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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: acute otitis media [ICD11: AB00

, Life stage: adult]; chronic respiratory tract infections [ICD11: CA45

, ICD11: CB7Z

]; infection due to Haemophilus influenzae [ICD11: XN1P6

]

The structure was elucidated in this paper
NCBI PubMed ID: 23582099
Publication DOI: 10.1016/j.carres.2013.03.011
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: E.K.H. Schweda <elksc

ifm.liu.se>
Institutions: Clinical Research Centre, Karolinska Institutet, Novum, S-141 86 Huddinge, Sweden

We report the novel branching pattern in lipopolysaccharide (LPS) expressed by non-typeable Haemophilus influenzae (NTHi) strain 1232. The strain expressed the β-D-Glcp-(1→4)-[α-D-Galp-(1→4)-β-D-Galp-(1→7)]-D-α-D-Hepp-(1→6)-β-D-Glcp chain linked to the proximal heptose (HepI) of the conserved triheptosyl inner-core moiety of NTHi LPS: L-α-D-HepIIIp-(1→2)-[PEtn→6]-L-α-D-HepIIp-(1→3)-L-α-D-HepIp-(1→5)-[PPEtn→4]-α-Kdop-(2→6)-lipid A. The structure has been elucidated using NMR spectroscopy, electrospray ionization mass spectrometry (ESI-MS) and capillary electrophoresis coupled to electrospray ionization tandem mass spectrometry (CE-ESI-MS(n)) on O-deacylated LPS and core oligosaccharide (OS) materials, as well as HPLC-ESI-MS(n) on permethylated, dephosphorylated OS. It was also found that a tetrasaccharide unit bearing sialic acid [α-Neu5Ac-(2→3)-β-D-Galp-(1→4)-β-D-GlcNAcp-(1→3)-β-D-Galp-(1→] could substitute O-4 of the β-D-Glcp linked to HepI. In addition, the distal heptose (HepIII) was substituted by PCho→6-β-D-Galp-(1→ at the O-2 position.

Lipopolysaccharide, Haemophilus influenzae, NMR spectroscopy, D-glycero-D-manno-heptose, losA1, Sialyllacto-N-neotetraose

Structure type: oligomer
Location inside paper: p.121, fig.5
Aglycon: lipid A
Compound class: LPS
Contained glycoepitopes: IEDB_115009,IEDB_116046,IEDB_120354,IEDB_123890,IEDB_130646,IEDB_130650,IEDB_130651,IEDB_130697,IEDB_135813,IEDB_136044,IEDB_136794,IEDB_136906,IEDB_137340,IEDB_137472,IEDB_137776,IEDB_137777,IEDB_137779,IEDB_138949,IEDB_1391966,IEDB_139428,IEDB_140087,IEDB_140088,IEDB_140090,IEDB_140108,IEDB_140110,IEDB_140122,IEDB_140624,IEDB_141794,IEDB_141807,IEDB_142351,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_146100,IEDB_146664,IEDB_148488,IEDB_149144,IEDB_149174,IEDB_150933,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_423120,IEDB_742247,IEDB_983931,SB_115,SB_116,SB_131,SB_145,SB_165,SB_166,SB_170,SB_171,SB_172,SB_173,SB_187,SB_192,SB_195,SB_30,SB_31,SB_39,SB_6,SB_62,SB_68,SB_7,SB_84,SB_88

Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, HF solvolysis, de-O-acylation, sugar analysis, ESI-MS, mild acid hydrolysis, HPLC, CE-ESI-MS
Comments, role: O-deacylated OS from H. influenzae NTHi 1232

Related record ID(s): 29379
NCBI Taxonomy refs (TaxIDs): 727
Show glycosyltransferases

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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7
5,3,2,2,6,0	xXCho	59.9	66.1	?
5,3,2,2,6	P
5,3,2,2	bDGalp	103.7	70.5	72.3	68.8	?	?
5,3,2	aXLDmanHepp	100.00	79.3	70.5	?	?	?	?
5,3,6,0	xXEtN	62.1	40.1
5,3,6	P
5,3	aXLDmanHepp	99.03	79.3	69.0	?	?	74.9	61.3
5,4,4,3,4,3,5	Ac
5,4,4,3,4,3	aXNeup
5,4,4,3,4	bDGalp
5,4,4,3,2	Ac
5,4,4,3	bDGlcpN
5,4,4	bDGalp
5,4,6,4	bDGlcp	103.3	73.5	75.6	69.9	76.5	61.0
5,4,6,7,4	aDGalp	100.6	68.6	70.4	70.7	70.9	?
5,4,6,7	bDGalp	103.6	71.2	72.4	77.3	?	?
5,4,6	aXDDmanHepp	99.3	69.5	?	78.1	?	69.1	70.1
5,4	bDGlcp	103.7	73.7	76.8	70.2	73.7	65.7
5	aXLDmanHepp	97.0	70.5	72.4	73.5	?	68.0	?
4,0,0	xXEtN
4,0	P
4	P
	aXKdop


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7
5,3,2,2,6,0	xXCho	4.35	3.70	?
5,3,2,2,6	P
5,3,2,2	bDGalp	4.38	3.58	3.70	3.91	?	?
5,3,2	aXLDmanHepp	4.97	4.13	3.99	?	?	?	?
5,3,6,0	xXEtN	4.14	3.29
5,3,6	P
5,3	aXLDmanHepp	5.67	4.18	3.93	?	3.71	4.56	3.88
5,4,4,3,4,3,5	Ac
5,4,4,3,4,3	aXNeup
5,4,4,3,4	bDGalp
5,4,4,3,2	Ac
5,4,4,3	bDGlcpN
5,4,4	bDGalp
5,4,6,4	bDGlcp	4.57	3.29	3.54	3.39	3.54	3.72-3.95
5,4,6,7,4	aDGalp	4.97	3.83	3.93	4.04	4.38	?
5,4,6,7	bDGalp	4.53	3.61	3.75	4.05	?	?
5,4,6	aXDDmanHepp	4.97	4.10	?	3.96	?	4.36	3.81-4.28
5,4	bDGlcp	4.49	3.40	3.44	3.53	3.58	3.84-4.00
5	aXLDmanHepp	5.05	3.98	3.99	4.26	?	4.10	?
4,0,0	xXEtN
4,0	P
4	P
	aXKdop


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7
5,3,2,2,6,0	xXCho	59.9/4.35	66.1/3.70	?/?
5,3,2,2,6	P
5,3,2,2	bDGalp	103.7/4.38	70.5/3.58	72.3/3.70	68.8/3.91	?/?	?/?
5,3,2	aXLDmanHepp	100.00/4.97	79.3/4.13	70.5/3.99	?/?	?/?	?/?	?/?
5,3,6,0	xXEtN	62.1/4.14	40.1/3.29
5,3,6	P
5,3	aXLDmanHepp	99.03/5.67	79.3/4.18	69.0/3.93	?/?	?/3.71	74.9/4.56	61.3/3.88
5,4,4,3,4,3,5	Ac
5,4,4,3,4,3	aXNeup
5,4,4,3,4	bDGalp
5,4,4,3,2	Ac
5,4,4,3	bDGlcpN
5,4,4	bDGalp
5,4,6,4	bDGlcp	103.3/4.57	73.5/3.29	75.6/3.54	69.9/3.39	76.5/3.54	61.0/3.72-3.95
5,4,6,7,4	aDGalp	100.6/4.97	68.6/3.83	70.4/3.93	70.7/4.04	70.9/4.38	?/?
5,4,6,7	bDGalp	103.6/4.53	71.2/3.61	72.4/3.75	77.3/4.05	?/?	?/?
5,4,6	aXDDmanHepp	99.3/4.97	69.5/4.10	?/?	78.1/3.96	?/?	69.1/4.36	70.1/3.81-4.28
5,4	bDGlcp	103.7/4.49	73.7/3.40	76.8/3.44	70.2/3.53	73.7/3.58	65.7/3.84-4.00
5	aXLDmanHepp	97.0/5.05	70.5/3.98	72.4/3.99	73.5/4.26	?/?	68.0/4.10	?/?
4,0,0	xXEtN
4,0	P
4	P
	aXKdop

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6	H7
5,3,2,2,6,0	xXCho	4.35	3.70	?
5,3,2,2,6	P
5,3,2,2	bDGalp	4.38	3.58	3.70	3.91	?	?
5,3,2	aXLDmanHepp	4.97	4.13	3.99	?	?	?	?
5,3,6,0	xXEtN	4.14	3.29
5,3,6	P
5,3	aXLDmanHepp	5.67	4.18	3.93	?	3.71	4.56	3.88
5,4,4,3,4,3,5	Ac
5,4,4,3,4,3	aXNeup
5,4,4,3,4	bDGalp
5,4,4,3,2	Ac
5,4,4,3	bDGlcpN
5,4,4	bDGalp
5,4,6,4	bDGlcp	4.57	3.29	3.54	3.39	3.54	3.72 3.95
5,4,6,7,4	aDGalp	4.97	3.83	3.93	4.04	4.38	?
5,4,6,7	bDGalp	4.53	3.61	3.75	4.05	?	?
5,4,6	aXDDmanHepp	4.97	4.10	?	3.96	?	4.36	3.81 4.28
5,4	bDGlcp	4.49	3.40	3.44	3.53	3.58	3.84 4.00
5	aXLDmanHepp	5.05	3.98	3.99	4.26	?	4.10	?
4,0,0	xXEtN
4,0	P
4	P
	aXKdop

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6	C7
5,3,2,2,6,0	xXCho	59.9	66.1	?
5,3,2,2,6	P
5,3,2,2	bDGalp	103.7	70.5	72.3	68.8	?	?
5,3,2	aXLDmanHepp	100.00	79.3	70.5	?	?	?	?
5,3,6,0	xXEtN	62.1	40.1
5,3,6	P
5,3	aXLDmanHepp	99.03	79.3	69.0	?	?	74.9	61.3
5,4,4,3,4,3,5	Ac
5,4,4,3,4,3	aXNeup
5,4,4,3,4	bDGalp
5,4,4,3,2	Ac
5,4,4,3	bDGlcpN
5,4,4	bDGalp
5,4,6,4	bDGlcp	103.3	73.5	75.6	69.9	76.5	61.0
5,4,6,7,4	aDGalp	100.6	68.6	70.4	70.7	70.9	?
5,4,6,7	bDGalp	103.6	71.2	72.4	77.3	?	?
5,4,6	aXDDmanHepp	99.3	69.5	?	78.1	?	69.1	70.1
5,4	bDGlcp	103.7	73.7	76.8	70.2	73.7	65.7
5	aXLDmanHepp	97.0	70.5	72.4	73.5	?	68.0	?
4,0,0	xXEtN
4,0	P
4	P
	aXKdop

The spectrum also has 16 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](CO)O[C@@H](O[C@@H]3[C@@H](CO[C@H]4O[C@H]([C@H](O)CO[C@@H]5O[C@H](CO)[C@H](O[C@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6O)[C@H](O)[C@H]5O)[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@H](O)[C@@H]4O)O[C@@H](O[C@@H]4[C@@H]([C@@H](O)CO)O[C@H](O[C@@H]5[C@H](OP(=O)(O)OP(=O)(O)OCCN)C[C@](O)(C(=O)O)O[C@@H]5[C@H](O)CO)[C@@H](O)[C@H]4O[C@H]4O[C@H]([C@H](CO)OP(=O)(O)OCCN)[C@@H](O)[C@H](O)[C@@H]4O[C@H]4O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)[C@@H]4O[C@@H]4O[C@H](COP(=O)(O)OCC[N+](C)(C)C)[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@]3(C(=O)O)C[C@H](O)[C@@H](NC(C)=O)[C@H]([C@H](O)[C@H](O)CO)O3)[C@H]2O)[C@@H]1O

SVG MW SMILES 3D mol Ionize