title: Chemo-bacterial synthesis and immunoreactivity of a brain HNK-1 analogue.
abstract: This work reports the synthesis and the biological validation of a trisaccharide analogue of the HNK-1 epitope. The 3-O-sulfo-β-d-GlcpA-(1→3)-β-d-Galp-(1→4)-β-d-Glcp-allyl has been prepared by enzymatic glucuronylation of allyl lactoside by an engineered recombinant Escherichia coli strain followed by a chemoselective sulfation. Subsequent covalent attachment of the ozone-oxidised trisaccharide to bovine serum albumin provided a neo-glycoconjugate, which has been interrogated with antibodies specific to the human natural killer carbohydrate epitope HNK-1. ELISA assays confirmed the absolute requirement of the sulfate group for protein recognition and the potential application of this synthetic oligosaccharide as HNK-1 surrogate.
authors.affiliation: Centre de Recherches sur les Macromolécules Végétales, 601 rue de la Chimie, BP 53X 38041 Grenoble, cedex 09, France.
authors.forename: Ludovic
authors.initials: L
authors.lastname: Bastide
authors.forename: Bernard
authors.initials: B
authors.lastname: Priem
authors.forename: Sébastien
authors.initials: S
authors.lastname: Fort
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry / Q000276:immunology / Q000378:metabolism*; D001921:Brain / Q000276:immunology; D018959:CD57 Antigens / Q000096:biosynthesis* / Q000737:chemistry / Q000276:immunology; D002240:Carbohydrate Sequence; D004797:Enzyme-Linked Immunosorbent Assay; D004926:Escherichia coli / Q000201:enzymology* / Q000235:genetics; D006801:Humans; D016056:Immunodominant Epitopes / Q000096:biosynthesis* / Q000737:chemistry / Q000276:immunology; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000096:biosynthesis* / Q000737:chemistry / Q000276:immunology; D012710:Serum Albumin, Bovine / Q000737:chemistry; D014312:Trisaccharides / Q000096:biosynthesis* / Q000737:chemistry / Q000276:immunology
chemical_list: D000498:Allyl Compounds; D018959:CD57 Antigens; D016056:Immunodominant Epitopes; D009844:Oligosaccharides; D014312:Trisaccharides; D012710:Serum Albumin, Bovine