Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Campylobacter jejuni [ICD11:
XN4Q5 
]
The structure was elucidated in this paperNCBI PubMed ID: 30280458Publication DOI: 10.1002/anie.201810222Journal NLM ID: 0370543Publisher: Weinheim: Wiley-VCH
Correspondence: tlowary
ualberta.ca
Institutions: Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada
The O-methyl phosphoramidate (MeOPN) motif is a non-stoichiometric modification of capsular polysaccharides (CPS) in ?70?% of all Campylobacter jejuni strains. Infections by C. jejuni lead to food-borne illnesses and the CPS they produce are key virulence factors. The MeOPN phosphorus atom in these CPS is stereogenic and is found as a single stereoisomer. However, to date, the absolute stereochemistry at this atom has been undefined. We report the synthesis of the three repeating units found in C. jejuni 81-176 CPS; one of these possesses a MeOPN group. In the course of these studies we established that the stereochemistry of the phosphorus atom in this MeOPN group is R. These studies represent the first unequivocal proof of stereochemistry of this group in any C. jejuni CPS. The compounds produced are anticipated to be useful tools in investigations targeting the function and biosynthesis of this structurally-interesting modification, which so far has only been identified in campylobacter.
capsular polysaccharide, Campylobacter jejuni, NMR spectroscopy, glycosylation, phosphoramidate, 6-deoxyheptose
Structure type: oligomer ; 794.3682 [M+H]+
C
31H
61N
3O
18P
Location inside paper: fig.1, S29-S30, compound 3
Aglycon: (->1) 8-aminooctyl
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, NMR-2D, TLC, 31P NMR, ESI-MS, chemical synthesis, chemical methods, glycosylation, optical rotation measurement
Synthetic data: chemical
Comments, role: repeating unit
Related record ID(s): 12804, 12988
NCBI Taxonomy refs (TaxIDs): 354242
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There is only one chemically distinct structure:
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