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 paperNCBI PubMed ID: 21571259Publication DOI: 10.1016/j.carres.2011.04.030Journal NLM ID: 0043535Publisher: 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: p.1242, fig.1
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_144998,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: LPS from NTHi strain 2019lex2.
Related record ID(s): 26189, 26612, 26613
NCBI Taxonomy refs (TaxIDs): 727Reference(s) to other database(s): GTC:G25638ZI
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7
5,3,2,2 bDGlcp 102.3 73.9 76.3 73.6 76.5 62.7
5,3,2,3,0 xXEtN 62.5 40.4
5,3,2,3 P
5,3,2 aXLDmanHepp 101.6 78.8 70.8 ? ? ? ?
5,3,3,4,4 bDGalp 102.5 76.5 72.0 68.8 74.9 ?
5,3,3,4 bDGlcp 102.5 73.3 74.7 79.0 74.7 60.0
5,3,3 aDGlcp 100.2 72.7 71.7 76.4 71.7 ?
5,3,6,0 xXEtN 61.5 40.4
5,3,6 P
5,3 aXLDmanHepp 98.2 79.3 78.7 ? 74.7 ? ?
5,4 bDGlcp 102.4 73.9 77.2 70.4 77.0 62.7
5 aXLDmanHepp 98.1 70.9 72.5 72.2 ? 69.8 ?
4,0,0 xXEtN
4,0 P
4 P
aXKdop
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7
5,3,2,2 bDGlcp 4.42 3.34 3.46 3.50 3.46 3.75-3.91
5,3,2,3,0 xXEtN 4.29 3.37
5,3,2,3 P
5,3,2 aXLDmanHepp 5.11 4.04 3.98 ? ? ? ?
5,3,3,4,4 bDGalp 4.46 3.54 3.69 3.94 3.69 ?
5,3,3,4 bDGlcp 4.58 3.40 3.68 3.70 3.68 3.84-4.00
5,3,3 aDGlcp 5.32 3.61 3.87 3.66 3.89 ?
5,3,6,0 xXEtN 4.24 3.31
5,3,6 P
5,3 aXLDmanHepp 5.85 4.26 4.11 ? ? 4.62 ?
5,4 bDGlcp 4.55 3.32 3.47 3.43 3.47 3.74-3.93
5 aXLDmanHepp 5.11 4.05 4.04 4.10 ? 4.34 ?
4,0,0 xXEtN
4,0 P
4 P
aXKdop
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7
5,3,2,2 bDGlcp 102.3/4.42 73.9/3.34 76.3/3.46 73.6/3.50 76.5/3.46 62.7/3.75-3.91
5,3,2,3,0 xXEtN 62.5/4.29 40.4/3.37
5,3,2,3 P
5,3,2 aXLDmanHepp 101.6/5.11 78.8/4.04 70.8/3.98 ?/? ?/? ?/? ?/?
5,3,3,4,4 bDGalp 102.5/4.46 76.5/3.54 72.0/3.69 68.8/3.94 74.9/3.69 ?/?
5,3,3,4 bDGlcp 102.5/4.58 73.3/3.40 74.7/3.68 79.0/3.70 74.7/3.68 60.0/3.84-4.00
5,3,3 aDGlcp 100.2/5.32 72.7/3.61 71.7/3.87 76.4/3.66 71.7/3.89 ?/?
5,3,6,0 xXEtN 61.5/4.24 40.4/3.31
5,3,6 P
5,3 aXLDmanHepp 98.2/5.85 79.3/4.26 78.7/4.11 ?/? 74.7/? ?/4.62 ?/?
5,4 bDGlcp 102.4/4.55 73.9/3.32 77.2/3.47 70.4/3.43 77.0/3.47 62.7/3.74-3.93
5 aXLDmanHepp 98.1/5.11 70.9/4.05 72.5/4.04 72.2/4.10 ?/? 69.8/4.34 ?/?
4,0,0 xXEtN
4,0 P
4 P
aXKdop
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 |
|---|
| 5,3,2,2 | bDGlcp | 4.42 | 3.34 | 3.46 | 3.50 | 3.46 | 3.75
3.91 | |
| 5,3,2,3,0 | xXEtN | 4.29 | 3.37 | |
| 5,3,2,3 | P | |
| 5,3,2 | aXLDmanHepp | 5.11 | 4.04 | 3.98 | ? | ? | ? | ? |
| 5,3,3,4,4 | bDGalp | 4.46 | 3.54 | 3.69 | 3.94 | 3.69 | ? | |
| 5,3,3,4 | bDGlcp | 4.58 | 3.40 | 3.68 | 3.70 | 3.68 | 3.84
4.00 | |
| 5,3,3 | aDGlcp | 5.32 | 3.61 | 3.87 | 3.66 | 3.89 | ? | |
| 5,3,6,0 | xXEtN | 4.24 | 3.31 | |
| 5,3,6 | P | |
| 5,3 | aXLDmanHepp | 5.85 | 4.26 | 4.11 | ? | ? | 4.62 | ? |
| 5,4 | bDGlcp | 4.55 | 3.32 | 3.47 | 3.43 | 3.47 | 3.74
3.93 | |
| 5 | aXLDmanHepp | 5.11 | 4.05 | 4.04 | 4.10 | ? | 4.34 | ? |
| 4,0,0 | xXEtN | |
| 4,0 | P | |
| 4 | P | |
| | aXKdop | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 |
|---|
| 5,3,2,2 | bDGlcp | 102.3 | 73.9 | 76.3 | 73.6 | 76.5 | 62.7 | |
| 5,3,2,3,0 | xXEtN | 62.5 | 40.4 | |
| 5,3,2,3 | P | |
| 5,3,2 | aXLDmanHepp | 101.6 | 78.8 | 70.8 | ? | ? | ? | ? |
| 5,3,3,4,4 | bDGalp | 102.5 | 76.5 | 72.0 | 68.8 | 74.9 | ? | |
| 5,3,3,4 | bDGlcp | 102.5 | 73.3 | 74.7 | 79.0 | 74.7 | 60.0 | |
| 5,3,3 | aDGlcp | 100.2 | 72.7 | 71.7 | 76.4 | 71.7 | ? | |
| 5,3,6,0 | xXEtN | 61.5 | 40.4 | |
| 5,3,6 | P | |
| 5,3 | aXLDmanHepp | 98.2 | 79.3 | 78.7 | ? | 74.7 | ? | ? |
| 5,4 | bDGlcp | 102.4 | 73.9 | 77.2 | 70.4 | 77.0 | 62.7 | |
| 5 | aXLDmanHepp | 98.1 | 70.9 | 72.5 | 72.2 | ? | 69.8 | ? |
| 4,0,0 | xXEtN | |
| 4,0 | P | |
| 4 | P | |
| | aXKdop | |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":102.3,"l":"1","c":[0,0,225]},{"s":73.9,"l":"2","c":[0,0,225]},{"s":76.3,"l":"3","c":[0,0,225]},{"s":73.6,"l":"4","c":[0,0,225]},{"s":76.5,"l":"5","c":[0,0,225]},{"s":62.7,"l":"6","c":[0,0,225]},{"s":62.5,"l":"1","c":[230,0,30]},{"s":40.4,"l":"2","c":[230,0,30]},{"s":101.6,"l":"1","c":[0,165,0]},{"s":78.8,"l":"2","c":[0,165,0]},{"s":70.8,"l":"3","c":[0,165,0]},{"s":102.5,"l":"1","c":[120,0,225]},{"s":76.5,"l":"2","c":[120,0,225]},{"s":72,"l":"3","c":[120,0,225]},{"s":68.8,"l":"4","c":[120,0,225]},{"s":74.9,"l":"5","c":[120,0,225]},{"s":102.5,"l":"1","c":[0,192,255]},{"s":73.3,"l":"2","c":[0,192,255]},{"s":74.7,"l":"3","c":[0,192,255]},{"s":79,"l":"4","c":[0,192,255]},{"s":74.7,"l":"5","c":[0,192,255]},{"s":60,"l":"6","c":[0,192,255]},{"s":100.2,"l":"1","c":[220,0,180]},{"s":72.7,"l":"2","c":[220,0,180]},{"s":71.7,"l":"3","c":[220,0,180]},{"s":76.4,"l":"4","c":[220,0,180]},{"s":71.7,"l":"5","c":[220,0,180]},{"s":61.5,"l":"1","c":[100,160,0]},{"s":40.4,"l":"2","c":[100,160,0]},{"s":98.2,"l":"1","c":[210,210,0]},{"s":79.3,"l":"2","c":[210,210,0]},{"s":78.7,"l":"3","c":[210,210,0]},{"s":74.7,"l":"5","c":[210,210,0]},{"s":102.4,"l":"1","c":[210,110,0]},{"s":73.9,"l":"2","c":[210,110,0]},{"s":77.2,"l":"3","c":[210,110,0]},{"s":70.4,"l":"4","c":[210,110,0]},{"s":77,"l":"5","c":[210,110,0]},{"s":62.7,"l":"6","c":[210,110,0]},{"s":98.1,"l":"1","c":[90,45,15]},{"s":70.9,"l":"2","c":[90,45,15]},{"s":72.5,"l":"3","c":[90,45,15]},{"s":72.2,"l":"4","c":[90,45,15]},{"s":69.8,"l":"6","c":[90,45,15]}])
The spectrum also has 11 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
