Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Host organism: Homo sapiens
Associated disease: sinusitis [ICD11:
SC91 
];
acute otitis media [ICD11:
AB00 , Life stage: adult];
meningitis [ICD11:
1D01 ];
septicemia [ICD11:
MA15.Y ];
pneumonia [ICD11:
CA40 ];
infection due to Streptococcus pneumoniae [ICD11:
XN3PW ]
The structure was elucidated in this paperNCBI PubMed ID: 23981856Publication DOI: 10.1016/j.carres.2013.08.001Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: fiona.lin
pfizer.com
Institutions: Pfizer Vaccine Research, 401 N. Middletown Road, Pearl River, NY 10965, USA
In order to better understand cross-reactions of serogroup 33 polysaccharides and the typing sera, the structure of pneumococcal capsular polysaccharide serotype 33A was elucidated. Serotype 33A has been shown to have an identical polysaccharide backbone as that of serotype 33F, with two additional sites of O-acetylation at C5, and C6 of the 3-β-Galf residue in serotype 33A. This finding is consistent with the presence of an additional functional acetyltransferase gene (wcjE) in the cps biosynthetic locus of serotype 33A compared to 33F. The identical polysaccharide backbone with at least one common O-acetylation site (C2 of 5-β-Galf) shared by serotype 33A and 33F polysaccharides is proposed to be the epitope recognized by typing serum 33b. In addition, a 5,6-di-O-acetylated →3)-β-D-Galf5,6Ac-(1→3)-β-D-Glcp-(1→ disaccharide unit, a common structural motif present in serotypes 33A, 20, and 35A polysaccharides, is proposed to be the antigenic determinant recognized by typing serum 20b.
Streptococcus pneumoniae, antigenic determinant, capsular polysaccharide structure, acetyltransferase, Serotype 33A
Structure type: polymer chemical repeating unit
Location inside paper: p.103, fig.1, p.106, fig.5, fig.6
Compound class: CPS
Contained glycoepitopes: IEDB_131186,IEDB_135818,IEDB_136044,IEDB_136095,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_190606,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, acid hydrolysis, MS/MS, de-O-acetylation, NMR-1D, HPAEC-PAD, CE-MS
Related record ID(s): 29635, 29636, 29637
NCBI Taxonomy refs (TaxIDs): 1313Reference(s) to other database(s): GTC:G56629SU
Show glycosyltransferases
NMR conditions: in D2O at 300 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
5,3,3,3 bDGalp 104.9 71.1 81.8 69.7 75.8 62.3
5,3,3,2 aDGalp 95.5 69.3 70.5 70.5 72.0 62.3
5,3,3 aDGalp 98.2 69.7 77.5 70.5 72.1 62.2
5,3,5 Ac
5,3,6 Ac
5,3 bDGalf 109.5 80.5 86.9 81.0 70.3 64.8
5 bDGlcp 103.0 74.8 82.9 69.3 76.9 62.1
2 Ac
bDGalf 108.1 85.1 76.2 83.7 78.4 62.2
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
5,3,3,3 bDGalp 4.68 3.68 3.72 4.07 3.71 3.75
5,3,3,2 aDGalp 5.16 3.85 3.94 3.95 4.34 3.74-3.77
5,3,3 aDGalp 5.38 4.18 4.18 4.28 4.12 3.76
5,3,5 Ac
5,3,6 Ac
5,3 bDGalf 5.36 4.40 3.82 4.49 5.57 4.33-4.37
5 bDGlcp 4.64 3.44 3.67 3.42 3.49 3.72-3.94
2 Ac
bDGalf 5.37 5.04 4.50 4.27 4.12 3.79-3.83
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
5,3,3,3 bDGalp 104.9/4.68 71.1/3.68 81.8/3.72 69.7/4.07 75.8/3.71 62.3/3.75
5,3,3,2 aDGalp 95.5/5.16 69.3/3.85 70.5/3.94 70.5/3.95 72.0/4.34 62.3/3.74-3.77
5,3,3 aDGalp 98.2/5.38 69.7/4.18 77.5/4.18 70.5/4.28 72.1/4.12 62.2/3.76
5,3,5 Ac
5,3,6 Ac
5,3 bDGalf 109.5/5.36 80.5/4.40 86.9/3.82 81.0/4.49 70.3/5.57 64.8/4.33-4.37
5 bDGlcp 103.0/4.64 74.8/3.44 82.9/3.67 69.3/3.42 76.9/3.49 62.1/3.72-3.94
2 Ac
bDGalf 108.1/5.37 85.1/5.04 76.2/4.50 83.7/4.27 78.4/4.12 62.2/3.79-3.83
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 5,3,3,3 | bDGalp | 4.68 | 3.68 | 3.72 | 4.07 | 3.71 | 3.75 |
| 5,3,3,2 | aDGalp | 5.16 | 3.85 | 3.94 | 3.95 | 4.34 | 3.74
3.77 |
| 5,3,3 | aDGalp | 5.38 | 4.18 | 4.18 | 4.28 | 4.12 | 3.76 |
| 5,3,5 | Ac | |
| 5,3,6 | Ac | |
| 5,3 | bDGalf | 5.36 | 4.40 | 3.82 | 4.49 | 5.57 | 4.33
4.37 |
| 5 | bDGlcp | 4.64 | 3.44 | 3.67 | 3.42 | 3.49 | 3.72
3.94 |
| 2 | Ac | |
| | bDGalf | 5.37 | 5.04 | 4.50 | 4.27 | 4.12 | 3.79
3.83 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 5,3,3,3 | bDGalp | 104.9 | 71.1 | 81.8 | 69.7 | 75.8 | 62.3 |
| 5,3,3,2 | aDGalp | 95.5 | 69.3 | 70.5 | 70.5 | 72.0 | 62.3 |
| 5,3,3 | aDGalp | 98.2 | 69.7 | 77.5 | 70.5 | 72.1 | 62.2 |
| 5,3,5 | Ac | |
| 5,3,6 | Ac | |
| 5,3 | bDGalf | 109.5 | 80.5 | 86.9 | 81.0 | 70.3 | 64.8 |
| 5 | bDGlcp | 103.0 | 74.8 | 82.9 | 69.3 | 76.9 | 62.1 |
| 2 | Ac | |
| | bDGalf | 108.1 | 85.1 | 76.2 | 83.7 | 78.4 | 62.2 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
