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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: Sus scrofa
Associated disease: polyserositis [ICD11: 4A60.0

]

The structure was elucidated in this paper
NCBI PubMed ID: 23664728
Publication DOI: 10.1016/j.carres.2013.04.023
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: E. Vinogradov <Evguenii.Vinogradov

nrc-cnrc.gc.ca>
Institutions: National Research Council, Ottawa, ON, Canada, Faculté de médecine vétérinaire, Université de Montréal, St-Hyacinthe, Québec, Canada, Centre de Recerca en Sanitat Animal (CReSA), UAB-IRTA, Campus de la Universitat Autònoma de Barcelona, Bellaterra (Cerdanyola del Vallès) and Institut de Recerca i Tecnología Agroalimentàries (IRTA), Barcelona, Spain

Haemophilus parasuis is a Gram-negative bacterium from the family Pasteurellaceae and a swine pathogen. H. parasuis is found in the upper respiratory tract of piglets and produces Glasser's disease, an invasive disease characterized by polyserositis. H. parasuis contains a short lipopolysaccharide (LPS) or lipooligosaccharide (LOS) reported to play a partial role in interaction with host cells. The presence of capsule has been phenotypically demonstrated in certain H. parasuis strains and its role in virulence has been suggested, but the chemical structure of the surface polysaccharides of this bacterium was unknown. The structure of capsular polysaccharide (CPS) and LOS from virulent strains ER-6P and Nagasaki was studied by NMR spectroscopy, mass spectrometry and chemical methods. CPS from both strains had the same main chain with disaccharide repeating unit, substituted with α-Neu5R-(2-3)-α-GalNAc-(1-P-(strain ER-6P) or α-Neu5R-(2-3)-α-Gal-(1-P-strain Nagasaki) side chains, where R is the N-acetyl or N-glycolyl group. Glycolyl-neuraminic acid is widely found in animal glycoproteins, but it apparently has not been found in bacteria before, and might be important for the biology of this microorganism. Ac and Gc were present in equal amounts in the strain ER-6P but Nagasaki contained only about 20% of Gc substituent. Both strains produced the same LPS of a rough type with a single phosphorylated Kdo linking core and lipid A parts. LOS structure was similar to some strains of H. influenzae and contained a globotetraose terminal sequence.

Lipopolysaccharide, polysaccharide, capsule, Haemophilus parasuis

Structure type: oligomer
Location inside paper: p.94, fig.4, 6
Compound class: LPS
Contained glycoepitopes: IEDB_130650,IEDB_130651,IEDB_135394,IEDB_136044,IEDB_136906,IEDB_137338,IEDB_137472,IEDB_137473,IEDB_137777,IEDB_1391964,IEDB_140088,IEDB_140956,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152217,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_423106,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_31,SB_6,SB_62,SB_7,SB_88

Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, ESI-MS, mild acid hydrolysis, alkaline degradation, GC, de-O-acylation with hydrazine, NMR-1D, methanolysis, CE-MS
Comments, role: completely deacylated LPS. Published NMR assignment of Kdo C6 (81.1) is erroneous.

Related record ID(s): 29316, 29718, 29719, 29720, 29721, 29722, 29723
NCBI Taxonomy refs (TaxIDs): 1117322, 738
Show glycosyltransferases

NMR conditions: in D2O / H2O at 298 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
0,6,6,5,3,2	aXDDmanHepp	103.2	72.0	72.2	67.9	73.2	71.0	65.1
0,6,6,5,3	aXLDmanHepp	101.7	80.6	71.7	68.1	75.6	70.4	64.8
0,6,6,5,4,4,4,4,4,3	bDGalpN	102.2	55.3	73.2	69.2	77.0	62.4
0,6,6,5,4,4,4,4,4	aDGalp	101.9	69.3	80.3	70.6	72.0	62.1
0,6,6,5,4,4,4,4	bDGalp	104.8	72.5	72.5	73.8	77.1	62.0
0,6,6,5,4,4,4	bDGlcp	104.0	74.6	75.6	79.9	76.3	61
0,6,6,5,4,4	bDGlcp	104.0	74.6	75.6	79.7	76.3	61.5
0,6,6,5,4	aDGlcp	103.8	75.0	76.3	79.9	76.3	61.5
0,6,6,5,6	aDGlcp	102.4	73.7	74.6	70.5	73.4	61.5
0,6,6,5	aXLDmanHepp	101.2	71.8	76.4	75.7	73.4	81.1	64.1
0,6,6,4	P
0,6,6	?XKdop	?	?	35.5	71.7	73.7	?	70.9	65.1
0,6,4	P
0,6	bDGlcpN	100.6	57.1	73.3	75.8	75.3	64.0
0	aDGlcpN	93.4	55.6	71.0	71.2	74.2	70.6
	P


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
0,6,6,5,3,2	aXDDmanHepp	5.30	3.97	3.87	3.82	3.78	4.03	3.72-3.75
0,6,6,5,3	aXLDmanHepp	5.53	4.30	3.97	3.91	3.65	4.05	3.64-3.74
0,6,6,5,4,4,4,4,4,3	bDGalpN	4.93	3.30	3.92	3.99	3.76	3.79
0,6,6,5,4,4,4,4,4	aDGalp	4.98	4.05	4.12	4.30	4.41	3.71
0,6,6,5,4,4,4,4	bDGalp	4.52	3.59	3.59	3.75	3.79	3.86-3.93
0,6,6,5,4,4,4	bDGlcp	4.54	3.36	3.66	3.68	3.64	3.83-3.99
0,6,6,5,4,4	bDGlcp	4.58	3.36	3.66	3.71	3.60	3.84-3.94
0,6,6,5,4	aDGlcp	4.68	3.46	3.63	3.68	3.54	3.94-4.00
0,6,6,5,6	aDGlcp	5.23	3.57	3.83	3.51	3.95	3.87-3.92
0,6,6,5	aXLDmanHepp	5.16	4.15	4.10	4.20	4.21	4.20	3.92-4.00
0,6,6,4	P
0,6,6	?XKdop	-	-	2.08-2.35	4.61	4.30	4.20	3.80	3.76-3.95
0,6,4	P
0,6	bDGlcpN	4.88	3.16	3.90	3.93	3.77	3.60-3.76
0	aDGlcpN	5.74	3.46	3.93	3.53	4.12	3.90-4.29
	P


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8
0,6,6,5,3,2	aXDDmanHepp	103.2/5.30	72.0/3.97	72.2/3.87	67.9/3.82	73.2/3.78	71.0/4.03	65.1/3.72-3.75
0,6,6,5,3	aXLDmanHepp	101.7/5.53	80.6/4.30	71.7/3.97	68.1/3.91	75.6/3.65	70.4/4.05	64.8/3.64-3.74
0,6,6,5,4,4,4,4,4,3	bDGalpN	102.2/4.93	55.3/3.30	73.2/3.92	69.2/3.99	77.0/3.76	62.4/3.79
0,6,6,5,4,4,4,4,4	aDGalp	101.9/4.98	69.3/4.05	80.3/4.12	70.6/4.30	72.0/4.41	62.1/3.71
0,6,6,5,4,4,4,4	bDGalp	104.8/4.52	72.5/3.59	72.5/3.59	73.8/3.75	77.1/3.79	62.0/3.86-3.93
0,6,6,5,4,4,4	bDGlcp	104.0/4.54	74.6/3.36	75.6/3.66	79.9/3.68	76.3/3.64	61/3.83-3.99
0,6,6,5,4,4	bDGlcp	104.0/4.58	74.6/3.36	75.6/3.66	79.7/3.71	76.3/3.60	61.5/3.84-3.94
0,6,6,5,4	aDGlcp	103.8/4.68	75.0/3.46	76.3/3.63	79.9/3.68	76.3/3.54	61.5/3.94-4.00
0,6,6,5,6	aDGlcp	102.4/5.23	73.7/3.57	74.6/3.83	70.5/3.51	73.4/3.95	61.5/3.87-3.92
0,6,6,5	aXLDmanHepp	101.2/5.16	71.8/4.15	76.4/4.10	75.7/4.20	73.4/4.21	81.1/4.20	64.1/3.92-4.00
0,6,6,4	P
0,6,6	?XKdop			35.5/2.08-2.35	71.7/4.61	73.7/4.30	?/4.20	70.9/3.80	65.1/3.76-3.95
0,6,4	P
0,6	bDGlcpN	100.6/4.88	57.1/3.16	73.3/3.90	75.8/3.93	75.3/3.77	64.0/3.60-3.76
0	aDGlcpN	93.4/5.74	55.6/3.46	71.0/3.93	71.2/3.53	74.2/4.12	70.6/3.90-4.29
	P

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
0,6,6,5,3,2	aXDDmanHepp	5.30	3.97	3.87	3.82	3.78	4.03	3.72 3.75
0,6,6,5,3	aXLDmanHepp	5.53	4.30	3.97	3.91	3.65	4.05	3.64 3.74
0,6,6,5,4,4,4,4,4,3	bDGalpN	4.93	3.30	3.92	3.99	3.76	3.79
0,6,6,5,4,4,4,4,4	aDGalp	4.98	4.05	4.12	4.30	4.41	3.71
0,6,6,5,4,4,4,4	bDGalp	4.52	3.59	3.59	3.75	3.79	3.86 3.93
0,6,6,5,4,4,4	bDGlcp	4.54	3.36	3.66	3.68	3.64	3.83 3.99
0,6,6,5,4,4	bDGlcp	4.58	3.36	3.66	3.71	3.60	3.84 3.94
0,6,6,5,4	aDGlcp	4.68	3.46	3.63	3.68	3.54	3.94 4.00
0,6,6,5,6	aDGlcp	5.23	3.57	3.83	3.51	3.95	3.87 3.92
0,6,6,5	aXLDmanHepp	5.16	4.15	4.10	4.20	4.21	4.20	3.92 4.00
0,6,6,4	P
0,6,6	?XKdop			2.08 2.35	4.61	4.30	4.20	3.80	3.76 3.95
0,6,4	P
0,6	bDGlcpN	4.88	3.16	3.90	3.93	3.77	3.60 3.76
0	aDGlcpN	5.74	3.46	3.93	3.53	4.12	3.90 4.29
	P

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
0,6,6,5,3,2	aXDDmanHepp	103.2	72.0	72.2	67.9	73.2	71.0	65.1
0,6,6,5,3	aXLDmanHepp	101.7	80.6	71.7	68.1	75.6	70.4	64.8
0,6,6,5,4,4,4,4,4,3	bDGalpN	102.2	55.3	73.2	69.2	77.0	62.4
0,6,6,5,4,4,4,4,4	aDGalp	101.9	69.3	80.3	70.6	72.0	62.1
0,6,6,5,4,4,4,4	bDGalp	104.8	72.5	72.5	73.8	77.1	62.0
0,6,6,5,4,4,4	bDGlcp	104.0	74.6	75.6	79.9	76.3	61
0,6,6,5,4,4	bDGlcp	104.0	74.6	75.6	79.7	76.3	61.5
0,6,6,5,4	aDGlcp	103.8	75.0	76.3	79.9	76.3	61.5
0,6,6,5,6	aDGlcp	102.4	73.7	74.6	70.5	73.4	61.5
0,6,6,5	aXLDmanHepp	101.2	71.8	76.4	75.7	73.4	81.1	64.1
0,6,6,4	P
0,6,6	?XKdop	?	?	35.5	71.7	73.7	?	70.9	65.1
0,6,4	P
0,6	bDGlcpN	100.6	57.1	73.3	75.8	75.3	64.0
0	aDGlcpN	93.4	55.6	71.0	71.2	74.2	70.6
	P

The spectrum also has 3 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

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](CO)O[C@@H](O[C@@H]6[C@@H](CO)O[C@H](O[C@@H]7[C@@H]([C@H](CO)O[C@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)O[C@H](O[C@@H]8[C@H](OP(=O)(O)O)CC(OC[C@H]9O[C@@H](OC[C@H]%10O[C@H](OP(=O)(O)O)[C@H](N)[C@@H](O)[C@@H]%10O)[C@H](N)[C@@H](O)[C@@H]9OP(=O)(O)O)(C(=O)O)O[C@@H]8[C@H](O)CO)[C@@H](O)[C@H]7O[C@H]7O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]7O[C@H]7O[C@H]([C@H](O)CO)[C@@H](O)[C@H](O)[C@@H]7O)[C@H](O)[C@H]6O)[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