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Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11: XN6P4

]

The structure was elucidated in this paper
NCBI PubMed ID: 10573858
Publication DOI: 10.1016/S0008-6215(99)00142-1
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: G. Widmalm <gw

organ.su.se>
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S- 106 91 Stockholm, Sweden, Karolinska Institute, Department of Immunology, Microbiology, Pathology and Infectious Diseases, Division of Clinical and Oral Bacteriology, Huddinge University Hospital, S- 141 86 Huddinge, Sweden

The structure of the O-antigen polysaccharide (PS) from Escherichia coli O173 has been investigated. Sugar and methylation analyses, electrospray ionisation mass spectrometry together with 1H, 31P and 13C NMR spectroscopy were the main methods used. The structure of the pentasaccharide repeating unit of the PS was found to be: [see structure in text]. By treatment with 48% HF the phosphoric diester linkage was cleaved together with the glycosidic linkage of the fucosyl group, rendering a tetrasaccharide with the structure: a-D-Glcp-(1→2)-b-D-Glcp-(1→3)-b-D-GlcpNAc-(1→3)-D-Glc.

structural, polysaccharide, O-antigen, O antigen, Escherichia, Escherichia coli, structural studies

Structure type: oligomer
Location inside paper: tetrasaccharide 1, Table 1
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_983931,SB_192

Methods: 13C NMR, 1H NMR, methylation, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, ESI-MS
Comments, role: tetrasaccharide 1 after HF hydrolysis of the OPS, α-anomer

Related record ID(s): 318, 3159
NCBI Taxonomy refs (TaxIDs): 562
Reference(s) to other database(s): GTC:G92734MB, GlycomeDB:25939
Show glycosyltransferases

NMR conditions: in D2O at 323 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,3,2	aDGlcp	98.6	72.8	74.1	70.8	?	?
3,3	bDGlcp	102.3	78.7	75.9	70.8	?	?
3,2	Ac	174.0	23.5
3	bDGlcpN	102.4	56.6	80.6	69.7	?	?
	aDGlcp	93.2	72.3	83.5	69.4	?	?


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,3,2	aDGlcp	5.29	3.50	3.72	3.42	?	?
3,3	bDGlcp	4.69	3.46	3.55	3.42	?	?
3,2	Ac	-	2.03
3	bDGlcpN	4.83-4.85	3.77-3.78	4.01	3.57	?	?
	aDGlcp	5.15	3.55	3.78	3.44	?	?


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,3,2	aDGlcp	98.6/5.29	72.8/3.50	74.1/3.72	70.8/3.42	?/?	?/?
3,3	bDGlcp	102.3/4.69	78.7/3.46	75.9/3.55	70.8/3.42	?/?	?/?
3,2	Ac		23.5/2.03
3	bDGlcpN	102.4/4.83-4.85	56.6/3.77-3.78	80.6/4.01	69.7/3.57	?/?	?/?
	aDGlcp	93.2/5.15	72.3/3.55	83.5/3.78	69.4/3.44	?/?	?/?

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,3,2	aDGlcp	5.29	3.50	3.72	3.42	?	?
3,3	bDGlcp	4.69	3.46	3.55	3.42	?	?
3,2	Ac		2.03
3	bDGlcpN	4.83 4.85	3.77 3.78	4.01	3.57	?	?
	aDGlcp	5.15	3.55	3.78	3.44	?	?

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,3,2	aDGlcp	98.6	72.8	74.1	70.8	?	?
3,3	bDGlcp	102.3	78.7	75.9	70.8	?	?
3,2	Ac	174.0	23.5
3	bDGlcpN	102.4	56.6	80.6	69.7	?	?
	aDGlcp	93.2	72.3	83.5	69.4	?	?

The spectrum also has 8 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](O)O[C@H](CO)[C@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize