Liao Guochao, Burgula Srinivas, Zhou Zhifang, Guo Zhongwu
Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI, 48202, USA.
European J Org Chem. 2015 May 1;2015(13):2942-2951. doi: 10.1002/ejoc.201500229.
β-Glucans are important carbohydrate antigens on the surface of fungal cells useful for antifungal vaccine development. This paper has described a highly convergent and efficient strategy for the synthesis of structurally defined branched β-glucan oligosaccharides that can be used for detailed studies of β-glucans and for the design of β-glucan-based vaccines. The strategy was highlighted by assembling the title compounds via preactivation-based glycosylation with thioglycosides as glycosyl donors. It was used to successfully prepare β-glucan oligosaccharides that had a β-1,3-linked nonaglucan backbone with β-1,6-glucotetraose, β-1,3-glucodiose and β-1,3-glucotetraose branches at the 6--position of the nonaglucan central sugar unit. The structure and size of the glycosyl donors and acceptors used in the syntheses did not significantly affect the glycosylation efficiency, suggesting that the strategy can be generally useful for the synthesis of more complex structures.
β-葡聚糖是真菌细胞表面重要的碳水化合物抗原，对开发抗真菌疫苗很有用。本文描述了一种高度收敛且高效的策略，用于合成结构明确的支链β-葡聚糖寡糖，可用于对β-葡聚糖的详细研究以及基于β-葡聚糖的疫苗设计。该策略的亮点是通过以硫代糖苷作为糖基供体的基于预活化的糖基化反应来组装目标化合物。利用该策略成功制备了β-葡聚糖寡糖，其具有β-1,3-连接的九糖骨架，在九糖中心糖单元的6位带有β-1,6-葡萄糖四糖、β-1,3-葡萄糖二糖和β-1,3-葡萄糖四糖分支。合成中使用的糖基供体和受体的结构和大小对糖基化效率没有显著影响，这表明该策略通常可用于合成更复杂的结构。
