Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: infection due to Streptococcus pneumoniae [ICD11:
XN3PW 
]
The structure was elucidated in this paperNCBI PubMed ID: 35483835Publication DOI: 10.1016/j.carbpol.2022.119414Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: C. Zong <chengli.zong
hainanu.edu.cn>
Institutions: School of Pharmaceutical Sciences, College of Marine Science, Hainan University, Haikou 570228, China, The University of Sydney, NSW 2006, Australia, School of Pharmacy, Fudan University, Shanghai 201203, China
Around 100 Streptococcus pneumonia (Spn) serotypes have been discovered, 90% of the severe diseases in children are caused by 13 serotypes. With the success of pneumococcal bacterial polysaccharide conjugate vaccines (PCVs), the burden of pneumococcal disease has been significantly reduced. Serotype 31 is a non-vaccine serotype and has increased in prevalence. By using Nuclear Magnetic Resonance (NMR) as the primary tool, we report the revised serotype 31 polysaccharide (s-31-ps) structure as [→3)-β-D-Galf-(5/6-OAc)-(1→3)-β-D-Galp-(1→3)-β-L-Rhap-(2-OAc)-(1→2)-α-L-Rhap-(1→4)-β-D-GlcpA-(1→]n. Furthermore, the reductive amination-conjugate of serotype 31 polysaccharide and cross reacting material (CRM197) protein was prepared in organic solvent (N,N-dimethylformamide, DMF) instead of water. The reaction is faster, and the DMF conjugate elicited comparable immune responses with the aqueous conjugate. S-31-ps conjugate vaccine has the potential of being included in the next-generation PCV vaccines.
Streptococcus pneumoniae polysaccharide, polysaccharide conjugate vaccine, serotype 31 polysaccharide, CRM197 conjugate, organic solvent
Structure type: polymer chemical repeating unit
Location inside paper: Fig. 3A, table 1, s-31-ps
Compound class: CPS
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_136095,IEDB_136105,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, periodate oxidation, GC-MS, ELISA, acid hydrolysis, de-O-acetylation, HPLC, GPC, computer analysis with CASPER, conjugation, TEM, NOESY, vaccination, vaccine formulation, HPSEC-UV, PMP derivatization, CRM197 formulation
Comments, role: O-deacetylated CPS from S. pneumoniae serotype 31 (revised structure from Batavyal & Roy, 1983, DOI:10.1016/0008-6215(83)84069-5, see ID: 113903); NMR temperature was not specified.
Related record ID(s): 8833
NCBI Taxonomy refs (TaxIDs): 1313
Show glycosyltransferases
NMR conditions: in D2O
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,2,3,3 bDGalf 110.3 80.4 85.7 82.2 70.6 63.9
4,2,3 bDGalp 104.7 70.8 81.1 69.0 75.6 61.3
4,2 bLRhap 97.0 73.10 81.1 72.1 72.1 17.5
4 aLRhap 98.3 77.5 72.6 73.4 70.8 17.2
bDGlcpA 102.8 73.7 74.7 79.8 76.7 175.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,2,3,3 bDGalf 5.22 4.36 4.06 4.41 5.45 4.33
4,2,3 bDGalp 4.64 3.61 3.72 4.04 3.69 3.65-3.73
4,2 bLRhap 4.84 5.54 4.05 3.58 3.58 1.35
4 aLRhap 4.80 4.06 3.76 3.23 3.67 1.21
bDGlcpA 4.51 3.36 3.56 3.58 3.73 -
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,2,3,3 bDGalf 110.3/5.22 80.4/4.36 85.7/4.06 82.2/4.41 70.6/5.45 63.9/4.33
4,2,3 bDGalp 104.7/4.64 70.8/3.61 81.1/3.72 69.0/4.04 75.6/3.69 61.3/3.65-3.73
4,2 bLRhap 97.0/4.84 73.10/5.54 81.1/4.05 72.1/3.58 72.1/3.58 17.5/1.35
4 aLRhap 98.3/4.80 77.5/4.06 72.6/3.76 73.4/3.23 70.8/3.67 17.2/1.21
bDGlcpA 102.8/4.51 73.7/3.36 74.7/3.56 79.8/3.58 76.7/3.73
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,2,3,3 | bDGalf | 5.22 | 4.36 | 4.06 | 4.41 | 5.45 | 4.33 |
| 4,2,3 | bDGalp | 4.64 | 3.61 | 3.72 | 4.04 | 3.69 | 3.65
3.73 |
| 4,2 | bLRhap | 4.84 | 5.54 | 4.05 | 3.58 | 3.58 | 1.35 |
| 4 | aLRhap | 4.80 | 4.06 | 3.76 | 3.23 | 3.67 | 1.21 |
| | bDGlcpA | 4.51 | 3.36 | 3.56 | 3.58 | 3.73 |
|
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,2,3,3 | bDGalf | 110.3 | 80.4 | 85.7 | 82.2 | 70.6 | 63.9 |
| 4,2,3 | bDGalp | 104.7 | 70.8 | 81.1 | 69.0 | 75.6 | 61.3 |
| 4,2 | bLRhap | 97.0 | 73.10 | 81.1 | 72.1 | 72.1 | 17.5 |
| 4 | aLRhap | 98.3 | 77.5 | 72.6 | 73.4 | 70.8 | 17.2 |
| | bDGlcpA | 102.8 | 73.7 | 74.7 | 79.8 | 76.7 | 175.6 |
|
There is only one chemically distinct structure:
Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Associated disease: infection due to Streptococcus pneumoniae [ICD11:
XN3PW ]
The structure was elucidated in this paperNCBI PubMed ID: 35483835Publication DOI: 10.1016/j.carbpol.2022.119414Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: C. Zong <chengli.zong
hainanu.edu.cn>
Institutions: School of Pharmaceutical Sciences, College of Marine Science, Hainan University, Haikou 570228, China, The University of Sydney, NSW 2006, Australia, School of Pharmacy, Fudan University, Shanghai 201203, China
Around 100 Streptococcus pneumonia (Spn) serotypes have been discovered, 90% of the severe diseases in children are caused by 13 serotypes. With the success of pneumococcal bacterial polysaccharide conjugate vaccines (PCVs), the burden of pneumococcal disease has been significantly reduced. Serotype 31 is a non-vaccine serotype and has increased in prevalence. By using Nuclear Magnetic Resonance (NMR) as the primary tool, we report the revised serotype 31 polysaccharide (s-31-ps) structure as [→3)-β-D-Galf-(5/6-OAc)-(1→3)-β-D-Galp-(1→3)-β-L-Rhap-(2-OAc)-(1→2)-α-L-Rhap-(1→4)-β-D-GlcpA-(1→]n. Furthermore, the reductive amination-conjugate of serotype 31 polysaccharide and cross reacting material (CRM197) protein was prepared in organic solvent (N,N-dimethylformamide, DMF) instead of water. The reaction is faster, and the DMF conjugate elicited comparable immune responses with the aqueous conjugate. S-31-ps conjugate vaccine has the potential of being included in the next-generation PCV vaccines.
Streptococcus pneumoniae polysaccharide, polysaccharide conjugate vaccine, serotype 31 polysaccharide, CRM197 conjugate, organic solvent
Structure type: polymer chemical repeating unit
Location inside paper: abstract, p. 119414-6, s-31-ps
Trivial name: s-31-ps
Compound class: CPS
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_136095,IEDB_136105,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88
Methods: 13C NMR, 1H NMR, periodate oxidation, GC-MS, ELISA, acid hydrolysis, de-O-acetylation, HPLC, GPC, computer analysis with CASPER, conjugation, TEM, NOESY, vaccination, vaccine formulation, HPSEC-UV, PMP derivatization, CRM197 formulation
Comments, role: revised structure of the CPS of S. pneumoniae serotype 31 (revised structure from Batavyal & Roy, 1983, DOI:10.1016/0008-6215(83)84069-5, see ID: 113903)
Related record ID(s): 8554
NCBI Taxonomy refs (TaxIDs): 1313
Show glycosyltransferases
There is only one chemically distinct structure:
report error
Found 2 records.
Displayed records from 1 to 2
