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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: acute otitis media [ICD11: AB00

, Life stage: adult]; chronic respiratory tract infections [ICD11: CA45

, ICD11: CB7Z

]; infection due to Haemophilus influenzae [ICD11: XN1P6

]

The structure was elucidated in this paper
NCBI PubMed ID: 21683945
Publication DOI: 10.1016/j.carres.2011.05.020
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: E.K.H. Schweda <Elke.Schweda

ki.se>
Institutions: Karolinska Institutet, Clinical Research Centre, Huddinge, Sweden

The structure of lipopolysaccharide (LPS) expressed by non-typeable Haemophilus influenzae (NTHi) strains 1008 and 1247 has been investigated by mass spectrometry and NMR analyses on O-deacylated LPS and core oligosaccharide material. Both strains express the conserved triheptosyl inner core, [L-α-D-Hepp-(1→2)-[PEtn→6]-L-α-D-Hepp-(1→3)-L-α-D-Hepp-(1→5)-[PPEtn→4]-α-Kdo-(2→6)-Lipid A] with PCho→6)-β-D-Glcp (GlcI) substituting the proximal heptose (HepI) at O-4. Strain 1247 expresses the common structural motifs of H. influenzae; globotetraose [β-D-GalpNAc-(1→3)-α-D-Galp-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→] and its truncated versions globoside [α-D-Galp-(1→4)-β-D-Galp-(1→4)-β-D-Glcp-(1→] and lactose [β-D-Galp-(1→4)-β-D-Glcp-(1→] linked to the terminal heptose of the inner core and GlcI. A genetically distinct NTHi strain, 1008, expresses identical structures to strain 1247 with the exception that it lacks GalNAc. A lpsA mutant of strain 1247 expressed LPS of reduced complexity that facilitated unambiguous structural determination of the oligosaccharide from HepI. By CE-ESI-MS/MS we identified disialylated glycoforms indicating disialyllactose [α-Neu5Ac-(2→8)-α-Neu5Ac-(2→3)-β-D-Gal-(1→4)-β-D-Glcp-(1→] as an extension from GlcI which is a novel finding for NTHi LPS.

Lipopolysaccharide, Haemophilus influenzae, otitis media, Digalactoside, disialyllactoside

Structure type: oligomer
Location inside paper: p.1892, table 6, p.1894, fig.4
Trivial name: disialylated glycoform
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130651,IEDB_130676,IEDB_130679,IEDB_136044,IEDB_136794,IEDB_136906,IEDB_137338,IEDB_137472,IEDB_137473,IEDB_137779,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140624,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_150933,IEDB_150937,IEDB_151528,IEDB_152217,IEDB_153198,IEDB_153199,IEDB_190606,IEDB_2189047,IEDB_241118,IEDB_423106,IEDB_742247,IEDB_858580,IEDB_983931,SB_116,SB_165,SB_166,SB_167,SB_170,SB_171,SB_172,SB_178,SB_187,SB_192,SB_195,SB_21,SB_31,SB_35,SB_37,SB_39,SB_42,SB_6,SB_61,SB_62,SB_68,SB_7,SB_76,SB_84,SB_88

Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, HF solvolysis, ESI-MS, mild acid hydrolysis, de-O-acylation with hydrazine, composition analysis, NMR-1D, alkaline deacylation, HPAEC-PAD, CE-ESI-MS/MS, CE-ESI-MS, LC-ESI-MS
Comments, role: disialylated glycoform from mutant strain H. influenzae (NTHi) 1247lpsA

Related record ID(s): 26977, 26993, 26994, 26995
NCBI Taxonomy refs (TaxIDs): 727
Show glycosyltransferases

There are 10 chemically distinct structures. Please, select:

[1*]O[C@H]1O[C@H]([C@@H](O)CO)[C@@H](O[C@@H]2O[C@H](COP(=O)(O)OCC[N+](C)(C)C)[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O[C@@H]4O[C@H](CO)[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]6NC(C)=O)[C@H]5O)[C@H](O[C@]5(C(=O)O)C[C@H](O)[C@@H](NC(C)=O)[C@H]([C@H](O)[C@@H](CO)O[C@]6(C(=O)O)C[C@H](O)[C@@H](NC(C)=O)[C@H]([C@H](O)[C@H](O)CO)O6)O5)[C@H]4O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2OC(C)=O)[C@H](O[C@H]2O[C@H]([C@H](CO)OP(=O)(O)OCCN)[C@@H](O)[C@H](O)[C@@H]2O[C@H]2O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]2OC(C)=O)[C@@H]1O

SVG MW SMILES 3D mol Ionize

R1 = x?Sug?, Sug = anhKdo-ol