Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 7528642Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Max-Planck-Institut für Immunobiologie, Freiburg, Germany
The polysaccharide moiety of the O16 antigen (lipopolysaccharide) consists of D-glucopyranose, D-galactofuranose, L-rhamnopyranose, and 2-acetamido-2-deoxy-D-glucopyranose in the molar ratios 1:1:1:1. It is O-acetylated with one acetyl group per repeating unit. One- and two-dimensional NMR spectroscopy of the polysaccharide before and after O-deacetylation showed that the O16 polysaccharide has the structure [formula: see text]
Lipopolysaccharide, LPS, Escherichia, Escherichia coli, NMR spectroscopy, polysaccharide structure, O16 antigen
Structure type: polymer chemical repeating unit
Location inside paper: p.305, abstract, p.308
Compound class: O-polysaccharide, O-antigen, LPS
Contained glycoepitopes: IEDB_130422,IEDB_136095,IEDB_136105,IEDB_137340,IEDB_137472,IEDB_141807,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_158539,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, sugar analysis, GLC, NMR-1D
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G45003OX, GlycomeDB:
6788, CCSD:
34634, CBank-STR:9131
Show glycosyltransferases
NMR conditions: in D2O at 338 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
2,3,3 aDGlcp 96.9 72.9 74.2 70.8 71.7 67.3
2,3,2 Ac 174.2 21.5
2,3 aLRhap 99.6 70.1 75.1 71.9 70.0 17.8
2,2 Ac 175.4 23.4
2 aDGlcpN 98.3 54.1 80.8 69.7 74.1 62.0
bDGalf 107.2 87.8 76.7 83.7 71.7 64.2
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
2,3,3 aDGlcp 4.95 3.54 3.69 3.48 3.99 3.72-3.95
2,3,2 Ac
2,3 aLRhap 4.92 5.12 3.94 3.60 4.08 1.28
2,2 Ac
2 aDGlcpN 4.96 4.13 3.76 3.61 3.79 3.85-3.95
bDGalf 5.07 4.14 4.24 4.01 3.88 3.68-3.73
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
2,3,3 aDGlcp 96.9/4.95 72.9/3.54 74.2/3.69 70.8/3.48 71.7/3.99 67.3/3.72-3.95
2,3,2 Ac NMR TSV error 2: unequal length of 13C and 1H datasets
2,3 aLRhap 99.6/4.92 70.1/5.12 75.1/3.94 71.9/3.60 70.0/4.08 17.8/1.28
2,2 Ac NMR TSV error 2: unequal length of 13C and 1H datasets
2 aDGlcpN 98.3/4.96 54.1/4.13 80.8/3.76 69.7/3.61 74.1/3.79 62.0/3.85-3.95
bDGalf 107.2/5.07 87.8/4.14 76.7/4.24 83.7/4.01 71.7/3.88 64.2/3.68-3.73
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 2,3,3 | aDGlcp | 4.95 | 3.54 | 3.69 | 3.48 | 3.99 | 3.72
3.95 |
| 2,3,2 | Ac | |
| 2,3 | aLRhap | 4.92 | 5.12 | 3.94 | 3.60 | 4.08 | 1.28 |
| 2,2 | Ac | |
| 2 | aDGlcpN | 4.96 | 4.13 | 3.76 | 3.61 | 3.79 | 3.85
3.95 |
| | bDGalf | 5.07 | 4.14 | 4.24 | 4.01 | 3.88 | 3.68
3.73 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 2,3,3 | aDGlcp | 96.9 | 72.9 | 74.2 | 70.8 | 71.7 | 67.3 |
| 2,3,2 | Ac | 174.2 | 21.5 | |
| 2,3 | aLRhap | 99.6 | 70.1 | 75.1 | 71.9 | 70.0 | 17.8 |
| 2,2 | Ac | 175.4 | 23.4 | |
| 2 | aDGlcpN | 98.3 | 54.1 | 80.8 | 69.7 | 74.1 | 62.0 |
| | bDGalf | 107.2 | 87.8 | 76.7 | 83.7 | 71.7 | 64.2 |
|
There is only one chemically distinct structure:
Found 
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