National Glycoengineering Research Center and Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University , 27 Shanda Nan Lu, Jinan 250100, China.
Qidong Dongyue Pharmaceutical Company, 268 Shanghai Road, Qidong, Jiangsu 226200, China.
Org Lett. 2017 Jun 16;19(12):3123-3126. doi: 10.1021/acs.orglett.7b01242. Epub 2017 May 26.
Two structurally defined, functionalized glycans of lipoteichoic acid (LTA, also known as PS-III) from C. difficile, which have one or two repeating units of LTA linked to the core trisaccharide, were efficiently synthesized via a convergent [2 + 3] or [2 + 2 + 3] strategy. The α-linkage of both N-acetylglucosamine residues in the repeating unit were constructed with glycosyl imidates of azidosugars as donors, while the phosphodiester bridges between the oligosaccharides were fashioned using H-phosphonate chemistry. Both synthetic targets contained a 3-aminopropyl group at the core trisaccharide reducing end, facilitating their conjugation to other biomolecules to afford conjugates useful for various biological studies and applications.
两种结构明确、功能化的艰难梭菌脂磷壁酸（LTA，也称为 PS-III）聚糖，它们的一个或两个 LTA 重复单元与核心三糖相连，通过收敛的 [2 + 3] 或 [2 + 2 + 3] 策略得到了高效合成。重复单元中两个 N-乙酰氨基葡萄糖残基的α-连接均采用叠氮糖的糖基亚氨基作为供体构建，而寡糖之间的磷酸二酯键则采用 H-膦酸酯化学方法构建。两个合成目标都在核心三糖还原端含有 3-氨基丙基，便于与其他生物分子缀合，得到用于各种生物学研究和应用的缀合物。
