Synthesis of monodeoxy and mono-O-methyl congeners of methyl β-d-mannopyranosyl-(1→2)-β-d-mannopyranoside for epitope mapping of anti-Candida albicans antibodies |
| |
Authors: | Corwin M. Nycholat David R. Bundle |
| |
Affiliation: | aAlberta Ingenuity Centre for Carbohydrate Science and Department of Chemistry, The University of Alberta, Gunning-Lemieux Chemistry Centre, Edmonton, AB, Canada T6G 2G2 |
| |
Abstract: | A panel of six complementary monodeoxy and mono-O-methyl congeners of methyl β-d-mannopyranosyl-(1→2)-β-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 β-manno configurations of the final deprotected congeners 2–7 were confirmed by measurement of 1JC1,H1 heteronuclear and 3J1′,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. |
| |
Keywords: | Methyl β - smCaps" >d-mannopyranosyl-(1→ 2)-β - smCaps" >d-mannopyranoside Monodeoxy and mono-O-methyl congeners Mapping of anti-Candida albicans antibodies Functional group modification |
本文献已被 ScienceDirect 等数据库收录! |