Taxonomic group: bacteria / Proteobacteria (Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: infection due to Escherichia coli [ICD11: XN6P4 ]
 
The structure was elucidated in this paper
NCBI PubMed ID: 25898391
Publication DOI: 10.1016/j.carres.2015.03.014
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: perepelioc.ac.ru (A. V. Perepelov)
Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, TEDA School of Biological Sciences and Biotechnology, Nankai University, TEDA, Tianjin, China, Department of Laboratory Medicine, Division of Clinical Microbiology, Karolinska Institute, Karolinska University Hospital, Stockholm, Sweden

The O-polysaccharides (O-antigens) were isolated by mild acid degradation of the lipopolysaccharide (LPS) of Escherichia coli O46 and O134. The structures of their linear tetrasaccharide repeating units were established by sugar analysis along with 1D and 2D (1)H and (13)C NMR spectroscopy: [Formula: see text], where D-aThr indicates D-allothreonine and R indicates O-acetyl substitution (~ 70% on aThr and ~ 15% on GalNAc) in E. coli O46 whereas the O-acetylation is absent in E. coli O134. Functions of genes in the essentially identical O-antigen gene clusters of E. coli O46 and O134 were tentatively assigned by a comparison with sequences in available databases and found to be in agreement with the O-polysaccharide structures established.

O-antigen, Escherichia coli, O-polysaccharide, bacterial polysaccharide structure, O-antigen gene cluster, threonine

Structure type: polymer chemical repeating unit
Location inside paper: abstract, p.21, table 1, p.22, chart 1, E. coli O46, E. coli O134
The structure in this paper was incorrect:

← originally published structure   Show legend

Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_115136,IEDB_130648,IEDB_136044,IEDB_137472,IEDB_137473,IEDB_140630,IEDB_141794,IEDB_142488,IEDB_146664,IEDB_190606,IEDB_423153,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
 
Methods: 13C NMR, 1H NMR, NMR-2D, PCR, sugar analysis, DNA techniques, GLC, mild acid hydrolysis, de-O-acetylation, NMR-1D, GPC, function analysis of gene clusters
Biosynthesis and genetic data: genetic data
Comments, role: NMR data for O-deacetylated OPS E. coli O46. The OPS of E. coli O134 differs from the OPS of E. coli O46 only in the lack of O-acetylation. Title, abstract, and structure were corrcted according to Corrigendum in Carb. Res. 436 (2016) 54 : The authors regret about a mistake in the structures of the O-antigens of Escherichia coli O46 and O134. The amino acid present in these O-antigens is L-threonine, and not D-allothreonine as reported in the original version of the manuscript.
 
Related record ID(s): 30841
NCBI Taxonomy refs (TaxIDs): 562
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NMR conditions: in D2O at 303 K       [as TSV]

1H NMR data: Linkage Residue H1 H2 H3 H4 H5 H6 3,6,6,6 xLThr 4.45 4.41 1.25   3,6,6 bDGlcpA 4.60 3.40 3.67 3.97 4.11 3,6 bDGalp 4.37 3.53 3.62 3.92 3.86 3.93 4.00 3 bDGlcp 4.51 3.28 3.46 3.45 3.58 3.78 4.20 2 Ac 2.00     bDGalpN 4.49 4.00 3.85 4.17 3.65 3.75 3.82

13C NMR data: Linkage Residue C1 C2 C3 C4 C5 C6 3,6,6,6      xLThr 175.2 60.2 68.4 20.3   3,6,6      bDGlcpA 104.3 73.6 74.9 78.3 75.0 171.7 3,6      bDGalp 104.7 71.8 73.8 69.8 75.0 70.8 3      bDGlcp 105.4 74.1 76.7 70.7 75.8 70.0 2      Ac 176.0 23.6          bDGalpN 100.9 52.4 81.4 69.0 76.1 62.2

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