Chemical synthesis and biological evaluation of penta- to octa- saccharide fragments of Vi polysaccharide fromSalmonella typhi

Autor: Meng-Man Wei, Xin-Shan Ye, Gao-Lan Zhang, De-Cai Xiong, Yu-Feng Ma, Chengcheng Song, Xiu-Jing Zheng
Rok vydání: 2018
Předmět:
Zdroj: Organic Chemistry Frontiers. 5:2179-2188
ISSN: 2052-4129
DOI: 10.1039/c8qo00471d
Popis: Vi antigen is the capsular polysaccharide of Salmonella typhi, which can cause typhoid fever. With the increasing threat of antiboitic resistance, vaccination against Salmonella typhi is a preferred way to prevent this disease. Chemical synthesis of fragments of Vi antigen is in urgent need for the development of structure-homogeneous and quality-controlled oligosaccharide vaccines. However, it is extremely challenging to synthesize large oligosaccharide fragments of Vi antigen owing to the exclusive α-1,4-linkage of polyaminogalacturonates. Herein, a series of Vi oligosaccharides ranging from pentamer to octamer were efficiently prepared using 2,3-N,O-oxazolidinone protected glycosides as building blocks based on the preactivation protocol. The heptasaccharide and octasaccharide fragments were synthesized for the first time. The competitive ELISA evaluation suggested that the hexasaccharide might be the minimum epitope of Vi antigen, which provides a significant guidance for the future development of Vi oligosaccharide vaccines.
Databáze: OpenAIRE