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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: Gallus gallus; Bos taurus
Associated disease: fowl cholera [ICD11: XN30D

]; hemorrhagic septicemia [ICD11: MA15.Y

]; infection due to Pasteurella multocida [ICD11: XN30D

]

The structure was elucidated in this paper
NCBI PubMed ID: 24740556
Publication DOI: 10.1093/glycob/cwu030
Journal NLM ID: 9104124
Publisher: IRL Press at Oxford University Press
Correspondence: marina.harper

monash.edu
Institutions: Australian Research Council Centre of Excellence in Structural and Functional Microbial Genomics, Monash University, Melbourne, Australia

Pasteurella multocida is a Gram-negative bacterial pathogen classified into 16 serovars based on lipopolysaccharide (LPS) antigens. Previously, we have characterised the LPS outer core biosynthesis loci L1, L2, L3, L5 and L7, and have elucidated the full range of LPS structures associated with each. In this study, we have determined the LPS structures produced by the type strains representing the serovars 10, 11, 12 and 15 and characterized a new LPS outer core biosynthesis locus, L6, common to all. The L6 outer core biosynthesis locus shares significant synteny with the L3 locus but due to nucleotide divergence, gene duplication, and gene redundancy, the L6 and L3 LPS outer cores are structurally distinct. Using LPS structural and genetic differences identified in each L6 strain we have predicted a role for most of the L6 glycosyltransferases in LPS assembly. Importantly, we have identified two glycosyltransferases, GctD and GatB, that differ by one amino acid, A162T, but use different donor sugars (UDP-Glc and UDP-Gal respectively). The longest outer core oligosaccharide, produced by the serovar 12 type strain, contained a terminal region consisting of β-Gal-(1,4)-β-GlcNAc-(1,3)-β-Gal-(1,4)-β-Glc that was identical in structure to the vertebrate glycosphingolipid, paragloboside. Mimicry of host glycosphingolipids has been observed previously in P. multocida strains belonging to L3 LPS genotype, which produce LPS similar in structure to the globo-series of glycosphingolipids. The expression of a paragloboside-like oligosaccharide on the LPS produced by the serovar 12 type strain indicates that strains belonging to the L6 LPS genotype may also engage in molecular mimicry.

LPS, structure, gene, genetics, core oligosaccharide, glycosyltransferases, glycosyltransferase, Pasteurella multocida, glycosphingolipid

Structure type: oligomer
Location inside paper: p.652, p.654, fig.2, serovar 12 (P1573)
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130646,IEDB_130650,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_1391966,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140110,IEDB_140122,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_149144,IEDB_151531,IEDB_190606,IEDB_2189047,IEDB_983931,SB_145,SB_165,SB_166,SB_173,SB_187,SB_192,SB_195,SB_30,SB_6,SB_7,SB_88

Methods: 13C NMR, 1H NMR, GLC-MS, PCR, de-O-acylation, sugar analysis, DNA techniques, genetic methods, biochemical methods, CE-ESI-MS, bioinformatic analysis
Comments, role: NMR data for the completely deacylated LPS from Pasteurella multocida serovar 12 strain P1573

Related record ID(s): 30256, 30257, 30258, 30259
NCBI Taxonomy refs (TaxIDs): 747
Reference(s) to other database(s): GTC:G65581OG
Show glycosyltransferases

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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7
5,3,2	aXLDmanHepp	101.7	70.2	71.0	66.3	71.6	70.6	?
5,3,3,0	xXEtN
5,3,3	P
5,3	aXLDmanHepp	100.3	80.5	75.9	67.2	73.3	70.0	64.4
5,4,6,6,4,3,4	bDGalp	103.2	71.3	72.7	68.6	75.5	62.4
5,4,6,6,4,3,2	Ac
5,4,6,6,4,3	bDGlcpN	101.6	57.2	72.1	79.4	76.5	61.1
5,4,6,6,4	bDGalp	104.0	71.6	83.2	69.9	76.9	62.4
5,4,6,6	bDGlcp	104.9	74.5	75.5	79.4	76.1	61.5
5,4,6	aXLDmanHepp	101.4	71.0	72.0	67.7	73.1	80.5	64.1
5,4	bDGlcp	104.8	74.9	78.4	70.9	75.2	66.2
5,6	aDGlcp	102.9	73.7	74.5	70.1	73.1	61.0
5	aXLDmanHepp	100.7	71.6	74.7	75.6	73.0	82.0	64.9
4,0,0	xXEtN
4,0	%xXP?
4	P
	aXKdop


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7
5,3,2	aXLDmanHepp	5.21	4.00	3.87	3.82	3.78	4.08	?
5,3,3,0	xXEtN
5,3,3	P
5,3	aXLDmanHepp	5.75	4.32	4.46	4.08	3.67	4.08	3.61-3.72
5,4,6,6,4,3,4	bDGalp	4.47	3.54	3.67	3.93	3.74	3.74-3.79
5,4,6,6,4,3,2	Ac
5,4,6,6,4,3	bDGlcpN	5.02	3.18	3.87	3.78	3.65	3.88-3.96
5,4,6,6,4	bDGalp	4.52	3.72	3.90	4.20	3.74	3.74-3.79
5,4,6,6	bDGlcp	4.57	3.44	3.67	3.72	3.64	3.81-3.98
5,4,6	aXLDmanHepp	5.05	4.04	3.81	3.95	3.90	4.17	3.74-3.90
5,4	bDGlcp	4.59	3.52	3.40	3.61	3.49	3.72-4.07
5,6	aDGlcp	5.21	3.57	3.83	3.56	3.94	3.76-3.96
5	aXLDmanHepp	5.17	4.14	4.02	4.18	4.19	4.07	3.70
4,0,0	xXEtN
4,0	%xXP?
4	P
	aXKdop


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7
5,3,2	aXLDmanHepp	101.7/5.21	70.2/4.00	71.0/3.87	66.3/3.82	71.6/3.78	70.6/4.08	?/?
5,3,3,0	xXEtN
5,3,3	P
5,3	aXLDmanHepp	100.3/5.75	80.5/4.32	75.9/4.46	67.2/4.08	73.3/3.67	70.0/4.08	64.4/3.61-3.72
5,4,6,6,4,3,4	bDGalp	103.2/4.47	71.3/3.54	72.7/3.67	68.6/3.93	75.5/3.74	62.4/3.74-3.79
5,4,6,6,4,3,2	Ac
5,4,6,6,4,3	bDGlcpN	101.6/5.02	57.2/3.18	72.1/3.87	79.4/3.78	76.5/3.65	61.1/3.88-3.96
5,4,6,6,4	bDGalp	104.0/4.52	71.6/3.72	83.2/3.90	69.9/4.20	76.9/3.74	62.4/3.74-3.79
5,4,6,6	bDGlcp	104.9/4.57	74.5/3.44	75.5/3.67	79.4/3.72	76.1/3.64	61.5/3.81-3.98
5,4,6	aXLDmanHepp	101.4/5.05	71.0/4.04	72.0/3.81	67.7/3.95	73.1/3.90	80.5/4.17	64.1/3.74-3.90
5,4	bDGlcp	104.8/4.59	74.9/3.52	78.4/3.40	70.9/3.61	75.2/3.49	66.2/3.72-4.07
5,6	aDGlcp	102.9/5.21	73.7/3.57	74.5/3.83	70.1/3.56	73.1/3.94	61.0/3.76-3.96
5	aXLDmanHepp	100.7/5.17	71.6/4.14	74.7/4.02	75.6/4.18	73.0/4.19	82.0/4.07	64.9/3.70
4,0,0	xXEtN
4,0	%xXP?
4	P
	aXKdop

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7
5,3,2	aXLDmanHepp	5.21	4.00	3.87	3.82	3.78	4.08	?
5,3,3,0	xXEtN
5,3,3	P
5,3	aXLDmanHepp	5.75	4.32	4.46	4.08	3.67	4.08	3.61 3.72
5,4,6,6,4,3,4	bDGalp	4.47	3.54	3.67	3.93	3.74	3.74 3.79
5,4,6,6,4,3,2	Ac
5,4,6,6,4,3	bDGlcpN	5.02	3.18	3.87	3.78	3.65	3.88 3.96
5,4,6,6,4	bDGalp	4.52	3.72	3.90	4.20	3.74	3.74 3.79
5,4,6,6	bDGlcp	4.57	3.44	3.67	3.72	3.64	3.81 3.98
5,4,6	aXLDmanHepp	5.05	4.04	3.81	3.95	3.90	4.17	3.74 3.90
5,4	bDGlcp	4.59	3.52	3.40	3.61	3.49	3.72 4.07
5,6	aDGlcp	5.21	3.57	3.83	3.56	3.94	3.76 3.96
5	aXLDmanHepp	5.17	4.14	4.02	4.18	4.19	4.07	3.70
4,0,0	xXEtN
4,0	%xXP?
4	P
	aXKdop

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7
5,3,2	aXLDmanHepp	101.7	70.2	71.0	66.3	71.6	70.6	?
5,3,3,0	xXEtN
5,3,3	P
5,3	aXLDmanHepp	100.3	80.5	75.9	67.2	73.3	70.0	64.4
5,4,6,6,4,3,4	bDGalp	103.2	71.3	72.7	68.6	75.5	62.4
5,4,6,6,4,3,2	Ac
5,4,6,6,4,3	bDGlcpN	101.6	57.2	72.1	79.4	76.5	61.1
5,4,6,6,4	bDGalp	104.0	71.6	83.2	69.9	76.9	62.4
5,4,6,6	bDGlcp	104.9	74.5	75.5	79.4	76.1	61.5
5,4,6	aXLDmanHepp	101.4	71.0	72.0	67.7	73.1	80.5	64.1
5,4	bDGlcp	104.8	74.9	78.4	70.9	75.2	66.2
5,6	aDGlcp	102.9	73.7	74.5	70.1	73.1	61.0
5	aXLDmanHepp	100.7	71.6	74.7	75.6	73.0	82.0	64.9
4,0,0	xXEtN
4,0	%xXP?
4	P
	aXKdop

The spectrum also has 1 signal at unknown position (not plotted).

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize