Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Campylobacter jejuni [ICD11:
XN4Q5 
]
NCBI PubMed ID: 37266924Publication DOI: 10.1039/d3ob00683bJournal NLM ID: 101154995Publisher: The Royal Society of Chemistry
Correspondence: C.C. Ling <ccling
ucalgary.ca>
Institutions: Department of Chemistry, University of Calgary, 2500 University Drive NW, Calgary, Alberta T2N 1N4, Canada
Campylobacter jejuni is a bacterial pathogen that causes hundreds of millions of cases of food-borne gastroenteritis worldwide annually. The infection caused by this bacterium is also associated with several forms of post-infectious autoimmune sequelae that can be very serious, including the life-threatening Guillain-Barré syndrome. The capsular polysaccharides (CPS) of C. jejuni HS:4 consist of a very unique repeating disaccharide unit that is characterized by a β-1,4-linked 6-deoxy-β-D-ido-heptopyranose and an N-acetyl-β-D-glucosamine. Eliciting carbohydrate-specific antibodies against the CPS structures of C. jejuni HS:4 is an attractive strategy. The 6-deoxy-ido-configuration of the heptose combined with its β-anomeric configuration makes the chemical synthesis of the disaccharide very challenging. Here, we report an efficient synthesis to obtain the key repeating disaccharide and its analog in reverse order plus a trisaccharide. Our synthesis features a highly efficient, one-step stereo- and regioselective conversion of β-D-galacto-heptopyranosides to 6-deoxy-β-D-ido-heptopyranosides via the intermediate 2,3-anhydro-β-D-talo-heptopyranosides.
capsular polysaccharide, Campylobacter jejuni, chemical synthesis
Structure type: polymer chemical repeating unit
Location inside paper: p. 5047, Fig. 1
Compound class: CPS
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, glycosylation, optical rotation measurement, CC, HR-ESI-MS
NCBI Taxonomy refs (TaxIDs): 197
Show glycosyltransferases
There is only one chemically distinct structure:
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