Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 7544238Publication DOI: 10.1016/0008-6215(95)00041-QJournal NLM ID: 0043535Publisher: Elsevier
Correspondence: torgov
ioc.ac.ru
Institutions: Max-Planck-Institut für Immunbiologie, Freiburg, Germany
Structures for the N-acetylneuraminic acid (Neu5Ac)-containing O56 and O24 polysaccharides of Escherichia coli have been reported previously. During these studies unusual chemical shifts had been observed for the NMR signals for H-3eq and C-3 of the Neu5Ac residues of both polysaccharides. In further pursuing this phenomenon, we have reinvestigated the O56 and O24 polysaccharides as well as derived oligosaccharides by one- and two-dimensional NMR spectroscopy. The results showed that structures of both polysaccharides (PSs) had to be modified and formulated as [formula: see text] 2D ROESY spectra revealed a strong NOE between H-3eq of Neu5Ac and the protons of the side-chain sugar (H-3 and H-5 of α-D-Galp in the O56 PS and H-3 of α-D-Glcp in the O24 PS) and also between H-3ax of Neu5Ac and H-3 of β-D-Glcp in the main chain. This indicated a close spatial association of the seven-linked α-Neu5Ac and the side-chain residues α-D-Galp (O56 PS) and α-D-Glcp (O25 PS), respectively. The strong long-range spatial contacts caused the unusual chemical shifts of H-3eq and C-3 of Neu5Ac.
Escherichia coli, NMR spectroscopy, polysaccharide structure, 024 and 056 antigens
Structure type: oligomer
Location inside paper: p.76, hexasaccharide II, table 4
Contained glycoepitopes: IEDB_135813,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_983931,SB_192
Methods: NMR-2D, NMR, sugar analysis, Smith degradation
Comments, role: NMR temperature was not specified; carbon 8 in bXNeup at #RE has a -10.2 ppm mismatch in 13C spectra (experiment: 62.4; hybrid simulation in water: 72.6, trust 60%); carbon 8 in aXNeup at #7,3,3 has a -10.6 ppm mismatch in 13C spectra (experiment: 62.4; hybrid simulation in water: 73, trust 60%)
Related record ID(s): 326, 327, 328, 8382, 8411, 8412, 8414
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G10613SF
Show glycosyltransferases
NMR conditions: in D2O; pH 6
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
7,3,3,7,3 bDGlcp 104.6 74.3 76.9 70.86 77.3 61.9-62.1
7,3,3,7,2 Ac
7,3,3,7 bDGlcpN 102.75 56.4 84.4 70.0 76.6 61.9-62.1
7,3,3,5 Ac
7,3,3 Subst 175.0 101.2 40.1 69.2 53.5 73.9 78.4 ?
7,3 bDGlcp 103.8 73.2 81.3 69.6 77.0 61.9-62.1
7,2 Ac
7 bDGlcpN 102.1 56.4 83.4 69.95 76.7 62.2
5 Ac
bDSugp 175.0 96.7 40.1 67.9 54.6 71.0 79.4 62.4
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
7,3,3,7,3 bDGlcp 4.47 3.31 3.50 3.42 3.48 3.67-3.90
7,3,3,7,2 Ac
7,3,3,7 bDGlcpN 4.75 3.76 3.79 3.54 3.46 3.70-3.92
7,3,3,5 Ac
7,3,3 Subst - - 1.88-2.72 3.82 3.92 3.90 3.94 3.68
7,3 bDGlcp 4.57 3.30 3.99 3.44 3.50 ?
7,2 Ac
7 bDGlcpN 4.75 3.76 3.84 3.54 3.47 3.70-3.92
5 Ac
bDSugp - - 1.66-2.29 4.18 3.81 4.23 3.98 3.65
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
7,3,3,7,3 bDGlcp 104.6/4.47 74.3/3.31 76.9/3.50 70.86/3.42 77.3/3.48 61.9-62.1/3.67-3.90
7,3,3,7,2 Ac
7,3,3,7 bDGlcpN 102.75/4.75 56.4/3.76 84.4/3.79 70.0/3.54 76.6/3.46 61.9-62.1/3.70-3.92
7,3,3,5 Ac
7,3,3 Subst 40.1/1.88-2.72 69.2/3.82 53.5/3.92 73.9/3.90 78.4/3.94 ?/3.68
7,3 bDGlcp 103.8/4.57 73.2/3.30 81.3/3.99 69.6/3.44 77.0/3.50 61.9-62.1/?
7,2 Ac
7 bDGlcpN 102.1/4.75 56.4/3.76 83.4/3.84 69.95/3.54 76.7/3.47 62.2/3.70-3.92
5 Ac
bDSugp 40.1/1.66-2.29 67.9/4.18 54.6/3.81 71.0/4.23 79.4/3.98 62.4/3.65
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 7,3,3,7,3 | bDGlcp | 4.47 | 3.31 | 3.50 | 3.42 | 3.48 | 3.67
3.90 | |
| 7,3,3,7,2 | Ac | |
| 7,3,3,7 | bDGlcpN | 4.75 | 3.76 | 3.79 | 3.54 | 3.46 | 3.70
3.92 | |
| 7,3,3,5 | Ac | |
| 7,3,3 | Subst |
|
| 1.88
2.72 | 3.82 | 3.92 | 3.90 | 3.94 | 3.68 |
| 7,3 | bDGlcp | 4.57 | 3.30 | 3.99 | 3.44 | 3.50 | ? | |
| 7,2 | Ac | |
| 7 | bDGlcpN | 4.75 | 3.76 | 3.84 | 3.54 | 3.47 | 3.70
3.92 | |
| 5 | Ac | |
| | bDSugp |
|
| 1.66
2.29 | 4.18 | 3.81 | 4.23 | 3.98 | 3.65 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 7,3,3,7,3 | bDGlcp | 104.6 | 74.3 | 76.9 | 70.86 | 77.3 | 61.9
62.1 | |
| 7,3,3,7,2 | Ac | |
| 7,3,3,7 | bDGlcpN | 102.75 | 56.4 | 84.4 | 70.0 | 76.6 | 61.9
62.1 | |
| 7,3,3,5 | Ac | |
| 7,3,3 | Subst | 175.0 | 101.2 | 40.1 | 69.2 | 53.5 | 73.9 | 78.4 | ? |
| 7,3 | bDGlcp | 103.8 | 73.2 | 81.3 | 69.6 | 77.0 | 61.9
62.1 | |
| 7,2 | Ac | |
| 7 | bDGlcpN | 102.1 | 56.4 | 83.4 | 69.95 | 76.7 | 62.2 | |
| 5 | Ac | |
| | bDSugp | 175.0 | 96.7 | 40.1 | 67.9 | 54.6 | 71.0 | 79.4 | 62.4 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":104.6,"l":"1","c":[0,0,225]},{"s":74.3,"l":"2","c":[0,0,225]},{"s":76.9,"l":"3","c":[0,0,225]},{"s":70.86,"l":"4","c":[0,0,225]},{"s":77.3,"l":"5","c":[0,0,225]},{"s":62,"l":"6","c":[0,0,225]},{"s":102.75,"l":"1","c":[230,0,30]},{"s":56.4,"l":"2","c":[230,0,30]},{"s":84.4,"l":"3","c":[230,0,30]},{"s":70,"l":"4","c":[230,0,30]},{"s":76.6,"l":"5","c":[230,0,30]},{"s":62,"l":"6","c":[230,0,30]},{"s":175,"l":"1","c":[0,165,0]},{"s":101.2,"l":"2","c":[0,165,0]},{"s":40.1,"l":"3","c":[0,165,0]},{"s":69.2,"l":"4","c":[0,165,0]},{"s":53.5,"l":"5","c":[0,165,0]},{"s":73.9,"l":"6","c":[0,165,0]},{"s":78.4,"l":"7","c":[0,165,0]},{"s":103.8,"l":"1","c":[120,0,225]},{"s":73.2,"l":"2","c":[120,0,225]},{"s":81.3,"l":"3","c":[120,0,225]},{"s":69.6,"l":"4","c":[120,0,225]},{"s":77,"l":"5","c":[120,0,225]},{"s":62,"l":"6","c":[120,0,225]},{"s":102.1,"l":"1","c":[0,192,255]},{"s":56.4,"l":"2","c":[0,192,255]},{"s":83.4,"l":"3","c":[0,192,255]},{"s":69.95,"l":"4","c":[0,192,255]},{"s":76.7,"l":"5","c":[0,192,255]},{"s":62.2,"l":"6","c":[0,192,255]},{"s":175,"l":"1","c":[220,0,180]},{"s":96.7,"l":"2","c":[220,0,180]},{"s":40.1,"l":"3","c":[220,0,180]},{"s":67.9,"l":"4","c":[220,0,180]},{"s":54.6,"l":"5","c":[220,0,180]},{"s":71,"l":"6","c":[220,0,180]},{"s":79.4,"l":"7","c":[220,0,180]},{"s":62.4,"l":"8","c":[220,0,180]}])
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
