铜绿假单胞菌O19血清型表面脂多糖二糖抗原的化学合成
首发时间:2023-10-31
摘要:铜绿假单胞菌是一种引起肺炎、菌血症的超级耐药菌。铜绿假单胞菌表面脂多糖(LPS)是糖疫苗开发的重要靶标分子。铜绿假单胞菌O19血清型O抗原二糖片段结构为α-L-GalNAcA-(1,3)-α-D-QuiNAc。利用苄叉基的环构像锁定效应,高立体选择性实现了L-半乳糖-1,2-顺式糖苷键的构建。与硒苯基离去基团相比,使用活性更高的三氟乙酰亚胺酯基供体可大幅提高二糖偶联顺序。合成制备的二糖片段端基位含氨基连接臂,可为后续对二糖的抗原性及免疫活性分析作准备,进一步探究其作为糖疫苗的可行性。
关键词: 铜绿假单胞菌 脂多糖抗原 化学合成 1,2-顺式-糖苷键
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Chemical Synthesis of Lipopolysaccharide of Pseudomonas Aeruginosa Serotype O19 Disaccharide O-antigen
Abstract:Pseudomonas aeruginosa is a super-resistant bacterium that causes pneumonia and bacteremia. Lipopolysaccharides (LPS) of Pseudomonas aeruginosa are potential target molecules for carbohydrate-based vaccine development. The structure of Pseudomonas aeruginosa O19 serotype O-antigen disaccharide is α-L-GalNAcA-(1,3)-α-D-QuiNAc。The 1,2-cis glycosidic bond of L-galactoside was achieved by conformational locking of benzylidene group. The glycosylation efficiency has been improved by coupled acceptor with more reactive trifluoroacetamide donor instead of selenophenyl donor. To explore its feasibility as a carbohydrate-based vaccine in the future, the reducing end of the disaccharide was installed with an amino linker for antigenicity analyzing and immunity studying and to explore its feasibility as a carbohydrate-based vaccine in the future.
Keywords: Pseudomonas aeruginosa Lipopolysaccharide O-antigen Chemical synthesis 1,2-cis glycosidic bond
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铜绿假单胞菌O19血清型表面脂多糖二糖抗原的化学合成
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