Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: diarrhea [ICD11:
ME05.1 
, ICD11:
SA55 ];
infection due to Campylobacter jejuni [ICD11:
XN4Q5 ]
NCBI PubMed ID: 26513759Publication DOI: 10.1016/j.carres.2015.09.012Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: monteiro
uoguelph.ca
Institutions: Department of Chemistry, University of Guelph, Guelph, ON, Canada N1G 2W1, Enteric Diseases Department, Naval Medical Research Centre, Silver Spring, MD, USA
Campylobacter jejuni is a leading cause of traveler's diarrhea. Previously, we have shown that a C. jejuni capsule polysaccharide (CPS) conjugate vaccine can fully prevent C.jejuni diarrhea in non-human primates. C.jejuni CPSs are decorated with non-stoichiometric amounts of O-methyl phosphoramidate (MeOPN) units that are key serospecific markers. In the case of C.jejuni serotype complex HS23/36, the MeOPN are at positions 2 and 6 of the CPS galactose (Gal). We describe here the synthesis of the p-methoxyphenyl glycoside of MeOPN→6-α-D-Galp, and its immunodetection by antisera raised by C.jejuni CPS conjugates with MeOPN at primary positions. The synthetic approach in this work served as the foundation for a similar MeOPN→6-Gal construct used in a conjugate vaccine, whose synthesis, immunogenicity and efficacy will be described elsewhere.
synthesis, Campylobacter jejuni, capsule polysaccharide, conjugate vaccine, O-methyl phosphoramidate, Traveler's diarrhea vaccine
Structure type: fragment of a bigger structure
Location inside paper: p.9
Compound class: CPS
Contained glycoepitopes: IEDB_135813,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,SB_173,SB_7
Methods: 13C NMR, 1H NMR, TLC, 31P NMR, ESI-MS, chemical synthesis, chemical methods, immunoblotting
NCBI Taxonomy refs (TaxIDs): 197
Show glycosyltransferases
There is only one chemically distinct structure:
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