Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China, University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
Org Biomol Chem. 2019 Feb 13;17(7):1694-1697. doi: 10.1039/c8ob02340a.
The first construction of the challenging β-(1 → 5)-linked GalNAc-Kdo skeleton is described for the synthesis of the disaccharide antigen of the capsular polysaccharide of Kingella kingae KK01. TfOH-catalyzed glycosylation of N-Troc-protected d-galactosaminyl N-phenyl trifluoroacetimidate with a sterically hindered 5-hydroxyl group of the β-Kdo building block in toluene proceeded smoothly to provide the desired disaccharide in excellent yield with satisfactory β-selectivity. An optimal sequence for the deprotection of the disaccharide skeleton was found to access the disaccharide antigen of Kingella kingae KK01 for further immunological studies.
首次构建了具有挑战性的β-（1 → 5）-连接的 GalNAc-Kdo 骨架，用于合成金氏金菌 KK01 荚膜多糖的二糖抗原。在三氟乙酸催化下，N-Troc 保护的 d-半乳糖胺基 N-苯三氟乙酰亚胺与β-Kdo 砌块的位阻 5-羟基在甲苯中进行糖苷化反应，以优异的产率和良好的β选择性得到所需的二糖。发现了一种最佳的脱保护顺序，可以获得金氏金菌 KK01 的二糖抗原，用于进一步的免疫学研究。
