English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT

Released

Journal Article

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

MPS-Authors

Tian,  Guangzong
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

/persons/resource/persons214142

Zou,  Xiaopeng
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

/persons/resource/persons248126

Cai,  Juntao
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

/persons/resource/persons121849

Seeberger,  Peter H.
Peter H. Seeberger - Vaccine Development, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

External Resource
No external resources are shared
Fulltext (public)
There are no public fulltexts stored in PuRe
Supplementary Material (public)
There is no public supplementary material available
Citation

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, 59(32), 13362-13370. doi:10.1002/anie.202004267.


Cite as: http://hdl.handle.net/21.11116/0000-0006-5FB2-7
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.