title: Synthesis of the conjugation ready, downstream disaccharide fragment of the O-PS of Vibrio cholerae O:139.
abstract: The linker-equipped disaccharide, 8-amino-3,6-dioxaoctyl 2,6-dideoxy-2-acetamido-3-O-β-D-galactopyranosyluronate-β-D-glucopyranoside (10), was synthesized in eight steps from acetobromogalactose and ethyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-1-thio-β-D-glucopyranoside. The hydroxyl group present at C-4(II) in the last intermediate, 8-azido-3,6-dioxaoctyl 4-O-benzyl-6-bromo-2,6-dideoxy-2-trichloroacetamido-3-O-(benzyl 2,3-di-O-benzyl-β-D-galactopyranosyluronate)-β-D-glucopyranoside (9), is positioned to allow further build-up of the molecule and, eventually, construction of the complete hexasaccharide. Global deprotection (9→10) was done in one step by catalytic hydrogenolysis over palladium-on-charcoal.
authors.affiliation: NIDDK, LBC, National Institutes of Health, Bethesda, MD 20892-0815, USA.
authors.forename: Shujie
authors.initials: S
authors.lastname: Hou
authors.forename: Pavol
authors.initials: P
authors.lastname: Kováč
mesh_terms: D000906:Antibodies / Q000276:immunology / Q000378:metabolism; D000942:Antigens, Bacterial / Q000737:chemistry* / Q000276:immunology; D002236:Carbohydrate Conformation; D002771:Cholera / Q000276:immunology / Q000378:metabolism / Q000382:microbiology*; D004187:Disaccharides / Q000138:chemical synthesis* / Q000276:immunology; D018604:Epitope Mapping / Q000379:methods; D006001:Glycoconjugates / Q000138:chemical synthesis / Q000276:immunology; D006801:Humans; D018796:Immunoconjugates / Q000737:chemistry / Q000276:immunology; D018716:Molecular Mimicry / Q000276:immunology; D011485:Protein Binding; D041242:Vibrio cholerae O139 / Q000737:chemistry / Q000276:immunology
chemical_list: D000906:Antibodies; D000942:Antigens, Bacterial; D004187:Disaccharides; D006001:Glycoconjugates; D018796:Immunoconjugates