title: Synthetic studies on glycosphingolipids from the Protostomia phyla: syntheses of arthro-series glycosphingolipids.
abstract: Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar, have quite unique structures containing GlcNAcbeta-(1 --> 3)-Man and GalNAcbeta-(1 --> 4)-GlcNAcbeta-(1 --> 3)-Man. We have synthesized two glycosphingolipids, beta-D-GlcNAcp-(1 --> 3)-beta-D-Manp-(1 --> 4)-beta-D-Glcp-(1 --> 1)-Cer and beta-D-GalNAcp-(1 --> 4)-beta-D-GlcNAcp-(1 --> 3)-beta-D-Manp-(1 --> 4)-beta-D-Glcp-(1 --> 1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the beta-mannopyranosidic linkages.
authors.affiliation: Kyoritsu College of Pharmacy, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan.
authors.forename: Isao
authors.initials: I
authors.lastname: Ohtsuka
authors.forename: Noriyasu
authors.initials: N
authors.lastname: Hada
authors.forename: Mutsumi
authors.initials: M
authors.lastname: Sugita
authors.forename: Tadahiro
authors.initials: T
authors.lastname: Takeda
mesh_terms: D000818:Animals; D017165:Ascaris suum / Q000737:chemistry*; D005643:Fucose; D006028:Glycosphingolipids / Q000138:chemical synthesis*; D007448:Invertebrates / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose; D009005:Monosaccharides / Q000138:chemical synthesis; D009844:Oligosaccharides / Q000138:chemical synthesis
chemical_list: D006028:Glycosphingolipids; D009005:Monosaccharides; D009844:Oligosaccharides; D005643:Fucose; D008358:Mannose