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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: meningitis [ICD11: 1D01

]; septicemia [ICD11: MA15.Y

]; 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: 21571259
Publication DOI: 10.1016/j.carres.2011.04.030
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: E.K.H. Schweda <Elke.Schweda

ki.se>
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada K1A OR6, Clinical Research Centre, University College of South Stockholm, Karolinska Institutet, Stockholm, NOVUM, S-141 86 Huddinge, Sweden, Molecular Infectious Diseases Group, University of Oxford Department of Paediatrics, Weatherall Institute of Molecular Medicine, John Radcliffe Hospital, Headington, Oxford 0X3 9DS, UK

We have investigated the structure of the lipopolysaccharide (LPS) of nontypeable Haemophilus influenzae (NTHi) strain 2019, a prototype strain that is used for studies of NTHi biology and disease. Analysis of LPS from wild type and lex2B, lpt3 and pgm mutant strains using NMR techniques and ESI-MS on O-deacylated LPS and core oligosaccharide material (OS), as well as ESI-MS(n) on permethylated dephosphorylated OS, confirmed the previously established structure in which lactose is linked to the proximal heptose (HepI) of the conserved 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. Importantly, our data provide further structural detail whereby extensions from the middle heptose (HepII) are now characterized as β-D-Galp-(1→4)-β-D-Glcp-(1→4)-α-D-Glcp-(1→3 and truncated versions thereof. PEtn substitutes O-3 of the distal heptose (HepIII) of the inner-core moiety. This PEtn substituent was absent in the lpt3 mutant indicating that Lpt3 is the transferase required to add PEtn to the distal heptose. Interestingly, in the lex2B mutant strain HepIII was found to be substituted at O-2 by β-D-Glcp which, in turn, can be further extended. Contrary to previous findings, LPS of the pgm mutant strain contained minor glycoforms having β-D-Glcp linked to O-4 of HepI and also glycoforms with an additional PEtn which could be assigned to HepIII. Acetate groups and one glycine residue further substitute HepIII in NTHi 2019.

Lipopolysaccharide, Haemophilus influenzae, structure analysis, lex2, lex3, pgm

Structure type: oligomer
Location inside paper: abstract, p.1242, fig.1, p.1248
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_136044,IEDB_137472,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88

Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, PCR, sugar analysis, dephosphorylation, 31P NMR, deacylation, ESI-MS, mild acid hydrolysis, de-O-acylation with hydrazine, NMR-1D, genetic methods, HPLC, CE-ESI-MS/MS, Southern blotting, CE-ESI-MS
Comments, role: the glycoform LPS from NTHi strain 2019pgm.

Related record ID(s): 26189, 26611, 26612
NCBI Taxonomy refs (TaxIDs): 727
Reference(s) to other database(s): GTC:G74024GC
Show glycosyltransferases

There is only one chemically distinct structure:

NCCOP(=O)(O)O[C@@H](CO)[C@H]1O[C@H](O[C@@H]2[C@H](O)[C@@H](O[C@@H]3[C@H](OP(=O)(O)OP(=O)(O)OCCN)C[C@](O)(C(=O)O)O[C@@H]3[C@H](O)CO)O[C@H]([C@@H](O)CO)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@@H](O[C@H]2O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](OP(=O)(O)OCCN)[C@@H]2O)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize