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Taxonomic group: bacteria / Firmicutes (Phylum: Firmicutes)
Associated disease: infection due to Clostridium perfringens [ICD11: XN7J5

]

The structure was elucidated in this paper
NCBI PubMed ID: 9534227
Publication DOI: 10.1016/S0008-6215(97)00280-2
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: cherniak

gsu.edu
Institutions: Department of Chemistry,Georgia State Univetsity, Atlanta,USA

The complete primary structure of the type-specific capsular polysaccharide of Clostridium perfringens Hobbs 10 was determined. The polysaccharide was isolated from C. perfringens Hobbs 10 by cold-water extraction of whole, heavily encapsulated cells. The polysaccharide was purified, by ethanol precipitation, deproteination, selective precipitation with hexadecyltrimethylammonium bromide, ion-exchange chromatography and gel-filtration chromatography. The polysaccharide was comprised of D-glucose, D-galactose, N-acetylgalactosamine, and iduronic acid, in molar ratios of 2:2:1:1. Sequence and linkage assignments of the glycosyl residues were obtained by NMR spectroscopy, specifically by the combination of two-dimensional homonuclear DQF-COSY, TQF-COSY and TOCSY, heteronuclear ¿1H, 13C¿ single-quantum coherence (HSQC) and heteronuclear multiple-bond correlation (HMBC) experiments. The capsular polysaccharide of C. perfringens Hobbs 10 is a polymer composed of a hexasaccharide repeating unit with the following structure: [formula: see text] This structure is novel among bacterial cell-surface polysaccharides, and it is only the second of many serotypically distinct capsular polysaccharides of C. perfringens to be described.

antigen, polysaccharide structure, 2D NMR spectroscopy, HMBC, TOCSY, Clostridium perfringens, DQF-COSY, TQF-COSY, HSQC

Structure type: polymer chemical repeating unit
Location inside paper: Abstract
Compound class: CPS
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130648,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_138950,IEDB_141495,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_146664,IEDB_149558,IEDB_151528,IEDB_190606,IEDB_742249,IEDB_918314,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_25,SB_6,SB_7,SB_87,SB_88

Methods: NMR

NCBI Taxonomy refs (TaxIDs): 1502
Reference(s) to other database(s): GTC:G26058IJ, GlycomeDB:26384
Show glycosyltransferases

NMR conditions: in D2O at 333 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4,4,3	aDGalp	98.42	71.05	71.84	79.58	72.84	63.10
3,4,4	bDGalp	105.57	72.06	80.22	67.54	77.50	63.39
3,4	bDGlcp	105.86	75.64	76.57	81.30	77.36	62.75
3	a?IdopA	105.79	72.92	73.70	82.44	72.70	177
2	Ac
6	bDGlcp	105.57	75.64	78.36	72.27	78.43	63.39
	bDGalpN	105.07	54.01	80.94	70.41	76.00	71.84


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,4,4,3	aDGalp	5.08	3.72	4.03	4.18	4.16	3.70-3.80
3,4,4	bDGalp	4.48	3.63	3.72	4.12	3.68	3.74-3.78
3,4	bDGlcp	4.55	3.33	3.63	3.63	3.59	3.78-3.96
3	a?IdopA	4.99	3.52	3.91	4.06	4.53	-
2	Ac
6	bDGlcp	4.46	3.27	3.46	3.37	3.42	3.70-3.89
	bDGalpN	4.71	4.03	3.85	4.00	3.85	3.91-4.00


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,4,4,3	aDGalp	98.42/5.08	71.05/3.72	71.84/4.03	79.58/4.18	72.84/4.16	63.10/3.70-3.80
3,4,4	bDGalp	105.57/4.48	72.06/3.63	80.22/3.72	67.54/4.12	77.50/3.68	63.39/3.74-3.78
3,4	bDGlcp	105.86/4.55	75.64/3.33	76.57/3.63	81.30/3.63	77.36/3.59	62.75/3.78-3.96
3	a?IdopA	105.79/4.99	72.92/3.52	73.70/3.91	82.44/4.06	72.70/4.53	
2	Ac
6	bDGlcp	105.57/4.46	75.64/3.27	78.36/3.46	72.27/3.37	78.43/3.42	63.39/3.70-3.89
	bDGalpN	105.07/4.71	54.01/4.03	80.94/3.85	70.41/4.00	76.00/3.85	71.84/3.91-4.00

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,4,4,3	aDGalp	5.08	3.72	4.03	4.18	4.16	3.70 3.80
3,4,4	bDGalp	4.48	3.63	3.72	4.12	3.68	3.74 3.78
3,4	bDGlcp	4.55	3.33	3.63	3.63	3.59	3.78 3.96
3	a?IdopA	4.99	3.52	3.91	4.06	4.53
2	Ac
6	bDGlcp	4.46	3.27	3.46	3.37	3.42	3.70 3.89
	bDGalpN	4.71	4.03	3.85	4.00	3.85	3.91 4.00

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4,4,3	aDGalp	98.42	71.05	71.84	79.58	72.84	63.10
3,4,4	bDGalp	105.57	72.06	80.22	67.54	77.50	63.39
3,4	bDGlcp	105.86	75.64	76.57	81.30	77.36	62.75
3	a?IdopA	105.79	72.92	73.70	82.44	72.70	177
2	Ac
6	bDGlcp	105.57	75.64	78.36	72.27	78.43	63.39
	bDGalpN	105.07	54.01	80.94	70.41	76.00	71.84

There are 2 chemically distinct structures. Please, select:

*O[C@H]1[C@@H](CO)O[C@H](O[C@H]2[C@@H](O)[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](CO)O[C@@H](O[C@H]4[C@@H](C(=O)O)O[C@H](O[C@@H]5[C@@H](NC(C)=O)[C@H](*)O[C@H](CO[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[C@@H]5O)[C@@H](O)[C@@H]4O)[C@H](O)[C@H]3O)[C@@H]2O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize