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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: respiratory infections [ICD11: CA45

]; infection due to Bordetella bronchiseptica [ICD11: XN173

]

The structure was elucidated in this paper
NCBI PubMed ID: 33494150
Publication DOI: 10.3390/ijms22031029
Journal NLM ID: 101092791
Publisher: Basel, Switzerland: MDPI
Correspondence: tomasz.niedziela

hirszfeld.pl
Institutions: Hirszfeld Institute of Immunology and Experimental Therapy, 53-114 Wroclaw, Poland

Bacterial pathogens expose on the cell surface a variety of complex carbohydrate molecules. Gram-negative bacteria produce lipopolysaccharides, which are the main components of the outer membrane of bacterial envelopes and play a major role in host-pathogen interactions. B. pertussis, B. parapertussis, B. bronchiseptica, and B. holmesii, are mammalian respiratory pathogens, having substantial economic impact on human health and agriculture. B. pertussis is responsible for whooping cough (pertussis) and B. holmesii is the second pertussis etiological factor, but the current anti-pertussis vaccines do not provide cross-protection. The structural data on any given hypothetical carbohydrate antigen is a prerequisite for further analysis of structure-related activities and their interaction with hosts. 1H NMR spectra constitute fingerprints of the analyzed glycans and provide unique identity information. The concept of structure-reporter groups has now been augmented by 1H,13C-correlation spectra of the Bordetella oligosaccharides. The comparative analysis of Bordetellae oligosaccharides (OS) revealed that the hexasaccharide, comprising the α-GlcpN, α-GlcpA, 4,6-disubstituted-β-Glcp, 2,7-disubstituted-l-α-d-Hepp, 3,4-disubstituted-l-α-d-Hepp, and Kdo, constitute the least variable OS segment. This minimal common element in the structure of lipopolysaccharides of Bordetellae could be used to devise a universal cross-protective vaccine component against infections with various bacteria from the genus Bordetella.

Lipopolysaccharide, core oligosaccharide, NMR spectroscopy, pertussis, Whooping Cough, Bordetella spp.

Structure type: oligomer
Location inside paper: Fig. 6, Fig. S5, Fig. S6, table 1
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115136,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140630,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_2189047,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, gel filtration, NMR-2D, SDS-PAGE, 31P NMR, HPLC, SEC
Comments, role: Published chemical shift of ?X4,7anhKdo? C1 (203.7) can be erroneous.

Related record ID(s): 10964, 10967
NCBI Taxonomy refs (TaxIDs): 518
Show glycosyltransferases

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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
5,3,2	aDGlcpA	100.8-101.9	71.8-72.9	72.1-72.9	72.1-73.0	73.1-74.1	175.3-176.6
5,3,4	P
5,3,7	aDGlcpN	96.8	55.1	70.9	70.3	73.3	61.1
5,3	aXLDmanHepp	100.8	80.3	71.3	72.1	72.8	68.8	70.7
5,4,4	%aDGlcpN	96.2	55.1	70.8	70.3	73.1	61.1
5,4,6	aDGalpNA	95.5	51.3	67.4	70.4	72.8	175.1
5,4	bDGlcp	102.9	74.3	77.1	78.5	72.7	68.1
5	aXLDmanHepp	98.7	74.2	79.9	73.4	72.3	69.4	63.6
	?X4,7anhKdo?	?	?	39.9-43.7	76.6-78.3	81.0-84.7	75.6-76.4	84.6-85.6	62.0-62.7


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
5,3,2	aDGlcpA	5.04-5.07	3.59	3.77-3.78	3.49	4.17-4.18	-
5,3,4	P
5,3,7	aDGlcpN	5.20	3.32	3.92	3.51	3.82	3.80-3.86
5,3	aXLDmanHepp	5.45	4.05	4.02	4.43	3.62	4.29	3.80
5,4,4	%aDGlcpN	5.22-5.23	3.38	3.92-3.94	3.49-3.50	3.74-3.77	3.76-3.84
5,4,6	aDGalpNA	5.26	3.55	4.13	4.27	4.48	-
5,4	bDGlcp	4.47	3.35	3.58	3.54	3.60	3.88-3.95
5	aXLDmanHepp	5.15	3.98	4.03	4.25	3.65	4.06	3.75
	?X4,7anhKdo?	-	-	3.18-3.19	4.55-4.59	4.17-4.20	4.16-4.18	3.82-3.87	3.67-3.74


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	aDGlcpA	100.8-101.9/5.04-5.07	71.8-72.9/3.59	72.1-72.9/3.77-3.78	72.1-73.0/3.49	73.1-74.1/4.17-4.18	
5,3,4	P
5,3,7	aDGlcpN	96.8/5.20	55.1/3.32	70.9/3.92	70.3/3.51	73.3/3.82	61.1/3.80-3.86
5,3	aXLDmanHepp	100.8/5.45	80.3/4.05	71.3/4.02	72.1/4.43	72.8/3.62	68.8/4.29	70.7/3.80
5,4,4	%aDGlcpN	96.2/5.22-5.23	55.1/3.38	70.8/3.92-3.94	70.3/3.49-3.50	73.1/3.74-3.77	61.1/3.76-3.84
5,4,6	aDGalpNA	95.5/5.26	51.3/3.55	67.4/4.13	70.4/4.27	72.8/4.48	
5,4	bDGlcp	102.9/4.47	74.3/3.35	77.1/3.58	78.5/3.54	72.7/3.60	68.1/3.88-3.95
5	aXLDmanHepp	98.7/5.15	74.2/3.98	79.9/4.03	73.4/4.25	72.3/3.65	69.4/4.06	63.6/3.75
	?X4,7anhKdo?			39.9-43.7/3.18-3.19	76.6-78.3/4.55-4.59	81.0-84.7/4.17-4.20	75.6-76.4/4.16-4.18	84.6-85.6/3.82-3.87	62.0-62.7/3.67-3.74

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
5,3,2	aDGlcpA	5.04 5.07	3.59	3.77 3.78	3.49	4.17 4.18
5,3,4	P
5,3,7	aDGlcpN	5.20	3.32	3.92	3.51	3.82	3.80 3.86
5,3	aXLDmanHepp	5.45	4.05	4.02	4.43	3.62	4.29	3.80
5,4,4	%aDGlcpN	5.22 5.23	3.38	3.92 3.94	3.49 3.50	3.74 3.77	3.76 3.84
5,4,6	aDGalpNA	5.26	3.55	4.13	4.27	4.48
5,4	bDGlcp	4.47	3.35	3.58	3.54	3.60	3.88 3.95
5	aXLDmanHepp	5.15	3.98	4.03	4.25	3.65	4.06	3.75
	?X4,7anhKdo?			3.18 3.19	4.55 4.59	4.17 4.20	4.16 4.18	3.82 3.87	3.67 3.74

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
5,3,2	aDGlcpA	100.8 101.9	71.8 72.9	72.1 72.9	72.1 73.0	73.1 74.1	175.3 176.6
5,3,4	P
5,3,7	aDGlcpN	96.8	55.1	70.9	70.3	73.3	61.1
5,3	aXLDmanHepp	100.8	80.3	71.3	72.1	72.8	68.8	70.7
5,4,4	%aDGlcpN	96.2	55.1	70.8	70.3	73.1	61.1
5,4,6	aDGalpNA	95.5	51.3	67.4	70.4	72.8	175.1
5,4	bDGlcp	102.9	74.3	77.1	78.5	72.7	68.1
5	aXLDmanHepp	98.7	74.2	79.9	73.4	72.3	69.4	63.6
	?X4,7anhKdo?	?	?	39.9 43.7	76.6 78.3	81.0 84.7	75.6 76.4	84.6 85.6	62.0 62.7

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

There are 2 chemically distinct structures. Please, select:

N[C@H]1[C@@H](OC[C@H](O)[C@H]2O[C@H](O[C@@H]3[C@H](O)[C@@H](O[C@@H]4[C@H]5CC(O)(C(=O)O)O[C@@H]4[C@@H](CO)O5)O[C@H]([C@@H](O)CO)[C@H]3O[C@@H]3O[C@H](CO[C@H]4O[C@H](C(=O)O)[C@H](O)[C@H](O)[C@H]4N)[C@@H](O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4N)[C@H](O)[C@H]3O)[C@@H](O[C@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@@H]2OP(=O)(O)O)O[C@H](CO)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize