Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: cystic fibrosis (CF) [ICD11:
CA25 
]
The structure was elucidated in this paperNCBI PubMed ID: 24933233Publication DOI: 10.1016/j.carres.2014.04.018Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: ebedini
unina.it (E.Bedini)
Institutions: Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S.Angelo, Via Cintia 4, 80126 Napoli, Italy
The first synthesis of the outer core fragment of Burkholderia multivorans lipooligosaccharide [β-D-Glc-(1→3)-α-D-GalNAc-(1→3)-β-D-GalNAc-(1→3)-l-Rha] as alpha-allyl tetrasaccharide was accomplished. The glycosylations involving GalNAc units were studied in depth testing them under several conditions. This allowed the building of both the α- and the β-configured glycosidic bonds by employing the same GalNAc glycosyl donor, thus considerably shortening the total number of synthetic steps. The target tetrasaccharide was synthesized with an allyl aglycone to allow its future conjugation with an immunogenic protein en route to the development of a synthetic neoglycoconjugate vaccine against the Burkholderia cepacia pathogens.
oligosaccharide, Burkholderia cepacia, glucose, rhamnose, glycosylation, N-acetyl-galactosamine
Structure type: oligomer
Location inside paper: p.184, fig.2, p.185, scheme 2, compound 2
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_136105,IEDB_137473,IEDB_1391961,IEDB_141582,IEDB_141584,IEDB_142488,IEDB_146664,IEDB_153207,IEDB_225177,IEDB_885822,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, chemical methods, MALDI-TOF MS, glycosylation, CD
Synthetic data: chemical
Comments, role: Synthetic tetrasaccharide outer core fragment of the B. multivorans LOS.
Related record ID(s): 30699, 30900, 30901, 30902
NCBI Taxonomy refs (TaxIDs): 87883
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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