Vibriosis caused by Vibrio anguillarum affects salmonid and marine fish species worldwide and is considered to be one of the most serious threats to the success of commercial fish farming. In the course of this study, it was found that V. anguillarum serotype O:2 strains produce an acidic capsular polysaccharide having the identical structure to that of the O-chain polysaccharide. One-dimensional and two-dimensional nuclear magnetic resonance techniques, together with partial hydrolysis and various specific modifications, were used to determine the structure of these polysaccharides. It is proposed that both O-chain and capsular polysaccharide of V. anguillarum serotype O:2 are composed of linear tetrasaccharide repeating units having the following structure, in which Glc2NAc3NAN represents 2-acetamido-3-amino-2,3-dideoxy-D-glucuronamide, Man2NAc3AmA is 3-acetamidino-2-acetamido-2,3-dideoxy-D-mannuronic acid. Am represents an acetamidino group, Gal(NAc)2A is 2,3-diacetamido-2,3-dideoxy-L-galacturonic acid, Bac(NAc)2 is 2,4-diacetamido-2,4,6-trideoxy-D-glucose (N,N'-diacetylbacillosamine) and Fo is formyl

Lipopolysaccharide, LPS, structural, capsular, polysaccharide, serotype, O-antigen, O antigen, acid, capsular polysaccharide, structural studies, 2, 4-diacetamido-2, 4, Vibrio, 3-diamino-2, lipopolysaccharide O-antigen, 6-trideoxy-D-glucose, formyl, amide, 3-diacetamido-2, 3-dideoxy-D-glucuronic acid, 3-dideoxy-L-galacturonic acid, 3-dideoxy-D-mannuronic acid, N-acetimidoyl, N-formyl, Vibrio anguillarum

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,4,4,2	Ac	175	23.19
3,4,4,3,2	Fo	164.3
3,4,4,3	xLAla?	175	49.22	18.91
3,4,4,6	NH2
3,4,4	bDGlcpN3NA	102.27	54.19	53.50	76.0	76.10	171.9
3,4,2	Ac	175	22.82
3,4,3	Ac	176.1	22.82
3,4	bDManpN3NA	100.06	52.45	52.22	76.67	77.23	175
3,2	Ac	175	22.98
3,3	Ac	175	23.31
3	aLGalpN3NA	98.63	44.24	50.71	76.10	67.84	175
2	Ac	174.5	23.18
4	Ac	175	23.09
	bDQuipN4N	101.09	56.81	79.29	56.09	71.28	17.87


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,4,4,2	Ac	-	1.96
3,4,4,3,2	Fo	8.08
3,4,4,3	xLAla?	-	4.40	1.30
3,4,4,6	NH2
3,4,4	bDGlcpN3NA	4.59	3.72	4.05	3.86	3.97	-
3,4,2	Ac	-	1.89
3,4,3	Ac	-	2.07
3,4	bDManpN3NA	4.84	4.06	4.37	3.75	3.78	-
3,2	Ac	-	1.98
3,3	Ac	-	2.07
3	aLGalpN3NA	5.06	4.39	4.27	4.15	4.06	-
2	Ac	-	1.92
4	Ac	-	1.96
	bDQuipN4N	4.30	3.80	3.75	3.73	3.46	1.19


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,4,4,2	Ac		23.19/1.96
3,4,4,3,2	Fo	164.3/8.08
3,4,4,3	xLAla?		49.22/4.40	18.91/1.30
3,4,4,6	NH2
3,4,4	bDGlcpN3NA	102.27/4.59	54.19/3.72	53.50/4.05	76.0/3.86	76.10/3.97	
3,4,2	Ac		22.82/1.89
3,4,3	Ac		22.82/2.07
3,4	bDManpN3NA	100.06/4.84	52.45/4.06	52.22/4.37	76.67/3.75	77.23/3.78	
3,2	Ac		22.98/1.98
3,3	Ac		23.31/2.07
3	aLGalpN3NA	98.63/5.06	44.24/4.39	50.71/4.27	76.10/4.15	67.84/4.06	
2	Ac		23.18/1.92
4	Ac		23.09/1.96
	bDQuipN4N	101.09/4.30	56.81/3.80	79.29/3.75	56.09/3.73	71.28/3.46	17.87/1.19

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

*O[C@@H]1[C@@H](C(N)=O)O[C@@H](O[C@@H]2[C@@H](C(=O)O)O[C@@H](O[C@H]3[C@@H](NC(C)=O)[C@H](NC(C)=O)[C@H](O[C@@H]4[C@@H](NC(C)=O)[C@H](*)O[C@H](C)[C@H]4NC(C)=O)O[C@H]3C(=O)O)[C@@H](NC(C)=O)[C@H]2NC(C)=O)[C@H](NC(C)=O)[C@H]1NC(=O)[C@H](C)NC=O

1059.006 g/mol (C₄₂H₆₂R₂N₁₀O₂₂, R = next and previous repeats, not counted in mol weight)