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.
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 configuration of the final deprotected congeners 2-7 was 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 epitope recognized by a protective anti-Candida albicans monoclonal antibody C3.1 (IgG3) and to determine its key polar contacts with the binding site.
Nycholat
Corwin M
CM
Alberta Ingenuity Centre for Carbohydrate Science and Department of Chemistry, The University of Alberta, Gunning-Lemieux Chemistry Centre, Edmonton, AB, Canada T6G 2G2.
Bundle
David R
DR
D000818:Animals; D000911:Antibodies, Monoclonal / Q000276:immunology*; D000946:Antigens, Fungal / Q000737:chemistry* / Q000276:immunology*; D002176:Candida albicans / Q000276:immunology*; D002240:Carbohydrate Sequence; D018604:Epitope Mapping / Q000379:methods*; D008358:Mannose / Q000138:chemical synthesis* / Q000737:chemistry* / Q000276:immunology; D008969:Molecular Sequence Data; D015394:Molecular Structure
D000911:Antibodies, Monoclonal; D000946:Antigens, Fungal; D008358:Mannose