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  Chemical synthesis of the highly sterically hindered core undecasaccharide of Helicobacter pylori lipopolysaccharide for antigenicity evaluation with human serum

Zou, X., Hu, J., Zhao, M., Qin, C., Zhu, Y., Tian, G., et al. (2022). Chemical synthesis of the highly sterically hindered core undecasaccharide of Helicobacter pylori lipopolysaccharide for antigenicity evaluation with human serum. Journal of the American Chemical Society, 144(32), 14535-14547. doi:10.1021/jacs.2c03068.

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Zou, Xiaopeng1, Author           
Hu, Jing, Author
Zhao, Ming, Author
Qin, Chunjun, Author
Zhu, Yuntao2, Author           
Tian, Guangzong, Author
Cai, Juntao, 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              
2Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863306              

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 Abstract: Helicobacter pylori, listed as a human carcinogen by the Department of Health and Human Services, colonizes the gastric mucosa of more than half of the world’s population. The individuals infected with H. pylori have a high risk to develop chronic gastritis, peptic ulcers, and even gastric cancer. The conserved core structure of H. pylori lipopolysaccharide (LPS) has been regarded as a promising candidate structure for development of a glycoconjugate vaccine targeting multiple serotypes. Here, we report a total synthesis of the core undecasaccharide of H. pylori LPS and its subunit antigens. The match and mismatch between the glycosyl donor and acceptor caused by the inert hydroxyl groups were addressed by a judicious choice of orthogonal protection strategies and glycosylation conditions. A combination of acyl remote participation and solvent effects has been applied for selective formation of the five 1,2-cis-glucosidic bonds. The high steric hindrance induced by the high carbon sugars and trinacriform architecture required that the core undecasaccharide was synthesized through a finely tuned linear assembly [2 + (1 + (3 + (1 + (1 + 3))))] rather than convergent strategies. An antigenicity evaluation using glycan microarrays showed that an α-(1 → 6)-glucan trisaccharide is recognized by IgG antibodies in sera of H. pylori-infected patients. The phosphate group of the inner core trisaccharide key epitope is very important for IgG recognition. These findings are an important step toward designing carbohydrate-based vaccines against H. pylori.

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Language(s): eng - English
 Dates: 2022-08-082022
 Publication Status: Published in print
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 Identifiers: DOI: 10.1021/jacs.2c03068
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Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 144 (32) Sequence Number: - Start / End Page: 14535 - 14547 Identifier: ISSN: 0002-7863