Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Campylobacter jejuni [ICD11:
XN4Q5 
]
The structure was elucidated in this paperNCBI PubMed ID: 37040604Publication DOI: 10.1021/jacs.3c00102Journal NLM ID: 7503056Publisher: American Chemical Society
Correspondence: C.C. Wang <wangcc7280
gate.sinica.edu.tw>
Institutions: Institute of Chemistry, Academia Sinica, 128 Section 2, Academia Road, Taipei 115, Taiwan, Chemical Biology and Molecular Biophysics (CBMB), Taiwan International Graduate Program (TIGP), Academia Sinica, 128 Section 2, Academia Road, Taipei 115, Taiwan
The infection of Campylobacter jejuni results in a significant diarrhea disease, which is highly fatal to young children in unindustrialized countries. Developing a new therapy is required due to increasing antibiotic resistance. Herein, we described a total synthesis of a C. jejuni NCTC11168 capsular polysaccharide repeating unit containing a linker moiety via an intramolecular anomeric protection (iMAP) strategy. This one-step 1,6-protecting method structured the challenging furanosyl galactosamine configuration, facilitated further concise regioselective protection, and smoothed the heptose synthesis. The tetrasaccharide was constructed in a [2 + 1 + 1] manner. The synthesis of this complicated CPS tetrasaccharide was completed in merely 28 steps, including the preparation of all the building blocks, construction of the tetrasaccharide skeleton, and functional group transformations.
capsular polysaccharide, Campylobacter jejuni, total synthesis
Structure type: oligomer ; 987.3901 [M+H]+
C
36H
68N
4O
25P
Location inside paper: scheme 1, p. 9007, scheme 7, compound 1
Aglycon: 5-aminopentyl
Compound class: CPS
Contained glycoepitopes: IEDB_115136,IEDB_137473,IEDB_140630,IEDB_149136
Methods: 13C NMR, 1H NMR, IR, TLC, 31P NMR, chemical synthesis, UV, glycosylation, optical rotation measurement, HR-ESI-MS, DEPT, flash chromatography
Synthetic data: chemical
Related record ID(s): 22343
NCBI Taxonomy refs (TaxIDs): 197
Show glycosyltransferases
There is only one chemically distinct structure:
Found 
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