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Taxonomic group: bacteria / Firmicutes (Phylum: Firmicutes)
Associated disease: septicemia [ICD11: MA15.Y

]; infection due to Streptococcus suis [ICD11: XN5SE

]

The structure was elucidated in this paper
NCBI PubMed ID: 26912653
Publication DOI: 10.1074/jbc.M115.700716
Journal NLM ID: 2985121R
Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: mariela.segura

umontreal.ca
Institutions: From the Food Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, Quebec J2S 8E3, Canada, the Swine and Poultry Infectious Disease Research Centre and the Swine and Poultry Infectious Disease Research Centre and Research Group on Infectious Diseases of Swine, Faculty of Veterinary Medicine, University of Montreal, Saint-Hyacinthe, Quebec J2S 2M2, Canada, the Bacterial and Parasitic Diseases Research Division, National Institute of Animal Health, National Agriculture and Food Research Organization, Tsukuba, Ibaraki 305 0856, Japan, the United Graduate School of Veterinary Sciences, Gifu University, Gifu, Gifu 501 1193, Japan, the Department of Chemistry, Universite du Quebec a Montreal, Montreal, Quebec H3C 3P8, Canada

The capsular polysaccharide (CPS) is a major virulence factor in many encapsulated pathogens, as it is the case for Streptococcus suis, an important swine pathogen and emerging zoonotic agent. Moreover, the CPS is the antigen at the origin of S. suis classification into serotypes. Hence, analyses of the CPS structure are an essential step to dissect its role in virulence and the serological relations between important serotypes. Here, the CPSs of serotypes 1 and 1/2 were purified and characterized for the first time. Chemical and spectroscopic data gave the following repeating unit sequences: [6)[Neu5Ac(α2-6)GalNAc(β1-4)GlcNAc(β1-3)]Gal(β1-3)Gal(β1-4)Glc(β1-]n (serotype 1) and [4)[Neu5Ac(α2-6)GalNAc(β1-4)GlcNAc(β1-3)]Gal(β1-4)[Gal(α1-3)]Rha(β1-4)Glc(β1-]n (serotype 1/2). The Sambucus nigra lectin, which recognizes the Neu5Ac(α2-6)Gal/GalNAc sequence, showed binding to both CPSs. Compared with previously characterized serotype 14 and 2 CPSs, N-acetylgalactosamine replaces galactose as the sugar bearing the sialic acid residue in the side chain. Serological analyses of the cross-reaction of serotype 1/2 with serotypes 1 and 2 and that between serotypes 1 and 14 suggested that the side chain, and more particularly the terminal sialic acid, constitutes one important epitope for serotypes 1/2 and 2. The side chain is also an important serological determinant for serotype 1, yet sialic acid seems to play a limited role. In contrast, the side chain does not seem to be part of a major epitope for serotype 14. These results contribute to the understanding of the relationship between S. suis serotypes and provide the basis for improving diagnostic tools.

polysaccharide, Streptococcus, sialic acid, carbohydrate structure, immunochemistry, chemical biology, Streptococcus suis

Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.8393, scheme 1, p.8395, fig.9A, serotype 1
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_141501,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149155,IEDB_149174,IEDB_151531,IEDB_190606,IEDB_548863,IEDB_548868,IEDB_983931,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_6,SB_7,SB_84,SB_88

Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, GC, NMR-1D, serological methods, UV, SEC, mild acid degradation, enzyme-linked lectin assay

Related record ID(s): 11345, 11769, 11770, 11772
NCBI Taxonomy refs (TaxIDs): 1307
Reference(s) to other database(s): GTC:G11481VZ
Show glycosyltransferases

NMR conditions: in D2O; pH 8 at 338(C), 343(H) K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9
4,3,3,4,6,5	Ac	177.66	24.77
4,3,3,4,6	aXNeup	175.97	103.00	42.86	70.87	54.74	75.30	71.31	74.46	65.56
4,3,3,4,2	Ac	177.30	24.97
4,3,3,4	bDGalpN	104.77	55.24	73.43	70.28	76.42	66.06
4,3,3,2	Ac	177.49	25.08
4,3,3	bDGlcpN	105.14	57.66	75.11	83.54	76.89	63.03
4,3	bDGalp	106.83	72.88	84.49	70.97	75.85	71.47
4	bDGalp	105.30	72.87	84.81	71.06	77.65	63.68
	bDGlcp	105.29	75.54	77.19	81.28	77.51	63.00


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9
4,3,3,4,6,5	Ac	-	2.03
4,3,3,4,6	aXNeup	-	-	1.68-2.68	3.68	3.77	3.71	3.56	3.88	3.65-3.88
4,3,3,4,2	Ac	-	2.06
4,3,3,4	bDGalpN	4.52	3.93	3.74	3.93	3.79	3.61-4.00
4,3,3,2	Ac	-	2.05
4,3,3	bDGlcpN	4.74	3.78	3.78	3.55	3.54	3.64-3.82
4,3	bDGalp	4.62	3.66	3.73	4.13	3.85	3.85-4.02
4	bDGalp	4.49	3.71	3.80	4.17	3.73	3.77
	bDGlcp	4.49	3.33	3.63	3.64	3.58	3.80-3.97


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9
4,3,3,4,6,5	Ac		24.77/2.03
4,3,3,4,6	aXNeup			42.86/1.68-2.68	70.87/3.68	54.74/3.77	75.30/3.71	71.31/3.56	74.46/3.88	65.56/3.65-3.88
4,3,3,4,2	Ac		24.97/2.06
4,3,3,4	bDGalpN	104.77/4.52	55.24/3.93	73.43/3.74	70.28/3.93	76.42/3.79	66.06/3.61-4.00
4,3,3,2	Ac		25.08/2.05
4,3,3	bDGlcpN	105.14/4.74	57.66/3.78	75.11/3.78	83.54/3.55	76.89/3.54	63.03/3.64-3.82
4,3	bDGalp	106.83/4.62	72.88/3.66	84.49/3.73	70.97/4.13	75.85/3.85	71.47/3.85-4.02
4	bDGalp	105.30/4.49	72.87/3.71	84.81/3.80	71.06/4.17	77.65/3.73	63.68/3.77
	bDGlcp	105.29/4.49	75.54/3.33	77.19/3.63	81.28/3.64	77.51/3.58	63.00/3.80-3.97

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9
4,3,3,4,6,5	Ac		2.03
4,3,3,4,6	aXNeup			1.68 2.68	3.68	3.77	3.71	3.56	3.88	3.65 3.88
4,3,3,4,2	Ac		2.06
4,3,3,4	bDGalpN	4.52	3.93	3.74	3.93	3.79	3.61 4.00
4,3,3,2	Ac		2.05
4,3,3	bDGlcpN	4.74	3.78	3.78	3.55	3.54	3.64 3.82
4,3	bDGalp	4.62	3.66	3.73	4.13	3.85	3.85 4.02
4	bDGalp	4.49	3.71	3.80	4.17	3.73	3.77
	bDGlcp	4.49	3.33	3.63	3.64	3.58	3.80 3.97

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9
4,3,3,4,6,5	Ac	177.66	24.77
4,3,3,4,6	aXNeup	175.97	103.00	42.86	70.87	54.74	75.30	71.31	74.46	65.56
4,3,3,4,2	Ac	177.30	24.97
4,3,3,4	bDGalpN	104.77	55.24	73.43	70.28	76.42	66.06
4,3,3,2	Ac	177.49	25.08
4,3,3	bDGlcpN	105.14	57.66	75.11	83.54	76.89	63.03
4,3	bDGalp	106.83	72.88	84.49	70.97	75.85	71.47
4	bDGalp	105.30	72.87	84.81	71.06	77.65	63.68
	bDGlcp	105.29	75.54	77.19	81.28	77.51	63.00

There is only one chemically distinct structure:

*OC[C@H]1O[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](*)[C@H](O)[C@H]3O)[C@@H]2O)[C@H](O)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO[C@]4(C(=O)O)C[C@H](O)[C@@H](NC(C)=O)[C@H]([C@H](O)[C@H](O)CO)O4)[C@H](O)[C@H](O)[C@H]3NC(C)=O)[C@H](O)[C@H]2NC(C)=O)[C@H]1O

SVG MW SMILES 3D mol Ionize