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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: 28628892
Publication DOI: 10.1016/j.carres.2017.06.003
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: Evguenii.Vinogradov

nrc-cnrc.gc.ca
Institutions: National Research Council of Canada, Vaccine Program, Human Health Therapeutics, Ottawa Canada, K1A OR6

Cell surface polysaccharides produced by C. perfringens ATCC 13124 were analyzed using NMR, chemical and immunological methods. Two distinct polymers were identified. The more abundant PS1 had a structure based on a polymer of β-mannosamine with a number of modifications, including varying levels of substitution at O-6 with PEtN, N-acetylation, and different linkages between monosaccharides. The shortest variant of PS1 represented a lipoteichoic acid. It contained only 1-4-linkages between ManNAc residues, minor branching α-Ribf, and glucosyl-glycerol at the reducing end, which was acylated with linear saturated fatty acids C16, C18, and C20 (dominant). Other non-lipidated variants of PS1 contained less PEtN, no α-Ribf, up to 50% 1-3-linkages, and up to 25% ManN with the free amino group. The minor polysaccharide PS2 had a linear regular structure with a -4-α-Rha-3-β-Gal-4-β-GalNAc3PCho- repeating unit, where PCho indicates phosphocholine.

structure, polysaccharide, NMR spectroscopy, Clostridium perfringens

Structure type: oligomer
Location inside paper: p.92, fig.4, table 2, dephosphorylated pPS1
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_885813,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, NMR-2D, de-O-acylation, SDS-PAGE, sugar analysis, Western blotting, GPC, ion-exchange chromatography, HF treatment, N-acetylation, immunization, lysozyme treatment
Comments, role: dephosphorylated pPS1; the NMR solution was not indicated.

Related record ID(s): 11976, 12255, 12256, 12258, 12259
NCBI Taxonomy refs (TaxIDs): 195103
Reference(s) to other database(s): GTC:G24200SN
Show glycosyltransferases

NMR conditions: at 298 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
?,4,4,4,4,2	Ac	?	23.4
?,4,4,4,4	b?ManpN	100.6	54.4	73.0	67.8	77.7	61.5
?,4,4,4,2	Ac	?	23.4
?,4,4,4	b?ManpN	100.6	54.0	71.6	77.3	76.3	61.1
?,4,4,2	Ac	?	23.4
?,4,4	b?ManpN	100.4	53.8	71.6	77.3	76.3	61.1
?,4	b?ManpN	97.6	55.2	69.4	76.6	75.9	61.1
?	b?Glcp	103.5	74.1	74.9	79.1	75.6	61.1
	x?Gro	72.0	71.9	63.5


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
?,4,4,4,4,2	Ac	-	2.06
?,4,4,4,4	b?ManpN	4.85	4.55	3.82	3.51	3.43	3.80-3.92
?,4,4,4,2	Ac	-	2.06
?,4,4,4	b?ManpN	4.84	4.57	3.93	3.73	3.48	3.76-3.88
?,4,4,2	Ac	-	2.06
?,4,4	b?ManpN	4.89	4.60	3.95	3.74	3.54	3.78-3.89
?,4	b?ManpN	5.03	3.91	4.11	3.79	3.57	3.76-3.89
?	b?Glcp	4.48	3.36	3.68	3.76	3.59	3.73-3.89
	x?Gro	3.76-3.90	3.93	3.60-3.67


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
?,4,4,4,4,2	Ac		23.4/2.06
?,4,4,4,4	b?ManpN	100.6/4.85	54.4/4.55	73.0/3.82	67.8/3.51	77.7/3.43	61.5/3.80-3.92
?,4,4,4,2	Ac		23.4/2.06
?,4,4,4	b?ManpN	100.6/4.84	54.0/4.57	71.6/3.93	77.3/3.73	76.3/3.48	61.1/3.76-3.88
?,4,4,2	Ac		23.4/2.06
?,4,4	b?ManpN	100.4/4.89	53.8/4.60	71.6/3.95	77.3/3.74	76.3/3.54	61.1/3.78-3.89
?,4	b?ManpN	97.6/5.03	55.2/3.91	69.4/4.11	76.6/3.79	75.9/3.57	61.1/3.76-3.89
?	b?Glcp	103.5/4.48	74.1/3.36	74.9/3.68	79.1/3.76	75.6/3.59	61.1/3.73-3.89
	x?Gro	72.0/3.76-3.90	71.9/3.93	63.5/3.60-3.67

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
?,4,4,4,4,2	Ac		2.06
?,4,4,4,4	b?ManpN	4.85	4.55	3.82	3.51	3.43	3.80 3.92
?,4,4,4,2	Ac		2.06
?,4,4,4	b?ManpN	4.84	4.57	3.93	3.73	3.48	3.76 3.88
?,4,4,2	Ac		2.06
?,4,4	b?ManpN	4.89	4.60	3.95	3.74	3.54	3.78 3.89
?,4	b?ManpN	5.03	3.91	4.11	3.79	3.57	3.76 3.89
?	b?Glcp	4.48	3.36	3.68	3.76	3.59	3.73 3.89
	x?Gro	3.76 3.90	3.93	3.60 3.67

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
?,4,4,4,4,2	Ac	?	23.4
?,4,4,4,4	b?ManpN	100.6	54.4	73.0	67.8	77.7	61.5
?,4,4,4,2	Ac	?	23.4
?,4,4,4	b?ManpN	100.6	54.0	71.6	77.3	76.3	61.1
?,4,4,2	Ac	?	23.4
?,4,4	b?ManpN	100.4	53.8	71.6	77.3	76.3	61.1
?,4	b?ManpN	97.6	55.2	69.4	76.6	75.9	61.1
?	b?Glcp	103.5	74.1	74.9	79.1	75.6	61.1
	x?Gro	72.0	71.9	63.5

The spectrum also has 3 signals at unknown positions (not plotted).

There are 64 chemically distinct structures. Please, select:

CC(=O)N[C@@H]1[C@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](CO)O[C@@H](O[C@@H]4[C@@H](CO)O[C@@H](O[C@@H]5[C@@H](CO)O[C@@H](OCC(O)CO)[C@H](O)[C@H]5O)[C@@H](N)[C@H]4O)[C@@H](NC(C)=O)[C@H]3O)[C@@H](NC(C)=O)[C@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize