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  Chemical synthesis and immunological evaluation of Helicobacter pylori serotype O6 tridecasaccharide O-antigen containing a unique DD-heptoglycan

Tian, G., Hu, J., Qin, C., Li, L., Zou, X., Cai, J., et al. (2020). Chemical synthesis and immunological evaluation of Helicobacter pylori serotype O6 tridecasaccharide O-antigen containing a unique DD-heptoglycan. Angewandte Chemie International Edition. doi:10.1002/anie.202004267.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0006-5FB2-7 Version Permalink: http://hdl.handle.net/21.11116/0000-0006-8B34-3
Genre: Journal Article

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 Creators:
Tian, Guangzong1, Author
Hu, Jing, Author
Qin, Chunjun, Author
Li, Lingxin, Author
Zou, Xiaopeng1, Author              
Cai, Juntao1, Author              
Seeberger, Peter H.1, Author              
Yin, Jian, Author
Affiliations:
1Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863308              

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Free keywords: Helicobacter pylori, Immunology, O-antigen, Total synthesis, tridecasaccharide
 Abstract: The development of glycoconjugate vaccines against Helicobacter pylori is challenging. An exact epitope of the H. pylori lipopolysaccharides (LPS) O-antigens that contain Lewis determinant oligosaccharides and unique DD-heptoglycans has not yet been identified. Here, we report the first total synthesis of H. pylori serotype O6 tridecasaccharide O-antigen containing a terminal Ley tetrasaccharide, a unique α-(1→3)-, α-(1→6)- and α-(1→2)-linked heptoglycan, and a ?-D-galactose connector through an [(2 x 1) + (3 + 8)] assembly sequence, which may serve as reference for the syntheses of other sterically hindered long-chain glycans. 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 DD-heptoglycan and Ley tetrasaccharide. Glycan microarrays analysis of sera from rabbits immunized with isolated serotype O6 LPS revealed a humoral immune response to the α-(1→3)-linked heptoglycan, which is the key motif for designing glycoconjugate vaccines for H. pylori serotype O6.

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Language(s): eng - English
 Dates: 2020-05-03
 Publication Status: Published online
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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: - Sequence Number: - Start / End Page: - Identifier: ISSN: 1433-7851

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Title: Angewandte Chemie
  Abbreviation : Angew. Chem.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: - Sequence Number: - Start / End Page: - Identifier: ISSN: 0044-8249