Hofinger A, Kosma P, Christian R, Bock K, Brade H
Institut für Chemie, Universität für Bodenkultur, Vienna, Austria.
Carbohydr Res. 1993 May 7;243(2):273-91. doi: 10.1016/0008-6215(93)87033-o.
The disaccharides O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2-->8)-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (8), O-L-glycero-alpha-D-manno-heptopyranosyl-(1-->7)-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (12), and O-alpha-D-mannopyranosyl-(1-->7)-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (21) and the branched trisaccharides O-L-glycero-alpha-D-manno-heptopyranosyl-(1-->7)-[O-(sodium 3-deoxy-alpha- and -beta-D-manno-2-octulopyranosylonate)-(2-->8)]-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (15 and 16) and O-alpha-D-mannopyranosyl-(1-->7)-[O-(sodium 3-deoxy-alpha-D-manno-2-octulopyranosylonate)-(2-->8)]-sodium (allyl 3-deoxy-beta-D-manno-2-octulopyranosid)onate (24) were prepared. Per-O-acetylated mannopyranosyl or Kdo bromide derivatives were employed for the glycosylation steps under Helferich conditions, whereas the imidate derivative 9 was used for the coupling of the L-glycero-D-manno-heptopyranosyl residues. The oligosaccharides were fully characterized by NMR spectroscopic data. Their structures correspond to an artificial linkage pattern providing a potential cross-reactive epitope for antibodies directed against the inner-core-region of enterobacterial as well as chlamydial lipopolysaccharides.
制备了二糖O-(3-脱氧-α-D-甘露-2-辛吡喃糖醛酸根钠)-(2→8)-（烯丙基3-脱氧-β-D-甘露-2-辛吡喃糖苷）酸根钠(8)、O-L-甘油-α-D-甘露庚吡喃糖基-(1→7)-（烯丙基3-脱氧-β-D-甘露-2-辛吡喃糖苷）酸根钠(12)和O-α-D-甘露吡喃糖基-(1→7)-（烯丙基3-脱氧-β-D-甘露-2-辛吡喃糖苷）酸根钠(21)，以及支链三糖O-L-甘油-α-D-甘露庚吡喃糖基-(1→7)-[O-(3-脱氧-α-和-β-D-甘露-2-辛吡喃糖醛酸根钠)-(2→8)]-（烯丙基3-脱氧-β-D-甘露-2-辛吡喃糖苷）酸根钠(15和16)和O-α-D-甘露吡喃糖基-(1→7)-[O-(3-脱氧-α-D-甘露-2-辛吡喃糖醛酸根钠)-(2→8)]-（烯丙基3-脱氧-β-D-甘露-2-辛吡喃糖苷）酸根钠(24)。在Helferich条件下，使用全-O-乙酰化甘露吡喃糖基或Kdo溴化物衍生物进行糖基化步骤，而亚氨酸酯衍生物9用于连接L-甘油-D-甘露庚吡喃糖基残基。通过核磁共振光谱数据对寡糖进行了全面表征。它们的结构对应于一种人工连接模式，为针对肠杆菌和衣原体脂多糖内核区域的抗体提供了潜在的交叉反应表位。
