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

]

NCBI PubMed ID: 22209378
Publication DOI: 10.1016/j.carres.2011.12.007
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: ebedini

unina.it (E. Bedini)
Institutions: Dipartimento di Chimica Organica e Biochimica, Universita di Napoli 'Federico II', Complesso Universitario Monte S.Angelo, Via Cintia 4, 80126 Napoli, Italy

The synthesis of β-Gal-(1→3)-α-GalNAc-(1→3)-β-GalNAc allyl trisaccharide as the outer core fragment of Burkholderia cepacia pv. vietnamiensis lipooligosaccharide was accomplished through a concise, optimized, multi-step synthesis, having as key steps three glycosylations, that were in-depth studied performing them under several conditions. The target trisaccharide was designed with an allyl aglycone in order to open a future access to the conjugation with an immunogenic protein en route to the development of a synthetic neoglycoconjugate vaccine against this Burkholderia pathogen.

Burkholderia cepacia, trisaccharide, galactose, glycosylation, N-acetyl-galactosamine, orthoester

Structure type: oligomer
Location inside paper: p.25, fig.1
Aglycon: lipid A
Compound class: LOS
Contained glycoepitopes: IEDB_130648,IEDB_130650,IEDB_130670,IEDB_134627,IEDB_135607,IEDB_135609,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_137473,IEDB_1391961,IEDB_1391963,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_142488,IEDB_143260,IEDB_146664,IEDB_153207,IEDB_190606,IEDB_2189047,IEDB_225177,IEDB_226811,IEDB_885822,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_23,SB_24,SB_7,SB_8,SB_88

Methods: 13C NMR, 1H NMR, TLC, MALDI-MS, glycosylation, conjugation, chemical synthesis methods
Synthetic data: chemical

Related record ID(s): 28308
NCBI Taxonomy refs (TaxIDs): 60552
Reference(s) to other database(s): GTC:G08282ML
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]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@@H](O[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](O)[C@H](O)[C@H]3O)O[C@H]([C@@H](O)CO[C@H]3O[C@H]([C@@H](O)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](CO)[C@H](O)[C@@H]1O[C@H]1O[C@H](CO)[C@H](O)[C@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H]1NC(C)=O

SVG MW SMILES 3D mol Ionize