Laboratory of Organic Chemistry, Åbo Akademi University, FI-20500 Åbo, Finland.
Laboratory of Organic Chemistry, Åbo Akademi University, FI-20500 Åbo, Finland; Glykos Finland Ltd, Viikinkaari 6, 00790 Helsinki, Finland.
Carbohydr Res. 2014 Jan 13;383:58-68. doi: 10.1016/j.carres.2013.10.017. Epub 2013 Nov 9.
Phosphorylated β-(1→2)-oligomannosides are found on the cell surface of several Candida species, including Candida albicans (an opportunistic pathogen). These molecules are believed to take part in the invasion process of fungal infections, which in the case of C. albicans can lead to severe bloodstream infections and death, and can therefore be considered important from a biological standpoint. Understanding the mechanism of their action requires access to the corresponding oligosaccharide model compounds in pure form. In the present work, synthesis of the model core structures involved in the invasion process of C. albicans, consisting of phosphorylated β-(1→2)-linked mannotriose and tetraose, is reported. In order to elucidate the nature of these molecules in more detail, an extensive NMR-spectroscopic study encompassing complete spectral characterization, conformational analysis and molecular modelling was performed. The obtained results were also compared to similar chemical entities devoid of the charged phosphate group.
磷酸化的β-(1→2)-低聚糖存在于几种念珠菌属物种的细胞表面，包括白色念珠菌（一种机会性病原体）。这些分子被认为参与了真菌感染的入侵过程，在白色念珠菌的情况下，可能导致严重的血流感染和死亡，因此从生物学角度来看是很重要的。要了解它们作用的机制，需要获得相应的寡糖模型化合物的纯品形式。在本工作中，报道了参与白色念珠菌入侵过程的模型核心结构的合成，该结构由磷酸化的β-(1→2)-连接的甘露三糖和四糖组成。为了更详细地阐明这些分子的性质，进行了广泛的 NMR 光谱研究，包括完整的光谱表征、构象分析和分子建模。还将获得的结果与没有带电荷的磷酸基团的类似化学实体进行了比较。
