Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: chronic gastritis [ICD11:
DA42.Z 
, ICD11:
XT8W ];
peptic ulcer [ICD11:
DA61 , ICD11:
XN3DY ];
infection due to Helicobacter pylori [ICD11:
XN3DY ]
The structure was elucidated in this paperNCBI PubMed ID: 22486825Publication DOI: 10.1016/j.carres.2012.03.013Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: yukarif
chem.sci.osaka-u.ac.jp (Y. Fujimoto)
Institutions: Department of Chemistry, Graduate School of Science, Osaka University, 1-1 Machikaneyama Toyonaka, Osaka 560-0043, Japan
Helicobacter pylori, a Gram-negative bacterium, causes gastroduodenal inflammatory diseases such as chronic gastritis and peptic ulcers, and is also a risk factor for gastric carcinogenesis. In this article, we review recent developments and findings in the chemical synthesis and immunomodulatory activities of H. pylori lipid A and 3-deoxy-d-manno-2-octulosonic acid (Kdo)-lipid A, to clarify the structural basis for the inflammatory response to H. pylori LPS. The synthetic methods include a new divergent synthetic approach with a widely applicable key intermediate for other types of lipid A structures, as well as a selective α-glycosylation reaction between Kdo and lipid A. Cytokine induction assays of the chemically synthesized lipid A structures showed selective cytokine induction depending on the patterns of acyl groups and phosphate groups. The results of cytokine induction assay suggested that H. pylori LPS can modulate the immune response during infection, and also plays a role in chronic inflammatory responses.
Lipopolysaccharide, lipid A, Helicobacter pylori, glycosylation, microfluidic reaction
Structure type: oligomer
Location inside paper: p.39, fig.2, p.41, scheme 3, 10b (HpKdoLA)
Contained glycoepitopes: IEDB_130650,IEDB_141807,IEDB_151531,IEDB_534865
Methods: ELISA, chemical methods, glycosylation
Biological activity: assays of the immunomodulatory activites of the synthetic lipid A and Kdo-lipid A
Synthetic data: chemical
Related record ID(s): 27156
NCBI Taxonomy refs (TaxIDs): 210
Show glycosyltransferases
There is only one chemically distinct structure:
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