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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: cystic fibrosis (CF) [ICD11: CA25

]

The structure was elucidated in this paper
NCBI PubMed ID: 18684854
Publication DOI: 10.1093/glycob/cwn074
Journal NLM ID: 9104124
Publisher: IRL Press at Oxford University Press
Correspondence: molinaro

unita.it
Institutions: Istituto per la Chimica e la Tecnologia dei Materiali Polimerici - ICTMP - CNR, Catania, Italy, Dipartimento di Chimica Organica e Biochimica, Università di Napoli Federico II, Napoli, Via Cintia, 4. I-80126 Italy, Centre for Veterinary Science, Department of Veterinary Medicine, University of Cambridge, Cambridge, UK, Department of Medical Microbiology and fCardiopulmonary Transplantation, Freeman Hospital, Newcastle, UK, Applied Immunobiology and Transplantation Group, Institute of Cellular Medicine, University of Newcastle, Newcastle, UK

The Burkholderia cepacia complex is a group of Gram negative bacteria that are opportunistic pathogens for humans especially in cystic fibrosis patients. Lipopolysaccharide molecules, are potent virulence factors of Gram negative bacteria organisms essential for bacterial survival. A complete analysis of the bacterial lipopolysaccharide structure to function relationship is required to understand the chemical basis of the inflammatory process. We have therefore investigated the structures of lipopolysaccharides from clonally identical Burkholderia multivorans strains (genomovar II) isolated pre- and post- lung transplantation through compositional analysis, mass spectrometry and 2D NMR spectroscopy. We tested the LPS' pro-inflammatory activity as a stimulant of human myelomonocytic U937 cell cytokine induction and assessed TLR4/MD2 signalling. Marked changes between the paired strains were found in the lipid A-inner core region. Such structural variations can contribute to the bacterial survival and persistence of infections despite the loss of a CF milieu following lung transplantation

Lipopolysaccharide, NMR spectroscopy, cystic fibrosis, virulence factor, Burkholderia cepacia complex, Burkholderia multivorans, lung transplantation

Structure type: oligomer
Location inside paper: p. 874, Fr1, suppl. table 2
Trivial name: alternative glycoform
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130648,IEDB_130650,IEDB_130670,IEDB_135607,IEDB_135609,IEDB_136105,IEDB_137473,IEDB_1391961,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_141582,IEDB_141584,IEDB_142488,IEDB_146664,IEDB_153207,IEDB_2189047,IEDB_225177,IEDB_226811,IEDB_885822,IEDB_885823,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, methylation, NMR-2D, SDS-PAGE, 31P NMR, MALDI-TOF MS, composition analysis, NMR-1D
Biological activity: biological activity data
Comments, role: published NMR assignment of #5_aLDmanHep C3 (70.5), terminal bDGlcp C3 (72.3) and C5 (68.4) are erroneous in supplementary table 2

Related record ID(s): 22657, 22980
NCBI Taxonomy refs (TaxIDs): 87883
Reference(s) to other database(s): GTC:G84677GR, GlycomeDB:36952
Show glycosyltransferases

NMR conditions: in D2O at 300 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
4	aXKop	?	?	70.8	68.8	70.2	72.3	70.4	63.7
5,3,2,3,2	Ac
5,3,2,3	%bDQuipN	102.33	55.9	75.5	75.0	75.5	16.9
5,3,2	aLRhap	97.85	69.9	80.3	70.5	70.8	17.2
5,3,3,3,3,3	bDGlcp	104.88	70.4	?	70.8	?	60.8
5,3,3,3,3,2	Ac
5,3,3,3,3	aDGalpN	93.4	47.9	77.1	73.2	71.5	63.1
5,3,3,3,2	Ac
5,3,3,3	%bDGalpN	102.4	50.9	74.38	71.9	75.01	60.8
5,3,3	aLRhap	97.2	70.6	79.9	70.9	70.0	16.6
5,3,7	aXLDmanHepp	101.27	69.9	70.3	70.5	71.6	69.9	62.9
5,3	aXLDmanHepp	99.02	71.2	69.8	69.2	70.4	66.4	70.73
5,4,6	aXLDmanHepp	97.31	70.0	70.1	71.5	71.8	68.6	62.8
5,4	bDGlcp	102.3	73.5	75.6	70.5	72.0	65.3
5	aXLDmanHepp	98.72	70.6	?	70.2	72.8	68.8	61.7
	aXKdo?	?	?	33.8	71.6	68.4	71.6	71.8	63.7


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
4	aXKop	-	-	3.74	3.87	3.95	3.54	3.92	3.59-3.83
5,3,2,3,2	Ac
5,3,2,3	%bDQuipN	4.57	3.59	3.66	3.05	3.35	1.18
5,3,2	aLRhap	4.68	3.84	3.73	3.28	3.73	1.17
5,3,3,3,3,3	bDGlcp	4.29	3.35	3.47	3.37	3.75	3.50-3.60
5,3,3,3,3,2	Ac
5,3,3,3,3	aDGalpN	4.92	4.23	3.71	4.11	3.97	3.45-3.63
5,3,3,3,2	Ac
5,3,3,3	%bDGalpN	4.60	3.95	3.66	3.99	3.51	3.58-3.67
5,3,3	aLRhap	4.81	3.75	3.77	3.38	3.82	1.13
5,3,7	aXLDmanHepp	4.78	3.82	3.71	3.71	3.51	3.83	3.52-3.59
5,3	aXLDmanHepp	5.12	4.19	3.83	3.85	3.79	3.79	3.56-3.62
5,4,6	aXLDmanHepp	4.80	3.84	3.94	3.89	3.56	3.86	3.52-3.58
5,4	bDGlcp	4.39	3.15	3.34	3.28	3.56	3.82-3.89
5	aXLDmanHepp	5.15	3.93	3.91	3.94	3.62	3.85	3.57-3.66
	aXKdo?	-	-	1.94-2.05	3.97	4.09	3.68	3.90	3.61-3.79


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8
4	aXKop			70.8/3.74	68.8/3.87	70.2/3.95	72.3/3.54	70.4/3.92	63.7/3.59-3.83
5,3,2,3,2	Ac
5,3,2,3	%bDQuipN	102.33/4.57	55.9/3.59	75.5/3.66	75.0/3.05	75.5/3.35	16.9/1.18
5,3,2	aLRhap	97.85/4.68	69.9/3.84	80.3/3.73	70.5/3.28	70.8/3.73	17.2/1.17
5,3,3,3,3,3	bDGlcp	104.88/4.29	70.4/3.35	?/3.47	70.8/3.37	?/3.75	60.8/3.50-3.60
5,3,3,3,3,2	Ac
5,3,3,3,3	aDGalpN	93.4/4.92	47.9/4.23	77.1/3.71	73.2/4.11	71.5/3.97	63.1/3.45-3.63
5,3,3,3,2	Ac
5,3,3,3	%bDGalpN	102.4/4.60	50.9/3.95	74.38/3.66	71.9/3.99	75.01/3.51	60.8/3.58-3.67
5,3,3	aLRhap	97.2/4.81	70.6/3.75	79.9/3.77	70.9/3.38	70.0/3.82	16.6/1.13
5,3,7	aXLDmanHepp	101.27/4.78	69.9/3.82	70.3/3.71	70.5/3.71	71.6/3.51	69.9/3.83	62.9/3.52-3.59
5,3	aXLDmanHepp	99.02/5.12	71.2/4.19	69.8/3.83	69.2/3.85	70.4/3.79	66.4/3.79	70.73/3.56-3.62
5,4,6	aXLDmanHepp	97.31/4.80	70.0/3.84	70.1/3.94	71.5/3.89	71.8/3.56	68.6/3.86	62.8/3.52-3.58
5,4	bDGlcp	102.3/4.39	73.5/3.15	75.6/3.34	70.5/3.28	72.0/3.56	65.3/3.82-3.89
5	aXLDmanHepp	98.72/5.15	70.6/3.93	?/3.91	70.2/3.94	72.8/3.62	68.8/3.85	61.7/3.57-3.66
	aXKdo?			33.8/1.94-2.05	71.6/3.97	68.4/4.09	71.6/3.68	71.8/3.90	63.7/3.61-3.79

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8
4	aXKop			3.74	3.87	3.95	3.54	3.92	3.59 3.83
5,3,2,3,2	Ac
5,3,2,3	%bDQuipN	4.57	3.59	3.66	3.05	3.35	1.18
5,3,2	aLRhap	4.68	3.84	3.73	3.28	3.73	1.17
5,3,3,3,3,3	bDGlcp	4.29	3.35	3.47	3.37	3.75	3.50 3.60
5,3,3,3,3,2	Ac
5,3,3,3,3	aDGalpN	4.92	4.23	3.71	4.11	3.97	3.45 3.63
5,3,3,3,2	Ac
5,3,3,3	%bDGalpN	4.60	3.95	3.66	3.99	3.51	3.58 3.67
5,3,3	aLRhap	4.81	3.75	3.77	3.38	3.82	1.13
5,3,7	aXLDmanHepp	4.78	3.82	3.71	3.71	3.51	3.83	3.52 3.59
5,3	aXLDmanHepp	5.12	4.19	3.83	3.85	3.79	3.79	3.56 3.62
5,4,6	aXLDmanHepp	4.80	3.84	3.94	3.89	3.56	3.86	3.52 3.58
5,4	bDGlcp	4.39	3.15	3.34	3.28	3.56	3.82 3.89
5	aXLDmanHepp	5.15	3.93	3.91	3.94	3.62	3.85	3.57 3.66
	aXKdo?			1.94 2.05	3.97	4.09	3.68	3.90	3.61 3.79

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8
4	aXKop	?	?	70.8	68.8	70.2	72.3	70.4	63.7
5,3,2,3,2	Ac
5,3,2,3	%bDQuipN	102.33	55.9	75.5	75.0	75.5	16.9
5,3,2	aLRhap	97.85	69.9	80.3	70.5	70.8	17.2
5,3,3,3,3,3	bDGlcp	104.88	70.4	?	70.8	?	60.8
5,3,3,3,3,2	Ac
5,3,3,3,3	aDGalpN	93.4	47.9	77.1	73.2	71.5	63.1
5,3,3,3,2	Ac
5,3,3,3	%bDGalpN	102.4	50.9	74.38	71.9	75.01	60.8
5,3,3	aLRhap	97.2	70.6	79.9	70.9	70.0	16.6
5,3,7	aXLDmanHepp	101.27	69.9	70.3	70.5	71.6	69.9	62.9
5,3	aXLDmanHepp	99.02	71.2	69.8	69.2	70.4	66.4	70.73
5,4,6	aXLDmanHepp	97.31	70.0	70.1	71.5	71.8	68.6	62.8
5,4	bDGlcp	102.3	73.5	75.6	70.5	72.0	65.3
5	aXLDmanHepp	98.72	70.6	?	70.2	72.8	68.8	61.7
	aXKdo?	?	?	33.8	71.6	68.4	71.6	71.8	63.7

The spectrum also has 7 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](O)[C@H](C)O[C@@H](O[C@H]3[C@@H](O[C@@H]4O[C@@H](C)[C@H](O)[C@@H](O[C@@H]5O[C@H](CO)[C@H](O)[C@H](O[C@H]6O[C@H](CO)[C@H](O)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H]6NC(C)=O)[C@H]5NC(C)=O)[C@H]4O)[C@H](O)[C@@H]([C@@H](O)CO[C@H]4O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]4O)O[C@@H]3O[C@@H]3[C@H](O)[C@@H](O[C@@H]4[C@H](O[C@@]5(C(=O)O)O[C@H]([C@H](O)CO)[C@H](O)[C@H](O)[C@@H]5O)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]4O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]4O)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]2O)O[C@H](C)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize