Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: pneumonia [ICD11:
CA40 
];
urinary tract infections (UTI) [ICD11:
GC08 ];
liver abscess [ICD11:
DB90.0 , ICD11:
SA04 ];
infection due to Klebsiella pneumoniae [ICD11:
XN741 ]
NCBI PubMed ID: 21478151Publication DOI: 10.1074/jbc.M111.222091Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: kfhua
niu.edu.tw; shwu
gate.sinica.edu.tw
Institutions: Institute of Biological Chemistry, Academia Sinica, Taipei 115, Institute of Biotechnology, National Ilan University, I-Lan 260, Department of Horticulture, National Taiwan University, Taipei 106, Genomics Research Center, Academia Sinica, Taipei 115, Department of Microbiology, National Taiwan University, Taipei 100, Department of Internal Medicine, National Taiwan University Hospital, Taipei 100, Taiwan
The active components of a primary pyrogenic liver abscess (PLA) Klebsiella pneumoniae in stimulating cytokine expression in macrophages are still unclear. The capsular polysaccharide (CPS) of PLA K. pneumoniae is important in determining clinical manifestations, and we have shown that it consists of repeating units of the trisaccharide (→3)-β-D-Glc-(1→4)-[2,3-(S)-pyruvate]-β-D-GlcA-(1→4)-α-L-Fuc-(1→) and has the unusual feature of extensive pyruvation of glucuronic acid and acetylation of C2-OH or C3-OH of fucose. We demonstrated that PLA K. pneumoniae CPS induces secretion of tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) by macrophages through Toll-like receptor 4 (TLR4) and that this effect was lost when pyruvation and O-acetylation were chemically destroyed. Furthermore, expression of TNF-α and IL-6 in PLA K. pneumoniae CPS-stimulated macrophages was shown to be regulated by the TLR4/ROS/PKC-δ/NF-κB, TLR4/PI3-kinase/AKT/NF-κB, and TLR4/MAPK signaling pathways.
capsular polysaccharide, Klebsiella pneumoniae, inflammation, innate immunity, carbohydrate structure, pathogen-associated molecular pattern, Toll-like Receptors (TLR)
Structure type: polymer chemical repeating unit
Location inside paper: p.21044, fig.1D
Compound class: CPS
Contained glycoepitopes: IEDB_115136,IEDB_136045,IEDB_140630,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_146664,IEDB_152214,IEDB_174333,IEDB_423153,IEDB_983931,SB_192,SB_86
Methods: 13C NMR, 1H NMR, NMR-2D, partial acid hydrolysis, GC-MS, sugar analysis, Western blotting, NMR-1D, methanolysis, serological methods, genetic methods, colorimetry, statistical analysis
Biological activity: interaction between TLR4 and PLA K. pneumoniae CPS
Comments, role: the glucuronic acid residue of the trisaccharide repeating unit is pyruvylated to 48-54%. Two different NMR spectra of the pyruvate residue are present in the paper. Error: there is one extra Glc residue in the figure. signals 4 and 5 (75.6 67.8) in the #4,4_bDGlcp 13C NMR spectrum were replaced by ? due to NMR simulation
3D data: molecular modeling
Related record ID(s): 27015
NCBI Taxonomy refs (TaxIDs): 573
Show glycosyltransferases
NMR conditions: in D2O at 300 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,4 bDGlcp 102.1 75.6 81.4 ? ? 60.4
4,3 51%xSPyr 175.3 92.5 25.0
4 bDGlcpA 102.8 73.3 73.8 79.5 74.0 172.8
aLFucp 98.9 68.5 68.7 80.9 66.7 15.0
2 Ac 169.1 26.2
3 Ac 169.1 26.2
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,4 bDGlcp 4.40 3.38 3.48 3.38 3.38 3.62-3.79
4,3 51%xSPyr - - 1.46
4 bDGlcpA 4.44 3.39 3.55 3.72 3.90 -
aLFucp 5.18 3.68 3.76 3.89 4.30 1.14
2 Ac - 2.27
3 Ac - 2.27
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,4 bDGlcp 102.1/4.40 75.6/3.38 81.4/3.48 ?/3.38 ?/3.38 60.4/3.62-3.79
4,3 51%xSPyr 25.0/1.46
4 bDGlcpA 102.8/4.44 73.3/3.39 73.8/3.55 79.5/3.72 74.0/3.90
aLFucp 98.9/5.18 68.5/3.68 68.7/3.76 80.9/3.89 66.7/4.30 15.0/1.14
2 Ac 26.2/2.27
3 Ac 26.2/2.27
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,4 | bDGlcp | 4.40 | 3.38 | 3.48 | 3.38 | 3.38 | 3.62
3.79 |
| 4,3 | 51%xSPyr |
|
| 1.46 | |
| 4 | bDGlcpA | 4.44 | 3.39 | 3.55 | 3.72 | 3.90 |
|
| | aLFucp | 5.18 | 3.68 | 3.76 | 3.89 | 4.30 | 1.14 |
| 2 | Ac |
| 2.27 | |
| 3 | Ac |
| 2.27 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,4 | bDGlcp | 102.1 | 75.6 | 81.4 | ? | ? | 60.4 |
| 4,3 | 51%xSPyr | 175.3 | 92.5 | 25.0 | |
| 4 | bDGlcpA | 102.8 | 73.3 | 73.8 | 79.5 | 74.0 | 172.8 |
| | aLFucp | 98.9 | 68.5 | 68.7 | 80.9 | 66.7 | 15.0 |
| 2 | Ac | 169.1 | 26.2 | |
| 3 | Ac | 169.1 | 26.2 | |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":102.1,"l":"1","c":[0,0,225]},{"s":75.6,"l":"2","c":[0,0,225]},{"s":81.4,"l":"3","c":[0,0,225]},{"s":60.4,"l":"6","c":[0,0,225]},{"s":175.3,"l":"1","c":[230,0,30]},{"s":92.5,"l":"2","c":[230,0,30]},{"s":25,"l":"3","c":[230,0,30]},{"s":102.8,"l":"1","c":[0,165,0]},{"s":73.3,"l":"2","c":[0,165,0]},{"s":73.8,"l":"3","c":[0,165,0]},{"s":79.5,"l":"4","c":[0,165,0]},{"s":74,"l":"5","c":[0,165,0]},{"s":172.8,"l":"6","c":[0,165,0]},{"s":98.9,"l":"1","c":[120,0,225]},{"s":68.5,"l":"2","c":[120,0,225]},{"s":68.7,"l":"3","c":[120,0,225]},{"s":80.9,"l":"4","c":[120,0,225]},{"s":66.7,"l":"5","c":[120,0,225]},{"s":15,"l":"6","c":[120,0,225]},{"s":169.1,"l":"1","c":[0,0,0]},{"s":26.2,"l":"2","c":[0,0,0]},{"s":169.1,"l":"1","c":[0,0,0]},{"s":26.2,"l":"2","c":[0,0,0]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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