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Van Calsteren MR, Gagnon F, Calzas C, Goyette-Desjardins G, Okura M, Takamatsu D, Gottschalk M, Segura M
Structure determination of Streptococcus suis serotype 14 capsular polysaccharide
Biochemistry and Cell Biology 91(2) (2013)
49-58
|
a-Neup5Ac-(2-6)-b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-+
|
-6)-b-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1- |
Show graphically |
Streptococcus suis 14 (DAN 13730)
(Ancestor NCBI TaxID 1307,
species name lookup)
Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Host organism: Homo sapiens
Associated disease: meningitis [ICD11:
1D01 
];
streptococcal toxic shock [ICD11:
1B52.0 , ICD11:
XN3NM ];
infection due to Streptococcus suis [ICD11:
XN5SE ]
The structure was elucidated in this paperNCBI PubMed ID: 23527632Publication DOI: 10.1139/bcb-2012-0036Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
Correspondence: marie-rose.vancalsteren
agr.gc.ca
Institutions: Groupe de recherche sur les maladies infectieuses du porc (GREMIP) and Centre de recherche en infectiologie porcine (CRIP), Faculté de médecine vétérinaire, Université de Montréal, Saint-Hyacinthe, QC J2S 2M2, Canada, Food Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC J2S 8E3, Canada, Bacterial and Parasitic Disease Research Division, National Institute of Animal Health, National Agriculture and Food Research Organization, Tsukuba, Japan
The capsular polysaccharide (CPS) of Streptococcus suis serotype 14 was purified, chemically modified, and characterized. Sugar and absolute configuration analyses gave the following CPS composition: D-Gal, 3; D-Glc, 1; D-GlcNAc, 1; D-Neu5Ac, 1. The Sambucus nigra lectin, which recognizes the Neu5Ac(α2-6)Gal/GalNAc sequence, showed binding to the native CPS. Sialic acid was found to be terminal, and the CPS was quantitatively desialylated by mild acid hydrolysis. It was also submitted to periodate oxidation followed by borohydride reduction and Smith degradation. Sugar and methylation analyses, (1)H and (13)C nuclear magnetic resonance, and mass spectrometry of the native CPS or of its specifically modified products allowed to determine the repeating unit sequence: [6)[Neu5Ac(α2-6)Gal(β1-4)GlcNAc(β1-3)]Gal(β1-3)Gal(β1-4)Glc(β1 -](n). S. suis serotype 14 CPS has an identical sialic acid-containing side chain as serotype 2 CPS, but differs by the absence of rhamnose in its composition. The same side chain is also present in group B Streptococcus type Ia CPS, except that in the latter sialic acid is 2,3- rather than 2,6-linked to the following galactose. A correlation between the S. suis CPS sequence and genes of the serotype 14 cps locus encoding putative glycosyltransferases and polymerase responsible for the biosynthesis of the repeating unit is proposed.
chemical modification, nuclear magnetic resonance (NMR), mass spectrometry (MS), repeating unit sequence, Streptococcus suis serotype 14
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.55, p.57, fig.5
Compound class: CPS
Contained glycoepitopes: IEDB_130646,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_146100,IEDB_146664,IEDB_149174,IEDB_151531,IEDB_158551,IEDB_190606,IEDB_548866,IEDB_548869,IEDB_983931,SB_126,SB_132,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_6,SB_7,SB_84,SB_88
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, ESI-MS, mild acid hydrolysis, Smith degradation, NMR-1D, methanolysis
Biological activity: lectin binding assays
Related record ID(s): 29784, 29785
NCBI Taxonomy refs (TaxIDs): 1307Reference(s) to other database(s): GTC:G57867VP
Show glycosyltransferases
NMR conditions: in D2O; pH 8 at 350 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9
4,3,3,4,6,5 Ac 177.64 24.78
4,3,3,4,6 aXNeup 175.93 103.07 42.83 70.92 54.74 75.30 71.35 74.48 65.59
4,3,3,4 bDGalp 105.96 73.59 75.31 71.22 76.42 66.00
4,3,3,2 Ac 177.45 25.07
4,3,3 bDGlcpN 105.08 57.96 74.91 83.02 77.19 63.20
4,3 bDGalp 106.77 72.91 84.48 71.02 75.91 71.52
4 bDGalp 105.32 72.87 84.78 71.06 77.64 63.68
bDGlcp 105.29 75.56 77.19 81.36 77.51 63.05
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 3.78 3.71 3.55 3.87 3.65-3.86
4,3,3,4 bDGalp 4.45 3.54 3.66 3.93 3.80 3.61-3.96
4,3,3,2 Ac - 2.05
4,3,3 bDGlcpN 4.77 3.78 3.79 3.66 3.60 3.83-3.95
4,3 bDGalp 4.62 3.67 3.74 4.15 3.86 3.87-4.03
4 bDGalp 4.50 3.71 3.81 4.18 3.73 3.77-3.79
bDGlcp 4.50 3.33 3.64 3.64 3.58 3.81-3.98
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 24.78/2.03
4,3,3,4,6 aXNeup 42.83/1.68-2.68 70.92/3.68 54.74/3.78 75.30/3.71 71.35/3.55 74.48/3.87 65.59/3.65-3.86
4,3,3,4 bDGalp 105.96/4.45 73.59/3.54 75.31/3.66 71.22/3.93 76.42/3.80 66.00/3.61-3.96
4,3,3,2 Ac 25.07/2.05
4,3,3 bDGlcpN 105.08/4.77 57.96/3.78 74.91/3.79 83.02/3.66 77.19/3.60 63.20/3.83-3.95
4,3 bDGalp 106.77/4.62 72.91/3.67 84.48/3.74 71.02/4.15 75.91/3.86 71.52/3.87-4.03
4 bDGalp 105.32/4.50 72.87/3.71 84.78/3.81 71.06/4.18 77.64/3.73 63.68/3.77-3.79
bDGlcp 105.29/4.50 75.56/3.33 77.19/3.64 81.36/3.64 77.51/3.58 63.05/3.81-3.98
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 | 3.78 | 3.71 | 3.55 | 3.87 | 3.65
3.86 |
| 4,3,3,4 | bDGalp | 4.45 | 3.54 | 3.66 | 3.93 | 3.80 | 3.61
3.96 | |
| 4,3,3,2 | Ac |
| 2.05 | |
| 4,3,3 | bDGlcpN | 4.77 | 3.78 | 3.79 | 3.66 | 3.60 | 3.83
3.95 | |
| 4,3 | bDGalp | 4.62 | 3.67 | 3.74 | 4.15 | 3.86 | 3.87
4.03 | |
| 4 | bDGalp | 4.50 | 3.71 | 3.81 | 4.18 | 3.73 | 3.77
3.79 | |
| | bDGlcp | 4.50 | 3.33 | 3.64 | 3.64 | 3.58 | 3.81
3.98 | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 |
|---|
| 4,3,3,4,6,5 | Ac | 177.64 | 24.78 | |
| 4,3,3,4,6 | aXNeup | 175.93 | 103.07 | 42.83 | 70.92 | 54.74 | 75.30 | 71.35 | 74.48 | 65.59 |
| 4,3,3,4 | bDGalp | 105.96 | 73.59 | 75.31 | 71.22 | 76.42 | 66.00 | |
| 4,3,3,2 | Ac | 177.45 | 25.07 | |
| 4,3,3 | bDGlcpN | 105.08 | 57.96 | 74.91 | 83.02 | 77.19 | 63.20 | |
| 4,3 | bDGalp | 106.77 | 72.91 | 84.48 | 71.02 | 75.91 | 71.52 | |
| 4 | bDGalp | 105.32 | 72.87 | 84.78 | 71.06 | 77.64 | 63.68 | |
| | bDGlcp | 105.29 | 75.56 | 77.19 | 81.36 | 77.51 | 63.05 | |
|
There is only one chemically distinct structure:
Expand this record
Collapse this record
Van Calsteren MR, Gagnon F, Calzas C, Goyette-Desjardins G, Okura M, Takamatsu D, Gottschalk M, Segura M
Structure determination of Streptococcus suis serotype 14 capsular polysaccharide
Biochemistry and Cell Biology 91(2) (2013)
49-58
|
b-D-Galp-(1-4)-b-D-GlcpNAc-(1-3)-+
|
-6)-b-D-Galp-(1-3)-b-D-Galp-(1-4)-b-D-Glcp-(1- |
Show graphically |
Streptococcus suis 14 (DAN 13730)
(Ancestor NCBI TaxID 1307,
species name lookup)
Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Host organism: Homo sapiens
Associated disease: meningitis [ICD11:
1D01 ];
streptococcal toxic shock [ICD11:
1B52.0 , ICD11:
XN3NM ];
infection due to Streptococcus suis [ICD11:
XN5SE ]
The structure was elucidated in this paperNCBI PubMed ID: 23527632Publication DOI: 10.1139/bcb-2012-0036Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
Correspondence: marie-rose.vancalsteren
agr.gc.ca
Institutions: Groupe de recherche sur les maladies infectieuses du porc (GREMIP) and Centre de recherche en infectiologie porcine (CRIP), Faculté de médecine vétérinaire, Université de Montréal, Saint-Hyacinthe, QC J2S 2M2, Canada, Food Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC J2S 8E3, Canada, Bacterial and Parasitic Disease Research Division, National Institute of Animal Health, National Agriculture and Food Research Organization, Tsukuba, Japan
The capsular polysaccharide (CPS) of Streptococcus suis serotype 14 was purified, chemically modified, and characterized. Sugar and absolute configuration analyses gave the following CPS composition: D-Gal, 3; D-Glc, 1; D-GlcNAc, 1; D-Neu5Ac, 1. The Sambucus nigra lectin, which recognizes the Neu5Ac(α2-6)Gal/GalNAc sequence, showed binding to the native CPS. Sialic acid was found to be terminal, and the CPS was quantitatively desialylated by mild acid hydrolysis. It was also submitted to periodate oxidation followed by borohydride reduction and Smith degradation. Sugar and methylation analyses, (1)H and (13)C nuclear magnetic resonance, and mass spectrometry of the native CPS or of its specifically modified products allowed to determine the repeating unit sequence: [6)[Neu5Ac(α2-6)Gal(β1-4)GlcNAc(β1-3)]Gal(β1-3)Gal(β1-4)Glc(β1 -](n). S. suis serotype 14 CPS has an identical sialic acid-containing side chain as serotype 2 CPS, but differs by the absence of rhamnose in its composition. The same side chain is also present in group B Streptococcus type Ia CPS, except that in the latter sialic acid is 2,3- rather than 2,6-linked to the following galactose. A correlation between the S. suis CPS sequence and genes of the serotype 14 cps locus encoding putative glycosyltransferases and polymerase responsible for the biosynthesis of the repeating unit is proposed.
chemical modification, nuclear magnetic resonance (NMR), mass spectrometry (MS), repeating unit sequence, Streptococcus suis serotype 14
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.55, p.57, fig.5
Compound class: CPS
Contained glycoepitopes: IEDB_130646,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_140108,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_548869,IEDB_983931,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_6,SB_7,SB_88
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, ESI-MS, mild acid hydrolysis, Smith degradation, NMR-1D, methanolysis
Biological activity: lectin binding assays
Comments, role: the desialylated polysaccharide
Related record ID(s): 29371, 29785
NCBI Taxonomy refs (TaxIDs): 1307Reference(s) to other database(s): GTC:G57688EQ
Show glycosyltransferases
NMR conditions: in D2O at 333 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,3,3,4 bDGalp 105.63 73.73 75.39 71.32 78.02 63.65
4,3,3,2 Ac 177.45 24.96
4,3,3 bDGlcpN 105.18 58.08 74.93 81.48 77.36 62.95
4,3 bDGalp 106.76 72.89 84.48 71.06 75.99 71.62
4 bDGalp 105.31 72.87 84.70 71.06 77.66 63.67
bDGlcp 105.31 75.56 77.18 81.36 77.49 63.06
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,3,3,4 bDGalp 4.48 3.55 3.66 3.93 3.72 3.77
4,3,3,2 Ac - 2.03
4,3,3 bDGlcpN 4.75 3.77 3.76 3.71 3.59 3.83-3.96
4,3 bDGalp 4.62 3.67 3.73 4.14 3.86 3.89-4.02
4 bDGalp 4.50 3.71 3.81 4.18 3.73 3.77-3.79
bDGlcp 4.50 3.33 3.64 3.64 3.59 3.80-3.98
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,3,3,4 bDGalp 105.63/4.48 73.73/3.55 75.39/3.66 71.32/3.93 78.02/3.72 63.65/3.77
4,3,3,2 Ac 24.96/2.03
4,3,3 bDGlcpN 105.18/4.75 58.08/3.77 74.93/3.76 81.48/3.71 77.36/3.59 62.95/3.83-3.96
4,3 bDGalp 106.76/4.62 72.89/3.67 84.48/3.73 71.06/4.14 75.99/3.86 71.62/3.89-4.02
4 bDGalp 105.31/4.50 72.87/3.71 84.70/3.81 71.06/4.18 77.66/3.73 63.67/3.77-3.79
bDGlcp 105.31/4.50 75.56/3.33 77.18/3.64 81.36/3.64 77.49/3.59 63.06/3.80-3.98
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,3,3,4 | bDGalp | 4.48 | 3.55 | 3.66 | 3.93 | 3.72 | 3.77 |
| 4,3,3,2 | Ac |
| 2.03 | |
| 4,3,3 | bDGlcpN | 4.75 | 3.77 | 3.76 | 3.71 | 3.59 | 3.83
3.96 |
| 4,3 | bDGalp | 4.62 | 3.67 | 3.73 | 4.14 | 3.86 | 3.89
4.02 |
| 4 | bDGalp | 4.50 | 3.71 | 3.81 | 4.18 | 3.73 | 3.77
3.79 |
| | bDGlcp | 4.50 | 3.33 | 3.64 | 3.64 | 3.59 | 3.80
3.98 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,3,3,4 | bDGalp | 105.63 | 73.73 | 75.39 | 71.32 | 78.02 | 63.65 |
| 4,3,3,2 | Ac | 177.45 | 24.96 | |
| 4,3,3 | bDGlcpN | 105.18 | 58.08 | 74.93 | 81.48 | 77.36 | 62.95 |
| 4,3 | bDGalp | 106.76 | 72.89 | 84.48 | 71.06 | 75.99 | 71.62 |
| 4 | bDGalp | 105.31 | 72.87 | 84.70 | 71.06 | 77.66 | 63.67 |
| | bDGlcp | 105.31 | 75.56 | 77.18 | 81.36 | 77.49 | 63.06 |
|
There is only one chemically distinct structure:
Expand this record
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Van Calsteren MR, Gagnon F, Calzas C, Goyette-Desjardins G, Okura M, Takamatsu D, Gottschalk M, Segura M
Structure determination of Streptococcus suis serotype 14 capsular polysaccharide
Biochemistry and Cell Biology 91(2) (2013)
49-58
Streptococcus suis 14 (DAN 13730)
(Ancestor NCBI TaxID 1307,
species name lookup)
Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Host organism: Homo sapiens
Associated disease: meningitis [ICD11:
1D01 ];
streptococcal toxic shock [ICD11:
1B52.0 , ICD11:
XN3NM ];
infection due to Streptococcus suis [ICD11:
XN5SE ]
The structure was elucidated in this paperNCBI PubMed ID: 23527632Publication DOI: 10.1139/bcb-2012-0036Journal NLM ID: 8606068Publisher: Ottawa: National Research Council of Canada
Correspondence: marie-rose.vancalsteren
agr.gc.ca
Institutions: Groupe de recherche sur les maladies infectieuses du porc (GREMIP) and Centre de recherche en infectiologie porcine (CRIP), Faculté de médecine vétérinaire, Université de Montréal, Saint-Hyacinthe, QC J2S 2M2, Canada, Food Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC J2S 8E3, Canada, Bacterial and Parasitic Disease Research Division, National Institute of Animal Health, National Agriculture and Food Research Organization, Tsukuba, Japan
The capsular polysaccharide (CPS) of Streptococcus suis serotype 14 was purified, chemically modified, and characterized. Sugar and absolute configuration analyses gave the following CPS composition: D-Gal, 3; D-Glc, 1; D-GlcNAc, 1; D-Neu5Ac, 1. The Sambucus nigra lectin, which recognizes the Neu5Ac(α2-6)Gal/GalNAc sequence, showed binding to the native CPS. Sialic acid was found to be terminal, and the CPS was quantitatively desialylated by mild acid hydrolysis. It was also submitted to periodate oxidation followed by borohydride reduction and Smith degradation. Sugar and methylation analyses, (1)H and (13)C nuclear magnetic resonance, and mass spectrometry of the native CPS or of its specifically modified products allowed to determine the repeating unit sequence: [6)[Neu5Ac(α2-6)Gal(β1-4)GlcNAc(β1-3)]Gal(β1-3)Gal(β1-4)Glc(β1 -](n). S. suis serotype 14 CPS has an identical sialic acid-containing side chain as serotype 2 CPS, but differs by the absence of rhamnose in its composition. The same side chain is also present in group B Streptococcus type Ia CPS, except that in the latter sialic acid is 2,3- rather than 2,6-linked to the following galactose. A correlation between the S. suis CPS sequence and genes of the serotype 14 cps locus encoding putative glycosyltransferases and polymerase responsible for the biosynthesis of the repeating unit is proposed.
chemical modification, nuclear magnetic resonance (NMR), mass spectrometry (MS), repeating unit sequence, Streptococcus suis serotype 14
Structure type: oligomer
Location inside paper: p.56
Compound class: CPS
Contained glycoepitopes: IEDB_114707,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_141794,IEDB_141807,IEDB_151531,IEDB_190606,SB_165,SB_166,SB_173,SB_187,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, ESI-MS, mild acid hydrolysis, Smith degradation, NMR-1D, methanolysis
Biological activity: lectin binding assays
Comments, role: Smith degraded polysaccharide
Related record ID(s): 29371, 29784
NCBI Taxonomy refs (TaxIDs): 1307Reference(s) to other database(s): GTC:G08396WU
Show glycosyltransferases
There is only one chemically distinct structure:
Expand this record
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Total list of record IDs on all result pages of the current query:
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