Nycholat Corwin M, Bundle David R
Alberta Ingenuity Centre for Carbohydrate Science and Department of Chemistry, The University of Alberta, Gunning-Lemieux Chemistry Centre, Edmonton, AB, Canada T6G 2G2.
Carbohydr Res. 2009 Mar 31;344(5):555-69. doi: 10.1016/j.carres.2008.12.011. Epub 2008 Dec 24.
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.
通过用2-O-乙酰基-葡萄糖基三氯乙酰亚胺供体对单脱氧和单-O-甲基单糖受体进行立体选择性糖基化反应，然后在C-2'处进行两步氧化还原序列反应，合成了一组六个甲基β-D-甘露吡喃糖基-(1→2)-β-D-甘露吡喃糖苷(1)的互补单脱氧和单-O-甲基同系物。通过测量(1)J(C1,H1)异核和(3)J(1',2')同核耦合常数，确认了最终脱保护同系物2-7的β-甘露糖构型。这些二糖衍生物将用于绘制保护性抗白色念珠菌单克隆抗体C3.1(IgG3)识别的表位图谱，并确定其与结合位点的关键极性接触。
