sequence Data; D012550:Schistosoma mansoni / Q000737:chemistry*
chemical_list: D002241:Carbohydrates; D006028:Glycosphingolipids