Abronina Polina I, Malysheva Nelly N, Karpenko Maxim Y, Novikov Dmitry S, Zinin Alexander I, Kolotyrkina N G, Kononov Leonid O
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp., 47, Moscow 119991, Russia.
Molecules. 2025 Aug 6;30(15):3295. doi: 10.3390/molecules30153295.
A rational synthesis of the branched decaarabinofuranoside with 4-(2-azidoethoxy)phenyl aglycone (a Janus aglycone) related to the non-reducing terminal fragments of the arabinogalactan and lipoarabinomannan from was proposed. Since the most challenging step is the formation of a 1,2- glycosidic linkage, we have significantly simplified access to a library of oligoarabinofuranosides derived from polysaccharides using a silylated Ara-β-(1→2)-Ara disaccharide as the glycosyl donor. The application of a Janus aglycone also allowed us to reduce the number of reaction steps in glycoside synthesis. The obtained arabinans can be useful to further prepare conjugates as antigens for creating tuberculosis screening assays.
提出了一种与来自阿拉伯半乳聚糖和脂阿拉伯甘露聚糖的非还原末端片段相关的、具有4-(2-叠氮基乙氧基)苯基苷元（一种双功能苷元）的支链十碳阿拉伯呋喃糖苷的合理合成方法。由于最具挑战性的步骤是形成1,2-糖苷键，我们使用硅烷化的Ara-β-(1→2)-Ara二糖作为糖基供体，显著简化了从多糖衍生的低聚阿拉伯呋喃糖苷库的获取。双功能苷元的应用还使我们能够减少糖苷合成中的反应步骤。所获得的阿拉伯聚糖可用于进一步制备作为抗原的缀合物，以创建结核病筛查测定法。
