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Taxonomic group: bacteria / Firmicutes (Phylum: Firmicutes)
Host organism: Sus scrofa
Associated disease: meningitis [ICD11: 1D01

]; septicemia [ICD11: MA15.Y

]; inflammatory arthropathies [ICD11: FA2Z

]; infection due to Streptococcus suis [ICD11: XN5SE

]

The structure was elucidated in this paper
NCBI PubMed ID: 30605786
Publication DOI: 10.1016/j.carres.2018.12.009
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: M. Segura <mariela.segura

umontreal.ca>
Institutions: Swine and Poultry Infectious Diseases Research Center, Faculty of Veterinary Medicine, University of Montreal, 3200 Sicotte St., St-Hyacinthe, Quebec, J2S 2M2, Canada, Canadian Glycomics Network (GlycoNet), University of Alberta, 11227 Saskatchewan Dr., Edmonton, Alberta, T6G 2G2, Canada, National Research Council, 100 Sussex Dr., Ottawa, Ontario, K1A 0R6, Canada, Division of Bacterial and Parasitic Disease, National Institute of Animal Health, National Agriculture and Food Research Organization, 3-1-5 Kannondai, Tsukuba, Ibaraki, 305-0856, Japan, The United Graduate School of Veterinary Sciences, Gifu University, 1-1 Yanagido, Gifu, Gifu, 501-1193, Japan

Streptococcus suis serotypes 7 and 8 are counted among the top six S. suis serotypes causing clinical disease in pigs. Yet, limited information is available on these serotypes. Since S. suis serotyping system is based upon capsular polysaccharide (CPS) antigenicity and the CPS is considered a major virulence factor for encapsulated pathogens, here we determined for the first time the chemical compositions and structures of serotypes 7 and 8 CPSs. Chemical and spectroscopic data gave the following repeating unit sequences: [3)L-Rha(α1-P-2)D-Gal(α1-4)D-GlcA(β1-3)D-FucNAc4N(α1-]n for serotype 7 and [2)L-Rha(α1-P-4)D-ManNAc(β1-4)D-Glc(α1-]n for serotype 8. As serotype 8 CPS is identical to Streptococcus pneumoniae type 19F CPS, dot-blot analyses showed a strong reaction of the 19F polysaccharide with reference anti-S. suis serotype 8 rabbit serum. A correlation between S. suis serotypes 7 and 8 sequences and genes of those serotypes' loci encoding putative glycosyltransferases and polymerases responsible for the biosynthesis of the repeating units was tentatively established. Knowledge of CPS structure and composition will contribute to better dissect the role of this bacterial component in the pathogenesis of the disease caused by S. suis serotypes 7 and 8.

capsular polysaccharide, carbohydrate structure, Serotype 8, Streptococcus suis, Serotype 7

Structure type: oligomer
Location inside paper: abstract, table 2, p.39, S. suis 8
Compound class: CPS
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158557,IEDB_225177,IEDB_885813,IEDB_885823,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, GLC-MS, gel filtration, NMR-2D, sugar analysis, 31P NMR, acid hydrolysis, Western blotting, bioinformatic analysis
Comments, role: native CPS

Related record ID(s): 737, 739, 740, 741, 742, 743, 744, 745, 746, 747, 748, 749, 750, 751, 752, 753, 754, 755, 756, 757, 1019
NCBI Taxonomy refs (TaxIDs): 1307
Reference(s) to other database(s): GTC:G16844DY
Show glycosyltransferases

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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
2,4,4,0,2,4,2	Ac	176.7	23.2
2,4,4,0,2,4	bDManpN	100.5	54.3	72.5	73.3	76.8	61.6
2,4,4,0,2	aDGlcp	98.9	72.2	72.4	79.8	71.5	60.9
2,4,4,0	aLRhap	95.0	78.0	70.2	72.8	71.3	17.9
2,4,4	P
2,4,4,0,2,4,4,0,2,4,2	Ac	176.7	23.2
2,4,4,0,2,4,4,0,2,4,4	P
2,4,4,0,2,4,4,0,2,4	bDManpN	100.5	54.3	72.5	72.6	76.8	61.6
2,4,4,0,2,4,4,0,2	aDGlcp
2,4,4,0,2,4,4,0	aLRhap
2,4,4,0,2,4,4	P
2,4,2	Ac	176.7	23.2
2,4	bDManpN
2	aDGlcp	102.1	73.0	72.6	79.8	71.5	60.9
	bLRhap	94.9	82.0	73.1	73.0	73.4	17.9


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2,4,4,0,2,4,2	Ac	-	2.09
2,4,4,0,2,4	bDManpN	4.92	4.58	4.00	4.08	3.56	3.86-3.94
2,4,4,0,2	aDGlcp	5.02	3.58	3.90	3.70	4.09	3.76-3.76
2,4,4,0	aLRhap	5.50	4.03	3.93	3.52	3.89	1.31
2,4,4	P
2,4,4,0,2,4,4,0,2,4,2	Ac	-	2.09
2,4,4,0,2,4,4,0,2,4,4	P
2,4,4,0,2,4,4,0,2,4	bDManpN	4.92	4.58	4.00	4.05	3.56	3.86-3.94
2,4,4,0,2,4,4,0,2	aDGlcp
2,4,4,0,2,4,4,0	aLRhap
2,4,4,0,2,4,4	P
2,4,2	Ac	-	2.09
2,4	bDManpN
2	aDGlcp	5.09	3.62	3.93	3.71	4.09	3.76-3.76
	bLRhap	4.94	4.00	3.66	3.37	3.43	1.30


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
2,4,4,0,2,4,2	Ac		23.2/2.09
2,4,4,0,2,4	bDManpN	100.5/4.92	54.3/4.58	72.5/4.00	73.3/4.08	76.8/3.56	61.6/3.86-3.94
2,4,4,0,2	aDGlcp	98.9/5.02	72.2/3.58	72.4/3.90	79.8/3.70	71.5/4.09	60.9/3.76-3.76
2,4,4,0	aLRhap	95.0/5.50	78.0/4.03	70.2/3.93	72.8/3.52	71.3/3.89	17.9/1.31
2,4,4	P
2,4,4,0,2,4,4,0,2,4,2	Ac		23.2/2.09
2,4,4,0,2,4,4,0,2,4,4	P
2,4,4,0,2,4,4,0,2,4	bDManpN	100.5/4.92	54.3/4.58	72.5/4.00	72.6/4.05	76.8/3.56	61.6/3.86-3.94
2,4,4,0,2,4,4,0,2	aDGlcp
2,4,4,0,2,4,4,0	aLRhap
2,4,4,0,2,4,4	P
2,4,2	Ac		23.2/2.09
2,4	bDManpN
2	aDGlcp	102.1/5.09	73.0/3.62	72.6/3.93	79.8/3.71	71.5/4.09	60.9/3.76-3.76
	bLRhap	94.9/4.94	82.0/4.00	73.1/3.66	73.0/3.37	73.4/3.43	17.9/1.30

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
2,4,4,0,2,4,2	Ac		2.09
2,4,4,0,2,4	bDManpN	4.92	4.58	4.00	4.08	3.56	3.86 3.94
2,4,4,0,2	aDGlcp	5.02	3.58	3.90	3.70	4.09	3.76 3.76
2,4,4,0	aLRhap	5.50	4.03	3.93	3.52	3.89	1.31
2,4,4	P
2,4,4,0,2,4,4,0,2,4,2	Ac		2.09
2,4,4,0,2,4,4,0,2,4,4	P
2,4,4,0,2,4,4,0,2,4	bDManpN	4.92	4.58	4.00	4.05	3.56	3.86 3.94
2,4,4,0,2,4,4,0,2	aDGlcp
2,4,4,0,2,4,4,0	aLRhap
2,4,4,0,2,4,4	P
2,4,2	Ac		2.09
2,4	bDManpN
2	aDGlcp	5.09	3.62	3.93	3.71	4.09	3.76 3.76
	bLRhap	4.94	4.00	3.66	3.37	3.43	1.30

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
2,4,4,0,2,4,2	Ac	176.7	23.2
2,4,4,0,2,4	bDManpN	100.5	54.3	72.5	73.3	76.8	61.6
2,4,4,0,2	aDGlcp	98.9	72.2	72.4	79.8	71.5	60.9
2,4,4,0	aLRhap	95.0	78.0	70.2	72.8	71.3	17.9
2,4,4	P
2,4,4,0,2,4,4,0,2,4,2	Ac	176.7	23.2
2,4,4,0,2,4,4,0,2,4,4	P
2,4,4,0,2,4,4,0,2,4	bDManpN	100.5	54.3	72.5	72.6	76.8	61.6
2,4,4,0,2,4,4,0,2	aDGlcp
2,4,4,0,2,4,4,0	aLRhap
2,4,4,0,2,4,4	P
2,4,2	Ac	176.7	23.2
2,4	bDManpN
2	aDGlcp	102.1	73.0	72.6	79.8	71.5	60.9
	bLRhap	94.9	82.0	73.1	73.0	73.4	17.9

There is only one chemically distinct structure:

CC(=O)N[C@@H]1[C@H](O[C@@H]2[C@@H](CO)O[C@H](O[C@H]3[C@H](OP(=O)(O)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](OP(=O)(O)O[C@@H]7[C@@H](CO)O[C@@H](O[C@@H]8[C@@H](CO)O[C@H](O[C@H]9[C@H](OP(=O)(O)O[C@@H]%10[C@@H](CO)O[C@@H](O[C@@H]%11[C@@H](CO)O[C@H](O[C@H]%12[C@H](OP(=O)(O)O[C@@H]%13[C@@H](CO)O[C@@H](O[C@@H]%14[C@@H](CO)O[C@H](O[C@H]%15[C@@H](O)O[C@@H](C)[C@H](O)[C@H]%15O)[C@H](O)[C@H]%14O)[C@@H](NC(C)=O)[C@H]%13O)O[C@@H](C)[C@H](O)[C@H]%12O)[C@H](O)[C@H]%11O)[C@@H](NC(C)=O)[C@H]%10O)O[C@@H](C)[C@H](O)[C@H]9O)[C@H](O)[C@H]8O)[C@@H](NC(C)=O)[C@H]7O)O[C@@H](C)[C@H](O)[C@H]6O)[C@H](O)[C@H]5O)[C@@H](NC(C)=O)[C@H]4O)O[C@@H](C)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)O[C@H](CO)[C@@H](OP(=O)(O)O)[C@@H]1O

SVG MW SMILES 3D mol Ionize

Warning = sub-repeat ending at xXP?: unknown unit count was assumed to be 3