Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Campylobacter jejuni [ICD11:
XN4Q5 
]
NCBI PubMed ID: 34260212Publication DOI: 10.1021/jacs.1c05048Journal NLM ID: 7503056Publisher: American Chemical Society
Correspondence: Ming Li <lmsnouc
ouc.edu.cn>
Institutions: Key Laboratory of Marine Medicine, Chinese Ministry of Education, Shandong Provincial Key Laboratory of Glycoscience and Glycotechnology, School of Medicine and Pharmacy, Ocean University of China, Qingdao, China, Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology, Qingdao, China
Campylobacter jejuni is the leading cause of human diarrheal diseases and has been designated as one of highly resistant pathogens by the World Health Organization. The C. jejuni capsular polysaccharides feature broad existence of uncommon 6dHepp residues and have proven to be potential antigens to develop innovative antibacterial glycoconjugation vaccines. To address the lack of synthetic methods for rare 6dHepp architectures of importance, we herein describe a novel and efficient approach for the preparation of uncommon d-/l-6dHepp fluorides that have power as glycosylating agents. The synthesis is achieved by a C1-to-C5 switch strategy relying on radical decarboxylative fluorination of uronic acids arising from readily available allyl d-C-glycosides. To further showcase the application of this protocol, a structurally unique hexasaccharide composed of →3)-β-d-6didoHepp-(1→4)-β-d-GlcpNAc-(1→ units, corresponding to the capsular polysaccharide of C. jejuni strain CG8486 has been assembled for the first time. The assembly is characterized by highly efficient construction of the synthetically challenging β-(1,2-cis)-d-ido-heptopyranoside by inversion of the C2 configuration of β-(1,2-trans)-d-gulo-heptopyranoside, which is conveniently obtained by anchimerically assisted stereoselective glycosylation of the orthogonally protected 6dgulHepp fluoride. Ready accessibility of 6dHepp fluorides and the resulting glycans could serve as a rational starting point for the further development of synthetic vaccines fighting Campylobacter infection.
synthesis, capsular polysaccharides, Campylobacter jejuni, d-/l-6dHepp fluorides
Structure type: polymer chemical repeating unit
Location inside paper: p. 11172, Fig 1, structure 5, C. jejuni HS53
Compound class: CPS
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, UV, RP-HPLC, HR-ESI-MS
Related record ID(s): 9678, 9679, 9680, 9681, 10895
NCBI Taxonomy refs (TaxIDs): 197Reference(s) to other database(s): GTC:G57727ID, GlycomeDB:
34688
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There is only one chemically distinct structure:
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