Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: campylobacteriosis [ICD11:
1C40 
, ICD11:
XN4Q5 ];
infection due to Campylobacter jejuni [ICD11:
XN4Q5 ]
NCBI PubMed ID: 28809484Publication DOI: 10.1021/acs.joc.7b01752Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: Chang-Chun Ling <ccling
ucalgary.ca>
Institutions: Alberta Glycomics Centre, Department of Chemistry, University of Calgary, Calgary, AB, Canada
The 6-deoxy-β-D-ido-heptopyranoside related to the capsular polysaccharides of C. jejuni HS:4 is very remarkable, owing to the unique, multifaceted structural features that have been combined into one molecule, which include (1) the rare ido-configuration, (2) the unusual 7-carbon backbone, and (3) the challenging β-(1→2)-cis-anomeric configuration. Two distinct strategies toward the total synthesis of this interesting target are reported. The first involved establishment of the β-D-idopyranosyl configuration from β-D-galactopyranosides, prior to a C-6-homologation extending the D-hexose to the desired 6-deoxy-D-heptose. However, this approach encountered difficulties due to the significantly reduced reactivity of the 6-position of the β-D-idopyranosides, so instead a second strategy was employed, which involved first carrying out a 6-homologation on the less flexible D-galactopyranose, followed by a very successful conversion to the desired β-D-ido-configuration found in the target heptopyranoside (2). This report is the first successful synthesis of the 6-deoxy-β-D-ido-heptopyranoside, which could possess interesting immunological properties.
capsular polysaccharide, total synthesis, 6-deoxy-β-D-ido-heptopyranoside, Campylobacter jejuni HS:4
Structure type: polymer chemical repeating unit
Location inside paper: p.9663, fig.1
Compound class: CPS
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_151531
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, glycosylation, ion-exchange chromatography, optical rotation measurement, ESI-QTOF-MS
NCBI Taxonomy refs (TaxIDs): 197
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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