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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: cystic fibrosis (CF) [ICD11: CA25

]; pneumonia [ICD11: CA40

]

NCBI PubMed ID: 22763039
Publication DOI: 10.1093/glycob/cws105
Journal NLM ID: 9104124
Publisher: IRL Press at Oxford University Press
Correspondence: A.S. <silipo

unina.it>; A.I. <imberty

cermav.cnrs.fr>
Institutions: Dipartimento di Scienze Chimiche, Universita di Napoli 'Federico II', Napoli, Italy

Bacteria from the Burkholderia cepacia complex (Bcc) cause highly contagious pneumonia among cystic fibrosis (CF) patients. Among them, Burkholderia cenocepacia is one of the most dangerous in the Bcc and is the most frequent cause of morbidity and mortality in CF patients. Indeed, it is responsible of 'cepacia syndrome', a deadly exacerbation of infection, that is the main cause of poor outcomes in lung transplantation. B. cenocepacia produces several soluble lectins with specificity for fucosylated and mannosylated glycoconjugates. These lectins are present on the bacterial cell surface and it has been proposed that they bind to lipopolysaccharide epitopes. In this work, we report on the interaction of one B. cenocepacia lectin, BC2L-A, with heptose and other manno configured sugar residues. Saturation Transfer Difference (STD) NMR spectroscopy studies of BC2L-A with different mono- and disaccharides demonstrated the requirement of manno configuration with hydroxyl or glycol group at C6 for the binding process. The crystal structure of BC2L-A complexed with the methyl-heptoside confirmed the location of the carbohydrate ring in the binding site and elucidated the orientation of the glycol tail, in agreement with NMR data. Titration calorimetry performed on monosaccharides, heptose disaccharides and bacterial heptose-containing oligosaccharides and polysaccharides confirmed that bacterial cell wall contains carbohydrate epitopes that can bind to BC2L-A. Additionally, the specific binding of fluorescent BC2L-A lectin on B. cenocepacia bacterial surface was demonstrated by electron microscopy.

Lipopolysaccharide, NMR, heptose, bacterial lectin, titration microcalorimetry

Structure type: oligomer
Location inside paper: p.1390, scheme 1, oligosaccharide 2
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_130650,IEDB_130670,IEDB_135607,IEDB_135609,IEDB_136105,IEDB_137473,IEDB_1391961,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141582,IEDB_141584,IEDB_142488,IEDB_146664,IEDB_153207,IEDB_2189047,IEDB_225177,IEDB_226811,IEDB_885822,IEDB_885823,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, X-ray, STD NMR, microcalorimetry, crystallization
Biological activity: binding of the lectin BC2L-A to surfaces of B. cenocepacia
3D data: 3D data

Related record ID(s): 27245, 28450, 28451, 28452, 28453
NCBI Taxonomy refs (TaxIDs): 87883
Reference(s) to other database(s): GTC:G03152EV
Show glycosyltransferases

There is only one chemically distinct structure:

CC(=O)N[C@H]1[C@H](O[C@@H]2[C@@H](O)[C@H](C)O[C@@H](O[C@H]3[C@@H](O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O[C@@H]5O[C@H](CO)[C@H](O)[C@H](O[C@H]6O[C@H](CO)[C@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H]6NC(C)=O)[C@H]5NC(C)=O)[C@H]4O)[C@H](O)[C@@H]([C@@H](O)CO[C@H]4O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]4O)O[C@@H]3O[C@@H]3[C@H](O)[C@@H](O[C@@H]4[C@H](O[C@@]5(C(=O)O)O[C@H]([C@H](O)CO)[C@H](O)[C@H](O)[C@@H]5O)C[C@](O)(C(=O)O)O[C@@H]4[C@H](O)CO)O[C@H]([C@@H](O)CO)[C@H]3O[C@@H]3O[C@H](CO[C@H]4O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]4O)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]2O)O[C@H](C)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize