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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: gastroenteritis [ICD11: 1A40.0

]; infection due to Vibrio parahaemolyticus [ICD11: XN1AA

]

The structure was elucidated in this paper
NCBI PubMed ID: 7392309
Publication DOI: 10.1016/j.carres.2016.06.004
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: goran.widmalm

su.se
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, International Centre for Diarrhoeal Disease Research, Dhaka, Bangladesh, Karolinska Institute, Department of Laboratory Medicine, Division of Clinical Microbiology, Karolinska University Hospital, Stockholm, Sweden

The structure of a polysaccharide from Vibrio parahaemolyticus strain AN-16000 has been investigated. The sugar and absolute configuration analysis revealed d-Glc, d-GalN, d-QuiN and l-FucN as major components. The PS was subjected to dephosphorylation with aqueous 40% HF to obtain an oligosaccharide that was analyzed by (1)H and (13)C NMR spectroscopy. The HR-MS spectrum of the oligosaccharide revealed a pentasaccharide composed of two Glc residues, one QuiNAc and one GalNAc, one FucNAc, as well as a glycerol moiety. The structure of the PS was determined using (1)H, (13)C, (15)N and (31)P NMR spectroscopy; inter-residue correlations were identified by (1)H,(13)C-heteronuclear multiple-bond correlation, (1)H,(1)H-NOESY and (1)H,(31)P-hetero-TOCSY experiments. The PS backbone has the following teichoic acid-like structure: →3)-d-Gro-(1-P-6)-β-d-Glcp-(1→4)-α-l-FucpNAc-(1→3)-β-d-QuipNAc-(1 → with a side-chain consisting of α-d-Glcp-(1→6)-α-d-GalpNAc-(1→ linked to the O3 position of the FucNAc residue.

NMR, Vibrio parahaemolyticus, dephosphorylation, Glycerol-1-phosphate

Structure type: oligomer
Location inside paper: p.43, table 1
Compound class: CPS
Contained glycoepitopes: IEDB_130648,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_885822,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, NMR-2D, HF solvolysis, sugar analysis, ESI-MS, acid hydrolysis, GLC, NMR-1D, GPC, mild acid degradation
Comments, role: dephosphorylation of the PS

Related record ID(s): 11800, 11801, 11802, 11803, 11804, 11805
NCBI Taxonomy refs (TaxIDs): 670
Reference(s) to other database(s): GTC:G85509KP
Show glycosyltransferases

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

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
1,3,3,6	aDGlcp	97.38	71.82	74.49-74.52	70.26	72.35	61.34
1,3,3,2	Ac	174.78	23.05
1,3,3	aDGalpN	98.30	50.42	68.71	69.54	70.46	66.01
1,3,2	Ac	174.19	22.93
1,3,4	bDGlcp	103.82	74.49-74.52	76.40	70.40	77.06	61.67
1,3	aLFucpN	98.36	50.05	70.40	78.19	68.47	16.11
1,2	Ac	174.66	22.74
1	bDQuipN	102.44	56.61	78.65	74.49-74.52	72.61	17.47
	xSGro	71.66	71.23	63.23


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
1,3,3,6	aDGlcp	4.934	3.590	3.530	3.477	3.847	3.766-3.897
1,3,3,2	Ac	-	2.022
1,3,3	aDGalpN	5.073	4.149	3.921	4.021	4.342	3.553-3.933
1,3,2	Ac	-	1.940
1,3,4	bDGlcp	4.643	3.463	3.532	3.434	3.436	3.670-3.882
1,3	aLFucpN	4.998	4.362	4.050	4.269	4.532	1.329
1,2	Ac	-	1.954
1	bDQuipN	4.426	3.853	3.362	3.466	3.517	1.335
	xSGro	3.568-3.890	3.809	3.516-3.591


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
1,3,3,6	aDGlcp	97.38/4.934	71.82/3.590	74.49-74.52/3.530	70.26/3.477	72.35/3.847	61.34/3.766-3.897
1,3,3,2	Ac		23.05/2.022
1,3,3	aDGalpN	98.30/5.073	50.42/4.149	68.71/3.921	69.54/4.021	70.46/4.342	66.01/3.553-3.933
1,3,2	Ac		22.93/1.940
1,3,4	bDGlcp	103.82/4.643	74.49-74.52/3.463	76.40/3.532	70.40/3.434	77.06/3.436	61.67/3.670-3.882
1,3	aLFucpN	98.36/4.998	50.05/4.362	70.40/4.050	78.19/4.269	68.47/4.532	16.11/1.329
1,2	Ac		22.74/1.954
1	bDQuipN	102.44/4.426	56.61/3.853	78.65/3.362	74.49-74.52/3.466	72.61/3.517	17.47/1.335
	xSGro	71.66/3.568-3.890	71.23/3.809	63.23/3.516-3.591

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
1,3,3,6	aDGlcp	4.934	3.590	3.530	3.477	3.847	3.766 3.897
1,3,3,2	Ac		2.022
1,3,3	aDGalpN	5.073	4.149	3.921	4.021	4.342	3.553 3.933
1,3,2	Ac		1.940
1,3,4	bDGlcp	4.643	3.463	3.532	3.434	3.436	3.670 3.882
1,3	aLFucpN	4.998	4.362	4.050	4.269	4.532	1.329
1,2	Ac		1.954
1	bDQuipN	4.426	3.853	3.362	3.466	3.517	1.335
	xSGro	3.568 3.890	3.809	3.516 3.591

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
1,3,3,6	aDGlcp	97.38	71.82	74.49 74.52	70.26	72.35	61.34
1,3,3,2	Ac	174.78	23.05
1,3,3	aDGalpN	98.30	50.42	68.71	69.54	70.46	66.01
1,3,2	Ac	174.19	22.93
1,3,4	bDGlcp	103.82	74.49 74.52	76.40	70.40	77.06	61.67
1,3	aLFucpN	98.36	50.05	70.40	78.19	68.47	16.11
1,2	Ac	174.66	22.74
1	bDQuipN	102.44	56.61	78.65	74.49 74.52	72.61	17.47
	xSGro	71.66	71.23	63.23

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](OC[C@@H](O)CO)[C@@H]2NC(C)=O)O[C@@H](C)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]1O[C@H]1O[C@H](CO[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1NC(C)=O

SVG MW SMILES 3D mol Ionize