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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
Publication DOI: 10.1139/v89-158
Journal NLM ID: 0372705
Publisher: National Research Council of Canada Canada
Institutions: Division of Biological Sciences, National Research Council, Ottawa, Ont., Canada KIA OR6

The structure of the specific capsular polysaccharide produced by Streptococcus pneumoniae type 22F (American type 22) was investigated by high-field 1H and 13C nuclear magnetic resonance spectroscopy, composition, methylation analysis, and periodate oxidation studies. The polysaccharide was found to be a high molecular weight acidic polymer composed of D-glucose, D-galactose, D-glucuronic acid, and L-rhamnose residues to form a regular repeating hexasaccharide unit having the structure [formula: see text] in which the β-L-rhamnopyranosyl residues were substituted by O-acetyl groups in 80% of the repeating units. The 1H and 13C nmr resonances of the O-deacetylated type 22F polysaccharide were completely assigned by application of two-dimensional homo- and heteronuclear chemical shift correlation techniques. Keywords: Streptococcuspneumoniae polysaccharide, NMR analysis.

NMR analysis, Streptococcus pneumoniae polysaccharide

Structure type: polymer chemical repeating unit
Location inside paper: p. 1044, structure 12
Compound class: CPS
Contained glycoepitopes: IEDB_115136,IEDB_136105,IEDB_137472,IEDB_140630,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_190606,IEDB_225177,IEDB_423153,IEDB_885823,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, methylation, GLC-MS, gel filtration, NMR-2D, sugar analysis, GLC, Smith degradation, de-O-acetylation, ion-exchange chromatography, optical rotation measurement
Comments, role: Streptococcus pneumoniae type 22F (American type 22); O-deacetylated OPS

Related record ID(s): 626, 627, 628, 112297
NCBI Taxonomy refs (TaxIDs): 1313
Reference(s) to other database(s): GTC:G42323NZ, GlycomeDB:4640
Show glycosyltransferases

NMR conditions: in D2O; pH 7 at 310 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
2,3,4,4	bDGlcpA	102.84	74.69	75.29	80.52	77.29	176.20
2,3,4,3	aDGlcp	94.23	72.24	74.28	70.63	72.61	61.27
2,3,4	bLRhap	101.33	66.78	76.66	76.79	72.08	18.11
2,3	aDGlcp	99.62	72.24	73.63	77.40	71.55	61.37
2	aDGalf	103.19	75.55	80.87	80.87	71.55	63.78
	aLRhap	99.98	80.40	70.34	73.17	70.02	17.19


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2,3,4,4	bDGlcpA	4.751	3.376	3.616	3.654	3.794	-
2,3,4,3	aDGlcp	5.257	3.636	3.845	3.479	4.045	3.807-3.875
2,3,4	bLRhap	4.930	4.407	3.976	3.878	3.550	1.398
2,3	aDGlcp	5.028	3.608	3.897	3.721	3.975	3.890-3.940
2	aDGalf	5.051	4.325	4.374	4.133	3.800	3.690-3.690
	aLRhap	4.818	3.958	3.816	3.437	4.051	1.294


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
2,3,4,4	bDGlcpA	102.84/4.751	74.69/3.376	75.29/3.616	80.52/3.654	77.29/3.794	
2,3,4,3	aDGlcp	94.23/5.257	72.24/3.636	74.28/3.845	70.63/3.479	72.61/4.045	61.27/3.807-3.875
2,3,4	bLRhap	101.33/4.930	66.78/4.407	76.66/3.976	76.79/3.878	72.08/3.550	18.11/1.398
2,3	aDGlcp	99.62/5.028	72.24/3.608	73.63/3.897	77.40/3.721	71.55/3.975	61.37/3.890-3.940
2	aDGalf	103.19/5.051	75.55/4.325	80.87/4.374	80.87/4.133	71.55/3.800	63.78/3.690-3.690
	aLRhap	99.98/4.818	80.40/3.958	70.34/3.816	73.17/3.437	70.02/4.051	17.19/1.294

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
2,3,4,4	bDGlcpA	4.751	3.376	3.616	3.654	3.794
2,3,4,3	aDGlcp	5.257	3.636	3.845	3.479	4.045	3.807 3.875
2,3,4	bLRhap	4.930	4.407	3.976	3.878	3.550	1.398
2,3	aDGlcp	5.028	3.608	3.897	3.721	3.975	3.890 3.940
2	aDGalf	5.051	4.325	4.374	4.133	3.800	3.690 3.690
	aLRhap	4.818	3.958	3.816	3.437	4.051	1.294

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
2,3,4,4	bDGlcpA	102.84	74.69	75.29	80.52	77.29	176.20
2,3,4,3	aDGlcp	94.23	72.24	74.28	70.63	72.61	61.27
2,3,4	bLRhap	101.33	66.78	76.66	76.79	72.08	18.11
2,3	aDGlcp	99.62	72.24	73.63	77.40	71.55	61.37
2	aDGalf	103.19	75.55	80.87	80.87	71.55	63.78
	aLRhap	99.98	80.40	70.34	73.17	70.02	17.19

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize