Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
];
infection due to Salmonella enterica [ICD11:
XN5VC ]
NCBI PubMed ID: 24359545Publication DOI: 10.1021/jo402312xJournal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: paul.kosma
boku.ac.at
Institutions: Department of Chemistry, University of Natural Resources and Life Sciences , A-1190 Vienna, Austria
The structurally conserved lipopolysaccharide core region of many Gram-negative bacteria is composed of trisaccharides containing 4-O-phosphorylated L-glycero-D-manno-heptose (L,D-Hep) units, which act as ligands for antibodies and lectins. The disaccharides Glc-(1→3)-Hep4P Hep-(1→3)-Hep4P and Hep-(1→7)-Hep4P and the branched trisaccharide Glc-(1→3)-[Hep-(1→7)]-Hep4P, respectively, have been synthesized from a methyl heptopyranoside acceptor in less than 10 steps. The synthetic strategy was based on the early introduction of a phosphotriester at position 4 of heptose followed by a regioselective opening of a 6,7-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl) group allowing for a straightforward access to glycosylation at position 7. Perbenzylated N-phenyl trifluoroacetimidate glucosyl and heptosyl derivatives served as alpha-selective glycosyl donors.
Lipopolysaccharide, synthesis, core oligosaccharide, gram negative bacteria, glycosylation
Structure type: oligomer ; 657.1643 [M-H]-
C
21H
38O
21P
Location inside paper: p. 586, scheme 6, compound 42
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130670,IEDB_133751,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_2189047,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, 31P NMR, chemical synthesis, chemical methods, HPLC, UV, glycosylation, ESI-TOF-MS, HPLC-MS
Synthetic data: chemical
Comments, role: synthetic trisaccharide
Related record ID(s): 30136, 30467, 30468, 30469, 30470
NCBI Taxonomy refs (TaxIDs): 562,
28901
Show glycosyltransferases
1H NMR data: present in publication
|
13C NMR data: present in publication
|
There is only one chemically distinct structure:
Found 
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