The development of glycoconjugate vaccines against Helicobacter pylori is challenging. An exact epitope of the H. pylori lipo-polysaccharide (LPS) O-antigens that contain Lewis determinant oligosaccharides and unique dd-heptoglycans has not yet been identified. Reported here is the first total synthesis of H. pylori serotype O6 tridecasaccharide O-antigen containing a terminal Ley tetrasaccharide, a unique alpha-(1-3)-, alpha-(1-6)-, and alpha-(1-2)-linked heptoglycan, and a beta-d-galactose connector, by an [(2x1)+(3+8)] assembly sequence. Seven oligosaccharides covering different portions of the entire O-antigen were prepared for immunological investigations with a particular focus on elucidation of the roles of the dd-heptoglycan and Ley tetrasaccharide. Glycan microarray analysis of sera from rabbits immunized with isolated serotype O6 LPS revealed a humoral immune response to the alpha-(1-3)-linked heptoglycan, a key motif for designing glycoconjugate vaccines for H. pylori serotype O6.
NCBI PubMed ID: 32363752Publication DOI: 10.1002/anie.202004267Journal NLM ID: 0370543Publisher: Weinheim: Wiley-VCH
Correspondence: jianyin
jiangnan.edu.cn
Institutions: Key Laboratory of Carbohydrate Chemistry and Biotechnology, Ministry of Education, School of Biotechnology, Jiangnan University, Lihu Avenue 1800, Wuxi, Jiangsu Province, 214122, P. R. China, Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Muhlenberg 1, 14476, Potsdam, Germany, Wuxi School of Medicine, Jiangnan University, Lihu Avenue 1800, Wuxi, Jiangsu Province, 214122, P. R. China
Methods: 13C NMR, 1H NMR, chemical synthesis, chemical methods, glycosylation, immunological assays
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