Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 10573858Publication DOI: 10.1016/S0008-6215(99)00142-1Journal NLM ID: 0043535Publisher: 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: polymer chemical repeating unit
Location inside paper: abstract
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135813,IEDB_136045,IEDB_137340,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144998,IEDB_144999,IEDB_145002,IEDB_146664,IEDB_151531,IEDB_152214,IEDB_174333,IEDB_241118,IEDB_983931,SB_192,SB_86
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, HF solvolysis, sugar analysis, 31P NMR, ESI-MS
Related record ID(s): 318, 3219, 21773
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G35242RI, GlycomeDB:
25910
Show glycosyltransferases
NMR conditions: in D2O at 323 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
3,2,6,0,4 aLFucp 99.2 68.8 70.2 72.9 67.4 16.3
3,2,6,0 aDGlcp 96.1 73.4 77.9 72.8 73.2 60.4
3,2,6 P
3,2 aDGlcp 98.8 72.6 73.5 71.7 69.8 65.1
3 bDGlcp 102.0 78.8 75.7 70.6 76.7 61.4
2 Ac 175.5 23.3
bDGlcpN 101.8 56.4 80.0 70.1 76.1 62.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
3,2,6,0,4 aLFucp 4.97 3.76 3.86 3.77 4.84 1.25
3,2,6,0 aDGlcp 5.44 3.63 4.03 3.68 3.91 3.86
3,2,6 P
3,2 aDGlcp 5.24 3.52 3.73 4.06 3.51 4.06-4.12
3 bDGlcp 4.68 3.42 3.53 3.43 3.40 3.70-3.89
2 Ac - 2.06
bDGlcpN 4.93 3.78 3.99 3.39 3.42 3.61-3.93
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
3,2,6,0,4 aLFucp 99.2/4.97 68.8/3.76 70.2/3.86 72.9/3.77 67.4/4.84 16.3/1.25
3,2,6,0 aDGlcp 96.1/5.44 73.4/3.63 77.9/4.03 72.8/3.68 73.2/3.91 60.4/3.86
3,2,6 P
3,2 aDGlcp 98.8/5.24 72.6/3.52 73.5/3.73 71.7/4.06 69.8/3.51 65.1/4.06-4.12
3 bDGlcp 102.0/4.68 78.8/3.42 75.7/3.53 70.6/3.43 76.7/3.40 61.4/3.70-3.89
2 Ac 23.3/2.06
bDGlcpN 101.8/4.93 56.4/3.78 80.0/3.99 70.1/3.39 76.1/3.42 62.6/3.61-3.93
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 3,2,6,0,4 | aLFucp | 4.97 | 3.76 | 3.86 | 3.77 | 4.84 | 1.25 |
| 3,2,6,0 | aDGlcp | 5.44 | 3.63 | 4.03 | 3.68 | 3.91 | 3.86 |
| 3,2,6 | P | |
| 3,2 | aDGlcp | 5.24 | 3.52 | 3.73 | 4.06 | 3.51 | 4.06
4.12 |
| 3 | bDGlcp | 4.68 | 3.42 | 3.53 | 3.43 | 3.40 | 3.70
3.89 |
| 2 | Ac |
| 2.06 | |
| | bDGlcpN | 4.93 | 3.78 | 3.99 | 3.39 | 3.42 | 3.61
3.93 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 3,2,6,0,4 | aLFucp | 99.2 | 68.8 | 70.2 | 72.9 | 67.4 | 16.3 |
| 3,2,6,0 | aDGlcp | 96.1 | 73.4 | 77.9 | 72.8 | 73.2 | 60.4 |
| 3,2,6 | P | |
| 3,2 | aDGlcp | 98.8 | 72.6 | 73.5 | 71.7 | 69.8 | 65.1 |
| 3 | bDGlcp | 102.0 | 78.8 | 75.7 | 70.6 | 76.7 | 61.4 |
| 2 | Ac | 175.5 | 23.3 | |
| | bDGlcpN | 101.8 | 56.4 | 80.0 | 70.1 | 76.1 | 62.6 |
|
There is only one chemically distinct structure:
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