Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: chronic gastritis [ICD11:
DA42.Z 
, ICD11:
XT8W ];
peptic ulcer [ICD11:
DA61 , ICD11:
XN3DY ];
gastric cancer [ICD11:
2B72.Z ];
infection due to Helicobacter pylori [ICD11:
XN3DY ]
The structure was elucidated in this paperNCBI PubMed ID: 29319212Publication DOI: 10.1002/chem.201800049Journal NLM ID: 9513783Publisher: Weinheim: VCH Verlagsgesellschaft/Verlag I
Correspondence: peter.seeberger
mpikg.mpg.de; 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 Mhlenberg 1, 14476 Potsdam (Germany)
Helicobacter pylori, a widespread gastric bacterial pathogen that infects 90% of the population in developing countries, causes chronic gastritis, peptic ulcers and gastric cancer. Battling H. pylori infection is a serious challenge due to the increased resistance to antibiotics and the lack of vaccines. The lipopolysaccharide covering the H. pylori cell-surface outer membrane is an attractive target for the development of a glycoconjugate vaccine. Here, we report a [3+5] convergent synthesis of an outer core octasaccharide of H. pylori employing just three orthogonally protected building blocks. A synergistic glycosylation strategy enables the creation of five pivotal 1,2-cis-α-glucosidic bonds consist of four types of linkages using just three monomers. This strategy can be expanded to many 1,2-cis-α-glucoside-containing oligosaccharides both in solution and on solid phase.
Oligosaccharides, bacteria, glycosylation, 1, carbohydrate chemistry, 2-cis-α-glucosides, synergistic glycosylation
Structure type: oligomer
Location inside paper: p.2, scheme 1, compound 2
Aglycon: (->1) 5-aminopentyl
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_136044,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158538,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_2346541,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, TLC, ESI-MS, chemical synthesis, MALDI-TOF MS, glycosylation
Synthetic data: chemical
Related record ID(s): 13016
NCBI Taxonomy refs (TaxIDs): 210Reference(s) to other database(s): GTC:G82043TI
Show glycosyltransferases
There is only one chemically distinct structure:
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