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

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

*O[C@H]1[C@H](C(=O)O)O[C@@H](O[C@@H]2[C@@H](NC(C)=O)[C@H](*)O[C@H](C)[C@@H]2N)[C@H](NC(C)=O)[C@H]1O

403.388 g/mol (C₁₆H₂₅R₂N₃O₉, R = next and previous repeats, not counted in mol weight)

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

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

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

1813.537 g/mol (C₆₅H₁₀₈N₂O₅₆)

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

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

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

2016.731 g/mol (C₇₃H₁₂₁N₃O₆₁)

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

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

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

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

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

2420.119 g/mol (C₈₉H₁₄₆N₆O₇₀)