Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperPublication DOI: 10.1016/0144-8617(92)90187-UJournal NLM ID: 8307156Publisher: Elsevier
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Max-Planck-Institut für Immunbiologie, D-7800 Freiburg, FRG
The O-specific polysaccharide moiety of the O1A1 antigen (lipopolysaccharide) from E. coli 01:K1 consists of L-rhamnose, N-acetyl-d-glucosamine and N-acetyl-d-mannosamine in the molar ratio of 3:1:1. By using fragmentation procedures, methylation analysis, and NMR spectroscopy, the O1A1 polysaccharide was found to have the structure [formula: see text].
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_135610,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_225177,IEDB_885813,IEDB_885823
Methods: 13C NMR, 1H NMR, methylation, periodate oxidation, GLC-MS, NMR-2D, sugar analysis, Smith degradation, de-N-acetylation/deamination
Comments, role: published polymerization frame was shifted for conformity with other records.
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G57484QO, GlycomeDB:
6035
Show glycosyltransferases
NMR conditions: in D2O at 333 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,3,3,2,2 Ac 175.80-176.40 23.20-23.40
4,3,3,2 bDManpN 101.05 54.30 73.25 69.30 77.30 62.20
4,3,3 aLRhap 102.50 78.10 80.30 72.45 70.45 17.80-17.90
4,3 aLRhap 103.20 71.10 79.35 72.60 70.40 17.80-17.90
4 bLRhap 101.60 71.70 81.50 72.30 73.25 17.80-17.90
2 Ac 175.80-176.40 23.20-23.40
bDGlcpN 103.15 57.30 74.80 78.20 75.80 61.70
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,3,3,2,2 Ac
4,3,3,2 bDManpN 5.00 4.50 3.76 3.46 3.32 3.80-3.90
4,3,3 aLRhap 5.12 4.30 3.92 3.41 3.81 1.24
4,3 aLRhap 4.96 4.07 3.85 3.49 3.86 1.28
4 bLRhap 4.85 4.10 3.58 3.43 3.73 1.20
2 Ac
bDGlcpN 4.73 3.60-3.71 3.60-3.71 3.60-3.71 3.46-3.52 3.70-3.90
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,3,3,2,2 Ac NMR TSV error 2: unequal length of 13C and 1H datasets
4,3,3,2 bDManpN 101.05/5.00 54.30/4.50 73.25/3.76 69.30/3.46 77.30/3.32 62.20/3.80-3.90
4,3,3 aLRhap 102.50/5.12 78.10/4.30 80.30/3.92 72.45/3.41 70.45/3.81 17.80-17.90/1.24
4,3 aLRhap 103.20/4.96 71.10/4.07 79.35/3.85 72.60/3.49 70.40/3.86 17.80-17.90/1.28
4 bLRhap 101.60/4.85 71.70/4.10 81.50/3.58 72.30/3.43 73.25/3.73 17.80-17.90/1.20
2 Ac NMR TSV error 2: unequal length of 13C and 1H datasets
bDGlcpN 103.15/4.73 57.30/3.60-3.71 74.80/3.60-3.71 78.20/3.60-3.71 75.80/3.46-3.52 61.70/3.70-3.90
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,3,3,2,2 | Ac | |
| 4,3,3,2 | bDManpN | 5.00 | 4.50 | 3.76 | 3.46 | 3.32 | 3.80
3.90 |
| 4,3,3 | aLRhap | 5.12 | 4.30 | 3.92 | 3.41 | 3.81 | 1.24 |
| 4,3 | aLRhap | 4.96 | 4.07 | 3.85 | 3.49 | 3.86 | 1.28 |
| 4 | bLRhap | 4.85 | 4.10 | 3.58 | 3.43 | 3.73 | 1.20 |
| 2 | Ac | |
| | bDGlcpN | 4.73 | 3.60
3.71 | 3.60
3.71 | 3.60
3.71 | 3.46
3.52 | 3.70
3.90 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,3,3,2,2 | Ac | 175.80
176.40 | 23.20
23.40 | |
| 4,3,3,2 | bDManpN | 101.05 | 54.30 | 73.25 | 69.30 | 77.30 | 62.20 |
| 4,3,3 | aLRhap | 102.50 | 78.10 | 80.30 | 72.45 | 70.45 | 17.80
17.90 |
| 4,3 | aLRhap | 103.20 | 71.10 | 79.35 | 72.60 | 70.40 | 17.80
17.90 |
| 4 | bLRhap | 101.60 | 71.70 | 81.50 | 72.30 | 73.25 | 17.80
17.90 |
| 2 | Ac | 175.80
176.40 | 23.20
23.40 | |
| | bDGlcpN | 103.15 | 57.30 | 74.80 | 78.20 | 75.80 | 61.70 |
|
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
