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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: (Actinopterygii)
Associated disease: edwardsiellosis

The structure was elucidated in this paper
NCBI PubMed ID: 36902212
Publication DOI: 10.3390/ijms24054768
Journal NLM ID: 101092791
Publisher: Basel, Switzerland: MDPI
Correspondence: S. Merino <smerino

ub.edu>; M. Kaszowska <marta.kaszowska

hirszfeld.pl>
Institutions: Laboratory of Microbial Immunochemistry and Vaccines, Ludwik Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, 53-114 Wroclaw, Poland, Department of Genetic, Microbiology and Statistic, University of Barcelona, Diagonal 643, 08028 Barcelona, Spain

The Edwardsiella genus presents five different pathogenic species: Edwardsiella tarda, E. anguillarum, E. piscicida, E. hoshinae and E. ictaluri. These species cause infections mainly in fish, but they can also infect reptiles, birds or humans. Lipopolysaccharide (endotoxin) plays an important role in the pathogenesis of these bacteria. For the first time, the chemical structure and genomics of the lipopolysaccharide (LPS) core oligosaccharides of E. piscicida, E. anguillarum, E. hoshinae and E. ictaluri were studied. The complete gene assignments for all core biosynthesis gene functions were acquired. The structure of core oligosaccharides was investigated by ¹H and 13C nuclear magnetic resonance (NMR) spectroscopy. The structures of E. piscicida and E. anguillarum core oligosaccharides show the presence of →3,4)-L-glycero-α-D-manno-Hepp, two terminal β-D-Glcp, →2,3,7)-L-glycero-α-D-manno-Hepp, →7)-L-glycero-α-D-manno-Hepp, terminal α-D-GlcpN, two →4)-α-D-GalpA, →3)-α-D-GlcpNAc, terminal β-D-Galp and →5-substituted Kdo. E. hoshinare core oligosaccharide shows only one terminal β-D-Glcp, and instead of terminal β-D-Galp a terminal α-D-GlcpNAc. E. ictaluri core oligosaccharide shows only one terminal β-D-Glcp, one →4)-α-D-GalpA and do not have terminal α-D-GlcpN (see complementary figure)

core oligosaccharide, NMR spectroscopy, genomic, Edwardsiellaea

Structure type: oligomer
Location inside paper: Fig. 6, table 3, Fig. 9(2), E. ictaluri OSVII
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130670,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141794,IEDB_141807,IEDB_142078,IEDB_142488,IEDB_146664,IEDB_150899,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_226811,IEDB_983931,SB_137,SB_165,SB_166,SB_187,SB_192,SB_195,SB_29,SB_7,SB_88

Methods: 13C NMR, 1H NMR, 31P NMR, SDS-Tricine-PAGE, phylogenetic analysis, computer analysis with Sparky, DEPT, genome analysis
Biosynthesis and genetic data: WabK, WabN,WabH, WabG, [WaaQ]WaaF, [WapE]WaaC
Comments, role: the positions of glycine in core oligosaccharide (OSVII) was not determined

Related record ID(s): 20288, 20289, 20290, 22252
NCBI Taxonomy refs (TaxIDs): 67780
Show glycosyltransferases

NMR conditions: in D2O at 298 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
5,3,3,4,3	bDGalp	103.7	71.5	73.3	69.2	75.9	61.1
5,3,3,4,2	Ac	175.2	22.6
5,3,3,4,?	xXGly	168.4	41.6
5,3,3,4	aDGlcpN	98.4	54.3	79.2	71.1	71.3	60.4
5,3,3	aDGalpA	100.8	69.7	68.7	77.9	71.3	175.1
5,3,7	aXLDmanHepp	101.5	70.7	72.7	69.3	71.1	69.3	63.9
5,3	aXLDmanHepp	99.1	68.4	76.3	67.4	71.0	69.5	70.8
5,4	bDGlcp	103.3	73.4	75.8	69.7	76.9	61.2
5	aXLDmanHepp	101.2	70.4	75.2	76.1	71.0	69.5	63.8
	aXKdo?	?	?	34.1	64.6	74.7	71.1	66.9	63.8


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
5,3,3,4,3	bDGalp	4.54	3.62	3.72	3.97	3.67	3.70-3.73
5,3,3,4,2	Ac	-	2.19
5,3,3,4,?	xXGly	-	3.90-4.09
5,3,3,4	aDGlcpN	5.00	4.06	3.84	4.01	4.30	3.82-3.96
5,3,3	aDGalpA	5.57	3.93	4.18	4.11	4.76	-
5,3,7	aXLDmanHepp	4.96	4.00	3.96	3.97	3.87	4.13	3.72-3.92
5,3	aXLDmanHepp	5.36	4.26	4.18	4.11	3.79	4.05	3.67-3.89
5,4	bDGlcp	4.48	3.33	3.52	3.52	3.40	3.75-3.88
5	aXLDmanHepp	5.18	4.15	4.25	4.28	4.11	4.11	3.79
	aXKdo?	-	-	1.92-2.27	4.14	4.14	4.01	3.92	3.69-3.89


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8
5,3,3,4,3	bDGalp	103.7/4.54	71.5/3.62	73.3/3.72	69.2/3.97	75.9/3.67	61.1/3.70-3.73
5,3,3,4,2	Ac		22.6/2.19
5,3,3,4,?	xXGly		41.6/3.90-4.09
5,3,3,4	aDGlcpN	98.4/5.00	54.3/4.06	79.2/3.84	71.1/4.01	71.3/4.30	60.4/3.82-3.96
5,3,3	aDGalpA	100.8/5.57	69.7/3.93	68.7/4.18	77.9/4.11	71.3/4.76	
5,3,7	aXLDmanHepp	101.5/4.96	70.7/4.00	72.7/3.96	69.3/3.97	71.1/3.87	69.3/4.13	63.9/3.72-3.92
5,3	aXLDmanHepp	99.1/5.36	68.4/4.26	76.3/4.18	67.4/4.11	71.0/3.79	69.5/4.05	70.8/3.67-3.89
5,4	bDGlcp	103.3/4.48	73.4/3.33	75.8/3.52	69.7/3.52	76.9/3.40	61.2/3.75-3.88
5	aXLDmanHepp	101.2/5.18	70.4/4.15	75.2/4.25	76.1/4.28	71.0/4.11	69.5/4.11	63.8/3.79
	aXKdo?			34.1/1.92-2.27	64.6/4.14	74.7/4.14	71.1/4.01	66.9/3.92	63.8/3.69-3.89

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
5,3,3,4,3	bDGalp	4.54	3.62	3.72	3.97	3.67	3.70 3.73
5,3,3,4,2	Ac		2.19
5,3,3,4,?	xXGly		3.90 4.09
5,3,3,4	aDGlcpN	5.00	4.06	3.84	4.01	4.30	3.82 3.96
5,3,3	aDGalpA	5.57	3.93	4.18	4.11	4.76
5,3,7	aXLDmanHepp	4.96	4.00	3.96	3.97	3.87	4.13	3.72 3.92
5,3	aXLDmanHepp	5.36	4.26	4.18	4.11	3.79	4.05	3.67 3.89
5,4	bDGlcp	4.48	3.33	3.52	3.52	3.40	3.75 3.88
5	aXLDmanHepp	5.18	4.15	4.25	4.28	4.11	4.11	3.79
	aXKdo?			1.92 2.27	4.14	4.14	4.01	3.92	3.69 3.89

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
5,3,3,4,3	bDGalp	103.7	71.5	73.3	69.2	75.9	61.1
5,3,3,4,2	Ac	175.2	22.6
5,3,3,4,?	xXGly	168.4	41.6
5,3,3,4	aDGlcpN	98.4	54.3	79.2	71.1	71.3	60.4
5,3,3	aDGalpA	100.8	69.7	68.7	77.9	71.3	175.1
5,3,7	aXLDmanHepp	101.5	70.7	72.7	69.3	71.1	69.3	63.9
5,3	aXLDmanHepp	99.1	68.4	76.3	67.4	71.0	69.5	70.8
5,4	bDGlcp	103.3	73.4	75.8	69.7	76.9	61.2
5	aXLDmanHepp	101.2	70.4	75.2	76.1	71.0	69.5	63.8
	aXKdo?	?	?	34.1	64.6	74.7	71.1	66.9	63.8

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

There are 2 chemically distinct structures. Please, select:

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

SVG MW SMILES 3D mol Ionize