CSDB: Search results

Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: diarrhea [ICD11: ME05.1

, ICD11: SA55

]

The structure was elucidated in this paper
NCBI PubMed ID: 23389090
Publication DOI: 10.3390/md11020440
Journal NLM ID: 101213729
Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: aniaaugustyniuk

iitd.pan.wroc.pl
Institutions: Department of Immunochemistry, Ludwik Hirszfeld Institute Immunology and Experimental Therapy, Polish Academy of Sciences, Rudolfa Wroclaw, Poland

The herein presented complete structure of the core oligosaccharide of lipopolysaccharide (LPS) P. shigelloides Polish Collection of Microorganisms (PCM) 2231 (serotype O17) was investigated by (1)H, (13)C NMR spectroscopy, mass spectrometry, chemical analyses and serological methods. The core oligosaccharide is composed of an undecasaccharide, which represents the second core type identified for P. shigelloides serotype O17 LPS. This structure is similar to that of the core oligosaccharide of P. shigelloides strains 302-73 (serotype O1) and 7-63 (serotype O17) and differs from these only by one sugar residue. Serological screening of 55 strains of P. shigelloides with the use of serum against identified core oligosaccharide conjugated with bovine serum albumin (BSA) indicated the presence of similar structures in the LPS core region of 28 O-serotypes. This observation suggests that the core oligosaccharide structure present in strain PCM 2231 could be the most common type among P. shigelloides lipopolysaccharides.

Lipopolysaccharide, core oligosaccharide, endotoxin, Plesiomonas shigelloides

Structure type: oligomer
Location inside paper: p.443, PSV
Compound class: core oligosaccharide with O-unit
Contained glycoepitopes: IEDB_130650,IEDB_130670,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,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, NMR-2D, GC-MS, SDS-PAGE, sugar analysis, mild acid hydrolysis, MALDI-TOF MS, NMR-1D, serological methods, immunoblotting, mild acid hydrolysismethylation
Comments, role: product from mild acid hydrolysis of the LPS

Related record ID(s): 29266, 29642, 29643
NCBI Taxonomy refs (TaxIDs): 703
Reference(s) to other database(s): GTC:G84852PY
Show glycosyltransferases

NMR conditions: in D2O at 300 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
5,3,2	%bDGlcp	103.5	74.0	75.4	69.9	76.2	61.3
5,3,3,4,6,4,3,2	Ac	175.3	23.0
5,3,3,4,6,4,3	aLAltpNA	101.7	52.2	68.8	69.9	78.7	175.4
5,3,3,4,6,4,2	Ac	174.7	23.0
5,3,3,4,6,4	bDFucpN4N	101.9	51.6	76.5	55.4	68.1	16.3
5,3,3,4,6,2	Ac	175.4	23.0
5,3,3,4,6	bDGlcpN	102.2	55.9	73.0	79.1	75.3	60.8
5,3,3,4	aDGlcpN	97.0	54.9	70.3	70.0	71.6	68.6
5,3,3	aDGalpA	102.1	69.2	69.0	80.1	72.3	175.6
5,3,7,7,4	%aDGlcpN	95.1	55.0	70.3	70.0	73.0	60.7
5,3,7,7	aDGalpA	99.7	68.8	69.7	77.3	70.6	176.5
5,3,7	aXLDmanHepp	103.2	70.9	71.2	66.7	73.2	68.4	72.0
5,3	aXLDmanHepp	99.7	78.9	79.3	66.4	73.2	69.1	73.6
5,4	bDGalp	104.2	72.2	73.1	71.0	75.8	62.6
5	aXLDmanHepp	101.3	71.1	75.3	75.1	72.0	69.2	63.8
	?XKdop	?	?	34.4	66.4	75.3	70.0	72.1	64.1


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
5,3,2	%bDGlcp	4.59	3.22	3.51	3.45	3.59	3.78-3.90
5,3,3,4,6,4,3,2	Ac	-	2.00
5,3,3,4,6,4,3	aLAltpNA	4.88	3.97	3.66	4.38	4.41	-
5,3,3,4,6,4,2	Ac	-	2.06
5,3,3,4,6,4	bDFucpN4N	4.57	3.83	4.16	3.98	4.09	1.32
5,3,3,4,6,2	Ac	-	2.06
5,3,3,4,6	bDGlcpN	4.48	3.75	3.68	3.65	3.49	3.63-3.82
5,3,3,4	aDGlcpN	5.12	3.26	3.86	3.47	4.33	3.79-4.08
5,3,3	aDGalpA	5.33	3.83	4.25	4.36	4.53	-
5,3,7,7,4	%aDGlcpN	5.24	3.22	3.91	3.50	4.11	3.81
5,3,7,7	aDGalpA	5.02	3.95	4.07	4.52	4.31	-
5,3,7	aXLDmanHepp	4.88	4.00	3.84	3.89	3.60	4.21	3.58-3.82
5,3	aXLDmanHepp	5.38	4.22	4.10	4.04	3.60	4.14	3.56-3.94
5,4	bDGalp	4.51	3.50	3.62	3.95	3.66	3.69-3.74
5	aXLDmanHepp	5.11	4.04	4.13	4.23	4.17	4.17	3.72
	?XKdop	-	-	1.86-2.22	4.12	4.13	3.70	3.86	3.60-3.84


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8
5,3,2	%bDGlcp	103.5/4.59	74.0/3.22	75.4/3.51	69.9/3.45	76.2/3.59	61.3/3.78-3.90
5,3,3,4,6,4,3,2	Ac		23.0/2.00
5,3,3,4,6,4,3	aLAltpNA	101.7/4.88	52.2/3.97	68.8/3.66	69.9/4.38	78.7/4.41	
5,3,3,4,6,4,2	Ac		23.0/2.06
5,3,3,4,6,4	bDFucpN4N	101.9/4.57	51.6/3.83	76.5/4.16	55.4/3.98	68.1/4.09	16.3/1.32
5,3,3,4,6,2	Ac		23.0/2.06
5,3,3,4,6	bDGlcpN	102.2/4.48	55.9/3.75	73.0/3.68	79.1/3.65	75.3/3.49	60.8/3.63-3.82
5,3,3,4	aDGlcpN	97.0/5.12	54.9/3.26	70.3/3.86	70.0/3.47	71.6/4.33	68.6/3.79-4.08
5,3,3	aDGalpA	102.1/5.33	69.2/3.83	69.0/4.25	80.1/4.36	72.3/4.53	
5,3,7,7,4	%aDGlcpN	95.1/5.24	55.0/3.22	70.3/3.91	70.0/3.50	73.0/4.11	60.7/3.81
5,3,7,7	aDGalpA	99.7/5.02	68.8/3.95	69.7/4.07	77.3/4.52	70.6/4.31	
5,3,7	aXLDmanHepp	103.2/4.88	70.9/4.00	71.2/3.84	66.7/3.89	73.2/3.60	68.4/4.21	72.0/3.58-3.82
5,3	aXLDmanHepp	99.7/5.38	78.9/4.22	79.3/4.10	66.4/4.04	73.2/3.60	69.1/4.14	73.6/3.56-3.94
5,4	bDGalp	104.2/4.51	72.2/3.50	73.1/3.62	71.0/3.95	75.8/3.66	62.6/3.69-3.74
5	aXLDmanHepp	101.3/5.11	71.1/4.04	75.3/4.13	75.1/4.23	72.0/4.17	69.2/4.17	63.8/3.72
	?XKdop			34.4/1.86-2.22	66.4/4.12	75.3/4.13	70.0/3.70	72.1/3.86	64.1/3.60-3.84

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
5,3,2	%bDGlcp	4.59	3.22	3.51	3.45	3.59	3.78 3.90
5,3,3,4,6,4,3,2	Ac		2.00
5,3,3,4,6,4,3	aLAltpNA	4.88	3.97	3.66	4.38	4.41
5,3,3,4,6,4,2	Ac		2.06
5,3,3,4,6,4	bDFucpN4N	4.57	3.83	4.16	3.98	4.09	1.32
5,3,3,4,6,2	Ac		2.06
5,3,3,4,6	bDGlcpN	4.48	3.75	3.68	3.65	3.49	3.63 3.82
5,3,3,4	aDGlcpN	5.12	3.26	3.86	3.47	4.33	3.79 4.08
5,3,3	aDGalpA	5.33	3.83	4.25	4.36	4.53
5,3,7,7,4	%aDGlcpN	5.24	3.22	3.91	3.50	4.11	3.81
5,3,7,7	aDGalpA	5.02	3.95	4.07	4.52	4.31
5,3,7	aXLDmanHepp	4.88	4.00	3.84	3.89	3.60	4.21	3.58 3.82
5,3	aXLDmanHepp	5.38	4.22	4.10	4.04	3.60	4.14	3.56 3.94
5,4	bDGalp	4.51	3.50	3.62	3.95	3.66	3.69 3.74
5	aXLDmanHepp	5.11	4.04	4.13	4.23	4.17	4.17	3.72
	?XKdop			1.86 2.22	4.12	4.13	3.70	3.86	3.60 3.84

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
5,3,2	%bDGlcp	103.5	74.0	75.4	69.9	76.2	61.3
5,3,3,4,6,4,3,2	Ac	175.3	23.0
5,3,3,4,6,4,3	aLAltpNA	101.7	52.2	68.8	69.9	78.7	175.4
5,3,3,4,6,4,2	Ac	174.7	23.0
5,3,3,4,6,4	bDFucpN4N	101.9	51.6	76.5	55.4	68.1	16.3
5,3,3,4,6,2	Ac	175.4	23.0
5,3,3,4,6	bDGlcpN	102.2	55.9	73.0	79.1	75.3	60.8
5,3,3,4	aDGlcpN	97.0	54.9	70.3	70.0	71.6	68.6
5,3,3	aDGalpA	102.1	69.2	69.0	80.1	72.3	175.6
5,3,7,7,4	%aDGlcpN	95.1	55.0	70.3	70.0	73.0	60.7
5,3,7,7	aDGalpA	99.7	68.8	69.7	77.3	70.6	176.5
5,3,7	aXLDmanHepp	103.2	70.9	71.2	66.7	73.2	68.4	72.0
5,3	aXLDmanHepp	99.7	78.9	79.3	66.4	73.2	69.1	73.6
5,4	bDGalp	104.2	72.2	73.1	71.0	75.8	62.6
5	aXLDmanHepp	101.3	71.1	75.3	75.1	72.0	69.2	63.8
	?XKdop	?	?	34.4	66.4	75.3	70.0	72.1	64.1

The spectrum also has 2 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

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