Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Burkholderia [ICD11:
XN01M 
];
infection due to Proteus [ICD11:
XN3BS ]
The structure was elucidated in this paperNCBI PubMed ID: 23136534Publication DOI: 10.1002/ejoc.201101171Journal NLM ID: 9805750Publisher: Wiley-VCH
Correspondence: paul.kosma
boku.ac.at
Institutions: Department of Chemistry, University of Natural Resources and Life Sciences Muthgasse 18, 1190 Vienna, Austria
Disaccharides that contain 3-deoxy-d-manno-oct-2-ulosonic acid (Kdo) and d-glycero-d-talo-oct-2-ulosonic acid (Ko) substituted at the 8-position by 4-amino-4-deoxy-β-L-arabinopyranosyl (Ara4N) residues have been prepared. Coupling an N-phenyltrifluoroacetimidate-4-azido-4-deoxy-l-arabinosylglycosyl donor to acetyl-protected allyl glycosides of Kdo and Ko afforded anomeric mixtures of disaccharide products in 74 and 90 % yield, respectively, which were separated by chromatography. Further extension of an intermediate Ara4N-(1→8)-Kdo disaccharide acceptor, which capitalized on a regioselective glycosylation with a Kdo bromide donor under Helferich conditions, afforded the branched trisaccharide α-Kdo-(2→4)[β-L-Ara4N-(1→8)]-α-Kdo derivative. Deprotection of the protected di- and trisaccharide allyl glycosides was accomplished by TiCl(4)-promoted benzyl ether cleavage followed by the removal of ester groups and reduction of the azido group with thiol or Staudinger reagents, respectively. The reaction of the anomeric allyl group with 1,3-propanedithiol under radical conditions afforded the thioether-bridged spacer glycosides, which were efficiently coupled to maleimide-activated bovine serum albumin. The neoglycoconjugates serve as immunoreagents with specificity for inner core epitopes of Burkholderia and Proteus lipopolysaccharides.
Lipopolysaccharide, carbohydrates, Burkholderia, glycoconjugates, Proteus, glycosylation, glycolipids, Biomimetic synthesis
Structure type: oligomer
Location inside paper: p.122, scheme 5, 41, scheme 6, 43
Aglycon: Allyl or BSA
Trivial name: part of the LPS
Compound class: neoglycoconjugate
Contained glycoepitopes: IEDB_130650,IEDB_130659
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, MALDI-TOF MS, glycosylation, conjugation, HPLC-HRMS
Synthetic data: chemical
Comments, role: Origin: Burkholderia sp. and Proteus sp. without species and strain assignment.
Related record ID(s): 27121, 28311
NCBI Taxonomy refs (TaxIDs): 32008,
583Reference(s) to other database(s): GTC:G51773XB
Show glycosyltransferases
There is only one chemically distinct structure:
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