title: Synthesis of monodeoxy and mono-O-methyl congeners of methyl beta-D-mannopyranosyl-(1-->2)-beta-D-mannopyranoside for epitope mapping of anti-Candida albicans antibodies.
abstract: A panel of six complementary monodeoxy and mono-O-methyl congeners of methyl beta-d-mannopyranosyl-(1-->2)-beta-d-mannopyranoside (1) were synthesized by stereoselective glycosylation of monodeoxy and mono-O-methyl monosaccharide acceptors with a 2-O-acetyl-glucosyl trichloroacetimidate donor, followed by a two-step oxidation-reduction sequence at C-2'. The beta-manno configurations of the final deprotected congeners 2-7 were confirmed by measurement of (1)J(C1,H1) heteronuclear and (3)J(1',2') homonuclear coupling constants. These disaccharide derivatives will be used to map the protective epitope recognized by a protective anti-Candida albicans monoclonal antibody C3.1 (IgG3) and to determine its key polar contacts with the binding site.
authors.affiliation: Alberta Ingenuity Centre for Carbohydrate Science and Department of Chemistry, The University of Alberta, Gunning-Lemieux Chemistry Centre, Edmonton, AB, Canada T6G 2G2.
authors.forename: Corwin M
authors.initials: CM
authors.lastname: Nycholat
authors.forename: David R
authors.initials: DR
authors.lastname: Bundle
mesh_terms: D000908:Antibodies, Fungal / Q000737:chemistry* / Q000276:immunology*; D002176:Candida albicans / Q000276:immunology*; D002240:Carbohydrate Sequence; D018604:Epitope Mapping / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000138:chemical synthesis / Q000737:chemistry* / Q000276:immunology*; D015394:Molecular Structure
chemical_list: D000908:Antibodies, Fungal; D008358:Mannose