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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: dysentery [ICD11: SA56

]

The structure was elucidated in this paper
NCBI PubMed ID: 18954864
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: evguenii.vinogradov

nrc.ca (E. Vinogradov)
Institutions: National Institute of Child Health and Human Development, National Institutes of Health, 9000 Rockville Pike, Bethesda, MD, USA

Plesiomonas shigelloides O17 LPS contains the same O-antigenic polysaccharide chain as a causative agent of dysentery, Shigella sonnei. This polysaccharide can be used as a component of a vaccine against dysentery. Core part of the P. shigelloides O17 LPS was studied using NMR and mass spectrometry and the following structure was proposed: Significant similarity of the P. shigelloides O17 LPS core with the structure of the P. shigelloides O54 core was observed

NMR, LPS, structure, core, Shigella sonnei, O-chain, Plesiomonas, Plesiomonas shigelloides, conjugare vaccine

Structure type: oligomer
Location inside paper: p.3123, abstract, p.3125, scheme 1, 1
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130670,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137473,IEDB_140088,IEDB_141794,IEDB_141807,IEDB_142345,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_226811,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

Methods: 13C NMR, 1H NMR, methylation, GLC-MS, sugar analysis, GLC, mild acid hydrolysis, alkaline degradation, NMR-1D

Related record ID(s): 23027, 23028, 23029
NCBI Taxonomy refs (TaxIDs): 703
Reference(s) to other database(s): GTC:G48631IA, GlycomeDB:36871
Show glycosyltransferases

NMR conditions: in D2O at 308 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7
5,3,2	50%bDGlcp	104.1	74.6	76.0	70.4	76.5	61.9
5,3,3,4,6,4,3,2	Ac
5,3,3,4,6,4,3	aLAltpNA	102.2	52.7	69.4	70.5	79.2	176.2
5,3,3,4,6,4,2	Ac
5,3,3,4,6,4	bDFucpN4N	102.4	52.1	77.1	55.9	68.6	16.7
5,3,3,4,6,2	Ac
5,3,3,4,6	bDGlcpN	102.6	56.4	73.7	79.6	75.9	61.2
5,3,3,4	aDGlcpN	97.6	55.3	70.8	70.5	72.4	68.9
5,3,3	aDGalpA	102.6	69.9	68.9	81.0	72.9	176.5
5,3,7,7,4	aDGalpN	96.1	52.3	67.6	69.3	72.4	62.0
5,3,7,7	aDGalpA	100.0	69.3	70.3	78.3	71.3	177.2
5,3,7	aXLDmanHepp	103.2	71.5	71.8	67.2	73.7	68.8	72.2
5,3	aXLDmanHepp
5,4	bDGalp	104.8	72.2	73.8	69.8	76.4	62.9
5	aXLDmanHepp
	?XKdo?


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7
5,3,2	50%bDGlcp	4.61	3.24	3.53	3.47	3.63	3.81-3.91
5,3,3,4,6,4,3,2	Ac
5,3,3,4,6,4,3	aLAltpNA	4.90	3.99	3.67	4.39	4.41	-
5,3,3,4,6,4,2	Ac
5,3,3,4,6,4	bDFucpN4N	4.58	3.85	4.18	4.00	4.11	1.34
5,3,3,4,6,2	Ac
5,3,3,4,6	bDGlcpN	4.51	3.77	3.69	3.67	3.51	3.65-3.84
5,3,3,4	aDGlcpN	5.17	3.27	3.87	3.50	4.32	3.83-4.08
5,3,3	aDGalpA	5.46	3.86	4.22	4.43	4.59	-
5,3,7,7,4	aDGalpN	5.28	3.47	4.13	4.04	4.34	3.75-3.75
5,3,7,7	aDGalpA	5.03	3.95	4.08	4.52	4.32	-
5,3,7	aXLDmanHepp	4.92	3.96	3.86	3.90	3.63	4.24	3.64-3.83
5,3	aXLDmanHepp
5,4	bDGalp	4.42	3.58	3.66	3.89	3.68	3.68-3.71
5	aXLDmanHepp
	?XKdo?


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7
5,3,2	50%bDGlcp	104.1/4.61	74.6/3.24	76.0/3.53	70.4/3.47	76.5/3.63	61.9/3.81-3.91
5,3,3,4,6,4,3,2	Ac
5,3,3,4,6,4,3	aLAltpNA	102.2/4.90	52.7/3.99	69.4/3.67	70.5/4.39	79.2/4.41	
5,3,3,4,6,4,2	Ac
5,3,3,4,6,4	bDFucpN4N	102.4/4.58	52.1/3.85	77.1/4.18	55.9/4.00	68.6/4.11	16.7/1.34
5,3,3,4,6,2	Ac
5,3,3,4,6	bDGlcpN	102.6/4.51	56.4/3.77	73.7/3.69	79.6/3.67	75.9/3.51	61.2/3.65-3.84
5,3,3,4	aDGlcpN	97.6/5.17	55.3/3.27	70.8/3.87	70.5/3.50	72.4/4.32	68.9/3.83-4.08
5,3,3	aDGalpA	102.6/5.46	69.9/3.86	68.9/4.22	81.0/4.43	72.9/4.59	
5,3,7,7,4	aDGalpN	96.1/5.28	52.3/3.47	67.6/4.13	69.3/4.04	72.4/4.34	62.0/3.75-3.75
5,3,7,7	aDGalpA	100.0/5.03	69.3/3.95	70.3/4.08	78.3/4.52	71.3/4.32	
5,3,7	aXLDmanHepp	103.2/4.92	71.5/3.96	71.8/3.86	67.2/3.90	73.7/3.63	68.8/4.24	72.2/3.64-3.83
5,3	aXLDmanHepp
5,4	bDGalp	104.8/4.42	72.2/3.58	73.8/3.66	69.8/3.89	76.4/3.68	62.9/3.68-3.71
5	aXLDmanHepp
	?XKdo?

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7
5,3,2	50%bDGlcp	4.61	3.24	3.53	3.47	3.63	3.81 3.91
5,3,3,4,6,4,3,2	Ac
5,3,3,4,6,4,3	aLAltpNA	4.90	3.99	3.67	4.39	4.41
5,3,3,4,6,4,2	Ac
5,3,3,4,6,4	bDFucpN4N	4.58	3.85	4.18	4.00	4.11	1.34
5,3,3,4,6,2	Ac
5,3,3,4,6	bDGlcpN	4.51	3.77	3.69	3.67	3.51	3.65 3.84
5,3,3,4	aDGlcpN	5.17	3.27	3.87	3.50	4.32	3.83 4.08
5,3,3	aDGalpA	5.46	3.86	4.22	4.43	4.59
5,3,7,7,4	aDGalpN	5.28	3.47	4.13	4.04	4.34	3.75 3.75
5,3,7,7	aDGalpA	5.03	3.95	4.08	4.52	4.32
5,3,7	aXLDmanHepp	4.92	3.96	3.86	3.90	3.63	4.24	3.64 3.83
5,3	aXLDmanHepp
5,4	bDGalp	4.42	3.58	3.66	3.89	3.68	3.68 3.71
5	aXLDmanHepp
	?XKdo?

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7
5,3,2	50%bDGlcp	104.1	74.6	76.0	70.4	76.5	61.9
5,3,3,4,6,4,3,2	Ac
5,3,3,4,6,4,3	aLAltpNA	102.2	52.7	69.4	70.5	79.2	176.2
5,3,3,4,6,4,2	Ac
5,3,3,4,6,4	bDFucpN4N	102.4	52.1	77.1	55.9	68.6	16.7
5,3,3,4,6,2	Ac
5,3,3,4,6	bDGlcpN	102.6	56.4	73.7	79.6	75.9	61.2
5,3,3,4	aDGlcpN	97.6	55.3	70.8	70.5	72.4	68.9
5,3,3	aDGalpA	102.6	69.9	68.9	81.0	72.9	176.5
5,3,7,7,4	aDGalpN	96.1	52.3	67.6	69.3	72.4	62.0
5,3,7,7	aDGalpA	100.0	69.3	70.3	78.3	71.3	177.2
5,3,7	aXLDmanHepp	103.2	71.5	71.8	67.2	73.7	68.8	72.2
5,3	aXLDmanHepp
5,4	bDGalp	104.8	72.2	73.8	69.8	76.4	62.9
5	aXLDmanHepp
	?XKdo?

There are 2 chemically distinct structures. Please, select:

CC(=O)N[C@H]1[C@H](O[C@@H]2[C@@H](CO)O[C@@H](OC[C@H]3O[C@H](O[C@H]4[C@@H](C(=O)O)O[C@H](O[C@@H]5[C@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[C@@H](O[C@@H]6[C@H](O)[C@@H](O[C@@H]7[C@H](O)CC(O)(C(=O)O)O[C@@H]7[C@H](O)CO)O[C@H]([C@@H](O)CO)[C@H]6O[C@@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6O)O[C@H]([C@@H](O)CO[C@H]6O[C@H]([C@@H](O)CO[C@H]7O[C@H](C(=O)O)[C@H](O[C@H]8O[C@H](CO)[C@H](O)[C@H](O)[C@H]8N)[C@H](O)[C@H]7O)[C@@H](O)[C@H](O)[C@@H]6O)[C@H]5O)[C@H](O)[C@H]4O)[C@H](N)[C@@H](O)[C@@H]3O)[C@H](NC(C)=O)[C@H]2O)O[C@H](C)[C@H](N)[C@@H]1O[C@@H]1O[C@@H](C(=O)O)[C@H](O)[C@H](O)[C@H]1NC(C)=O

SVG MW SMILES 3D mol Ionize