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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: 25298538
Publication DOI: 10.1093/glycob/cwu110
Journal NLM ID: 9104124
Publisher: IRL Press at Oxford University Press
Correspondence: marina.harper

monash.edu
Institutions: Department of Microbiology, Australian Research Council Centre of Excellence in Structural and Functional Microbial Genomics, Vaccine Program, Human Health Therapeutics Portfolio, National Research Council, Ottawa, ON, Canada K1A 0R6, Department of Microbiology, Monash University, Building 76, Melbourne, Australia

Pasteurella multocida is an important veterinary pathogen that produces a wide range of lipopolysaccharide (LPS) structures, many of which mimic host glycoproteins. In this study, we complete our analysis of the LPS produced by the P. multocida Heddleston serovars by reporting the LPS structure and the LPS outer core biosynthesis loci of the type strains representing Heddleston serovars 6, 7 and 16. Genetic analysis revealed that the type strains representing serovars 6 and 7 share the same LPS outer core biosynthesis locus which we have designated LPS genotype L4. Comparative bioinformatic analysis revealed that although the serovar 16 type strain contained a different LPS locus, L8, there was a significant degree of nucleotide identity between the L4 and L8 loci. Structural analysis revealed that the LPS glycoforms produced by the L4 and L8 strains all contained the highly conserved inner core produced by all other P. multocida strains examined to date. The residues within the LPS outer core produced by the L4 and L8 strains were either Gal or derivatives of Gal; unlike all other P. multocida Heddleston type strains examined there are no heptosyltransferases encoded in the L4 and L8 outer core biosynthesis loci. The structure of the L4 LPS outer core produced by the serovar 6 type strain consisted of β-Gal-(1-3)-β-N-acetylgalactosamine (GalNAc)-(1-4)-β-GalNAc3OAc-(1-4)-α-GalNAc3OAc-(1-3)-β-Gal, whereas the serovar 7 type strain produced a highly truncated LPS outer core containing only a single β-Gal residue. The structure of the L8 LPS outer core produced by the serovar 16 type strain consisted of β-Gal-(1-3)-β-GalNAc-(1-4)-(α-GalNAc-(1-3)-)-α-GalNAc.

LPS, structure, genetics, core oligosaccharide, Pasteurella multocida

Structure type: oligomer
Location inside paper: p.300, fig.3, serovar 16 strain P2723, Supplementary table SIII
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130648,IEDB_130650,IEDB_136044,IEDB_137472,IEDB_137473,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_1391961,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141582,IEDB_141584,IEDB_141794,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_152213,IEDB_153205,IEDB_153206,IEDB_156996,IEDB_190606,IEDB_2189047,IEDB_221845,IEDB_885822,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88

Methods: 13C NMR, 1H NMR, methylation, GLC-MS, PCR, DNA sequencing, de-O-acylation, sugar analysis, 31P NMR, GLC, MS/MS, CE-ESI-MS, bioinformatic analysis
Biosynthesis and genetic data: genetic data

Related record ID(s): 30607, 30757, 30759, 30904
NCBI Taxonomy refs (TaxIDs): 747
Reference(s) to other database(s): GTC:G98300XM
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	102.9	71.7	71.9	67.6	72.7	70.5	64.5
5,3,3,0	%xXEtN	63.1	41.3
5,3,3	P
5,3	aXLDmanHepp	100.7	79.3	76.3	66.2	73.3	70.5	64.5
5,4,4,3,3,2	Ac	?	23.4
5,4,4,3,3	aDGalpN	94.5	50.7	69.6	69.7	72.6	62.6
5,4,4,3,2	Ac	?	23.4
5,4,4,3,4,4	bDGalp	105.6	72.7	74.0	69.9	76.1	62.2
5,4,4,3,4	bDGalp	104.5	72.7	74.2	78.2	75.7	61.9
5,4,4,3	aDGalpN	95.3	49.3	72.5	72.3	71.9	61.9
5,4,4	bDGalp	104.0	70.9	77.7	65.8	76.0	62.2
5,4	bDGlcp	103.8	74.4	76.1	79.2	76.1	60.5
5,6	aDGlcp	102.7	73.3	74.2	69.9	72.7	60.9
5	aXLDmanHepp	97.6	71.6	74.9	75.1	72.7	80.3	63.2
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	5.11	3.97	3.90	3.81	3.81	4.04	3.75-3.75
5,3,3,0	%xXEtN	4.19	3.31
5,3,3	P
5,3	aXLDmanHepp	5.62	4.56	4.36	4.03	3.63	4.04	3.75-3.75
5,4,4,3,3,2	Ac	-	2.08
5,4,4,3,3	aDGalpN	5.22	4.34	3.69	4.03	3.89	3.79-3.79
5,4,4,3,2	Ac	-	2.08
5,4,4,3,4,4	bDGalp	4.61	3.62	3.68	3.92	3.70	3.78-3.78
5,4,4,3,4	bDGalp	4.43	3.73	3.71	4.19	3.63	3.81-3.81
5,4,4,3	aDGalpN	5.13	4.62	4.20	4.55	4.25	3.75-3.84
5,4,4	bDGalp	4.58	3.62	3.82	4.18	3.71	3.78-3.78
5,4	bDGlcp	4.71	3.51	3.62	3.75	3.68	3.95-4.01
5,6	aDGlcp	5.21	3.59	3.82	3.56	3.92	3.82-3.93
5	aXLDmanHepp	5.03	4.00	3.91	4.22	3.64	4.20	3.70-3.88
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	102.9/5.11	71.7/3.97	71.9/3.90	67.6/3.81	72.7/3.81	70.5/4.04	64.5/3.75-3.75
5,3,3,0	%xXEtN	63.1/4.19	41.3/3.31
5,3,3	P
5,3	aXLDmanHepp	100.7/5.62	79.3/4.56	76.3/4.36	66.2/4.03	73.3/3.63	70.5/4.04	64.5/3.75-3.75
5,4,4,3,3,2	Ac		23.4/2.08
5,4,4,3,3	aDGalpN	94.5/5.22	50.7/4.34	69.6/3.69	69.7/4.03	72.6/3.89	62.6/3.79-3.79
5,4,4,3,2	Ac		23.4/2.08
5,4,4,3,4,4	bDGalp	105.6/4.61	72.7/3.62	74.0/3.68	69.9/3.92	76.1/3.70	62.2/3.78-3.78
5,4,4,3,4	bDGalp	104.5/4.43	72.7/3.73	74.2/3.71	78.2/4.19	75.7/3.63	61.9/3.81-3.81
5,4,4,3	aDGalpN	95.3/5.13	49.3/4.62	72.5/4.20	72.3/4.55	71.9/4.25	61.9/3.75-3.84
5,4,4	bDGalp	104.0/4.58	70.9/3.62	77.7/3.82	65.8/4.18	76.0/3.71	62.2/3.78-3.78
5,4	bDGlcp	103.8/4.71	74.4/3.51	76.1/3.62	79.2/3.75	76.1/3.68	60.5/3.95-4.01
5,6	aDGlcp	102.7/5.21	73.3/3.59	74.2/3.82	69.9/3.56	72.7/3.92	60.9/3.82-3.93
5	aXLDmanHepp	97.6/5.03	71.6/4.00	74.9/3.91	75.1/4.22	72.7/3.64	80.3/4.20	63.2/3.70-3.88
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	5.11	3.97	3.90	3.81	3.81	4.04	3.75 3.75
5,3,3,0	%xXEtN	4.19	3.31
5,3,3	P
5,3	aXLDmanHepp	5.62	4.56	4.36	4.03	3.63	4.04	3.75 3.75
5,4,4,3,3,2	Ac		2.08
5,4,4,3,3	aDGalpN	5.22	4.34	3.69	4.03	3.89	3.79 3.79
5,4,4,3,2	Ac		2.08
5,4,4,3,4,4	bDGalp	4.61	3.62	3.68	3.92	3.70	3.78 3.78
5,4,4,3,4	bDGalp	4.43	3.73	3.71	4.19	3.63	3.81 3.81
5,4,4,3	aDGalpN	5.13	4.62	4.20	4.55	4.25	3.75 3.84
5,4,4	bDGalp	4.58	3.62	3.82	4.18	3.71	3.78 3.78
5,4	bDGlcp	4.71	3.51	3.62	3.75	3.68	3.95 4.01
5,6	aDGlcp	5.21	3.59	3.82	3.56	3.92	3.82 3.93
5	aXLDmanHepp	5.03	4.00	3.91	4.22	3.64	4.20	3.70 3.88
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	102.9	71.7	71.9	67.6	72.7	70.5	64.5
5,3,3,0	%xXEtN	63.1	41.3
5,3,3	P
5,3	aXLDmanHepp	100.7	79.3	76.3	66.2	73.3	70.5	64.5
5,4,4,3,3,2	Ac	?	23.4
5,4,4,3,3	aDGalpN	94.5	50.7	69.6	69.7	72.6	62.6
5,4,4,3,2	Ac	?	23.4
5,4,4,3,4,4	bDGalp	105.6	72.7	74.0	69.9	76.1	62.2
5,4,4,3,4	bDGalp	104.5	72.7	74.2	78.2	75.7	61.9
5,4,4,3	aDGalpN	95.3	49.3	72.5	72.3	71.9	61.9
5,4,4	bDGalp	104.0	70.9	77.7	65.8	76.0	62.2
5,4	bDGlcp	103.8	74.4	76.1	79.2	76.1	60.5
5,6	aDGlcp	102.7	73.3	74.2	69.9	72.7	60.9
5	aXLDmanHepp	97.6	71.6	74.9	75.1	72.7	80.3	63.2
4,0,0	xXEtN
4,0	%xXP?
4	P
	aXKdop

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](NC(C)=O)[C@@H](O[C@H]3[C@@H](O)[C@@H](CO)O[C@@H](O[C@@H]4[C@@H](CO)O[C@@H](O[C@@H]5[C@@H]([C@H](CO)O[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)O[C@H](O[C@@H]6[C@H](OP(=O)(O)OP(=O)(O)OCCN)C[C@](O)(C(=O)O)O[C@@H]6[C@H](O)CO)[C@@H](O)[C@H]5O[C@H]5O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](OP(=O)(O)OCCN)[C@@H]5O[C@H]5O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]5O)[C@H](O)[C@H]4O)[C@@H]3O)O[C@H](CO)[C@@H]2O[C@@H]2O[C@H](CO)[C@H](O[C@@H]3O[C@H](CO)[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

SVG MW SMILES 3D mol Ionize