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

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Abstract

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.

Graphical abstract: Chemical synthesis and biological evaluation of penta- to octa- saccharide fragments of Vi polysaccharide from Salmonella typhi

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Publication details

The article was received on 14 May 2018, accepted on 04 Jun 2018 and first published on 07 Jun 2018


Article type: Research Article
DOI: 10.1039/C8QO00471D
Citation: Org. Chem. Front., 2018, Advance Article
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    Chemical synthesis and biological evaluation of penta- to octa- saccharide fragments of Vi polysaccharide from Salmonella typhi

    G. Zhang, M. Wei, C. Song, Y. Ma, X. Zheng, D. Xiong and X. Ye, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00471D

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