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Taxonomic group: bacteria / Firmicutes (Phylum: Firmicutes)
Associated disease: infection due to Streptococcus pneumoniae [ICD11: XN3PW

]

The structure was elucidated in this paper
NCBI PubMed ID: 10795810
Publication DOI: 10.1016/S0008-6215(99)00331-6
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: cjones

nibsc.ac.uk
Institutions: Laboratory for Molecular Structure, National Institute for Biological Standards and Control, South Mimms, UK, Division of Bacteriology, National Institute for Biological Standards and Control, South Mimms, UK

Full proton, 13C and 31P NMR assignments for the capsular polysaccharide from Streptococcus pneumoniae Type 17F are reported, and a revised structure differing in the anomeric configuration of the sidechain β-Galp residue proposed. This polysaccharide is a component of the current 23-valent polysaccharide vaccine. The implications of this revised structure for published work are discussed.

structure, Streptococcus pneumoniae, capsular polysaccharide, NMR spectroscopy

Structure type: polymer chemical repeating unit
Location inside paper: p.196, table 1, p.199, CPS 4
Compound class: CPS
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_151528,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

Methods: NMR
Biological activity: vaccine component
Comments, role: revised structure

Related record ID(s): 931
NCBI Taxonomy refs (TaxIDs): 1313
Reference(s) to other database(s): GTC:G70730SZ, GlycomeDB:25293
Show glycosyltransferases

NMR conditions: in D2O at 323 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
0,2,4,3,3,4	bLRhap	101.26	70.97	78.56	71.92	72.93	17.78
0,2,4,3,3	bDGlcp	105.07	74.24	76.38	77.73	75.52	61.83
0,2,4,3	aDGalp	93.94	67.71	80.73	70.26	71.64	62.24
0,2,4,2	80%Ac	174.12	21.31
0,2,4,4	bDGalp	103.98	71.76	74.56	69.82	75.86	62.17
0,2,4	bLRhap	99.99	68.05	73.60	76.67	72.54	18.29
0,2	aLRhap	100.30	71.20	70.13	84.01	68.56	17.61
0	xDAra-ol	66.42	76.01	70.97	71.76	64.07
	P


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
0,2,4,3,3,4	bLRhap	4.908	4.275	4.049	3.512	3.450	1.341
0,2,4,3,3	bDGlcp	4.611	3.410	3.652	3.662	3.518	3.836-3.908
0,2,4,3	aDGalp	5.139	3.976	4.093	4.212	4.312	3.739-3.762
0,2,4,2	80%Ac	-	2.184
0,2,4,4	bDGalp	4.672	3.514	3.576	3.918	3.688	3.768-3.828
0,2,4	bLRhap	4.950	5.727	4.109	3.978	3.665	1.425
0,2	aLRhap	5.077	4.078	3.895	3.602	3.860	1.288
0	xDAra-ol	4.10-4.13	4.161	3.693	3.693	3.688-3.829
	P


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
0,2,4,3,3,4	bLRhap	101.26/4.908	70.97/4.275	78.56/4.049	71.92/3.512	72.93/3.450	17.78/1.341
0,2,4,3,3	bDGlcp	105.07/4.611	74.24/3.410	76.38/3.652	77.73/3.662	75.52/3.518	61.83/3.836-3.908
0,2,4,3	aDGalp	93.94/5.139	67.71/3.976	80.73/4.093	70.26/4.212	71.64/4.312	62.24/3.739-3.762
0,2,4,2	80%Ac		21.31/2.184
0,2,4,4	bDGalp	103.98/4.672	71.76/3.514	74.56/3.576	69.82/3.918	75.86/3.688	62.17/3.768-3.828
0,2,4	bLRhap	99.99/4.950	68.05/5.727	73.60/4.109	76.67/3.978	72.54/3.665	18.29/1.425
0,2	aLRhap	100.30/5.077	71.20/4.078	70.13/3.895	84.01/3.602	68.56/3.860	17.61/1.288
0	xDAra-ol	66.42/4.10-4.13	76.01/4.161	70.97/3.693	71.76/3.693	64.07/3.688-3.829
	P

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
0,2,4,3,3,4	bLRhap	4.908	4.275	4.049	3.512	3.450	1.341
0,2,4,3,3	bDGlcp	4.611	3.410	3.652	3.662	3.518	3.836 3.908
0,2,4,3	aDGalp	5.139	3.976	4.093	4.212	4.312	3.739 3.762
0,2,4,2	80%Ac		2.184
0,2,4,4	bDGalp	4.672	3.514	3.576	3.918	3.688	3.768 3.828
0,2,4	bLRhap	4.950	5.727	4.109	3.978	3.665	1.425
0,2	aLRhap	5.077	4.078	3.895	3.602	3.860	1.288
0	xDAra-ol	4.10 4.13	4.161	3.693	3.693	3.688 3.829
	P

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
0,2,4,3,3,4	bLRhap	101.26	70.97	78.56	71.92	72.93	17.78
0,2,4,3,3	bDGlcp	105.07	74.24	76.38	77.73	75.52	61.83
0,2,4,3	aDGalp	93.94	67.71	80.73	70.26	71.64	62.24
0,2,4,2	80%Ac	174.12	21.31
0,2,4,4	bDGalp	103.98	71.76	74.56	69.82	75.86	62.17
0,2,4	bLRhap	99.99	68.05	73.60	76.67	72.54	18.29
0,2	aLRhap	100.30	71.20	70.13	84.01	68.56	17.61
0	xDAra-ol	66.42	76.01	70.97	71.76	64.07
	P

There is only one chemically distinct structure:

*O[C@@H]1[C@@H](O)[C@H](C)O[C@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@H]3[C@@H](O)[C@@H](CO)O[C@H](O[C@@H]4[C@@H](O[C@@H]5O[C@H](CO)[C@H](O)[C@H](O)[C@H]5O)[C@H](C)O[C@H](O[C@H]5[C@H](C)O[C@@H](O[C@H](COP(*)(=O)O)[C@H](O)[C@H](O)CO)[C@H](O)[C@@H]5O)[C@@H]4OC(C)=O)[C@@H]3O)[C@H](O)[C@H]2O)[C@@H]1O

SVG MW SMILES 3D mol Ionize