CSDB: Search results

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

, Life stage: adult]; infection due to Haemophilus influenzae [ICD11: XN1P6

]

The structure was elucidated in this paper
NCBI PubMed ID: 17725645
Publication DOI: 10.1111/j.1742-4658.2007.06011.x
Journal NLM ID: 101229646
Publisher: Blackwell Publishing
Correspondence: Elke.Schweda

crc.ki.se
Institutions: Clinical Research Centre, Karolinska Institutet and University College of South Stockholm, Huddinge, Sweden

We report the novel pattern of lipopolysaccharide (LPS) expressed by two disease-associated nontypeable Haemophilus influenzae strains, 1268 and 1200. The strains express 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] and its truncated versions globoside [α-D-Galp-(1→4)-β-D-Galp-(1→4)-β-D-Glcp] and lactose [β-D-Galp-(1→4)-β-D-Glcp] linked to the terminal heptose (HepIII) and the corresponding structures with an α-D-Glcp as the reducing sugar linked to the middle heptose (HepII) in the same LPS molecule. Previously these motifs had been found linked only to either the proximal heptose (HepI) or HepIII of the triheptosyl inner-core moiety 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. This novel finding was obtained by structural studies of LPS using NMR techniques and ESI-MS on O-deacylated LPS and core oligosaccharide material, as well as electrospray ionization-multiple-step tandem mass spectrometry on permethylated dephosphorylated oligosaccharide material. A lpsA mutant of strain 1268 expressed LPS of reduced complexity that facilitated unambiguous structural determination. Using capillary electrophoresis-ESI-MS/MS we identified sialylated glycoforms that included sialyllactose as an extension from HepII, this is a further novel finding for H. influenzae LPS. In addition, each LPS was found to carry phosphocholine and O-linked glycine. Nontypeable H. influenzae strain 1200 expressed identical LPS structures to 1268 with the difference that strain 1200 LPS had acetates substituting HepIII, whereas strain 1268 LPS has glycine at the same position.

Lipopolysaccharide, Haemophilus influenzae, globotetraose, sialyllactose, globoside

Structure type: oligomer
Location inside paper: p.4898, fig.8
Aglycon: lipid A
Trivial name: glycoform
Compound class: LOS
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_1391964,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140624,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_151528,IEDB_152217,IEDB_190606,IEDB_2189047,IEDB_241118,IEDB_423106,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_21,SB_31,SB_6,SB_62,SB_7,SB_88

Methods: 13C NMR, methylation, GLC-MS, NMR-2D, HF solvolysis, mild acid hydrolysis, NMR-1D, genetic methods, alkaline hydrolysis, CE-ESI-MS
Biosynthesis and genetic data: genetic data
Comments, role: NTHi strains 1268 and 1200

Related record ID(s): 21512, 21881
NCBI Taxonomy refs (TaxIDs): 727
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](CO)O[C@H](O[C@H]3[C@@H](CO)O[C@@H](O[C@@H]4[C@@H](CO)O[C@@H](O[C@H]5[C@@H](O)[C@H](O)[C@@H]([C@@H](O)CO)O[C@@H]5O[C@H]5[C@@H](O[C@H]6O[C@H](COP(=O)(O)OCC[N+](C)(C)C)[C@@H](O[C@@H]7O[C@H](CO)[C@H](O[C@H]8O[C@H](CO)[C@H](O)[C@H](O[C@@H]9O[C@H](CO)[C@H](O)[C@H](O)[C@H]9NC(C)=O)[C@H]8O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O)[C@@H]([C@H](CO)OCCN)O[C@@H]5O[C@@H]5[C@H](O)[C@@H](O[C@@H]6[C@H](OP(=O)(O)OP(=O)(O)OCCN)C[C@](O)(C(=O)O)O[C@@H]6[C@H](O)CO)O[C@H]([C@@H](O)CO)[C@H]5O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@@H]2O)O[C@H](CO)[C@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize