Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infection due to Escherichia coli [ICD11:
XN6P4 
]
The structure was elucidated in this paperNCBI PubMed ID: 17056022Publication DOI: 10.1016/j.carres.2006.09.023Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: andrew.almond
manchester.ac.uk
Institutions: Faculty of Life Sciences, Manchester Interdisciplinary Biocentre, University of Manchester, Princess Street, Manchester M1 7DN, UK, The Henry Wellcome Building for Biomolecular NMR Spectroscopy, CR-UK Institute for Cancer Studies, University of Birmingham, Vincent Drive, Edgbaston, Birmingham B15 2TT, UK
The glycosaminoglycan hyaluronan is involved in a diverse range of physiological and diseases processes and comprises repeated disaccharide units of N-acetyl-d-glucosamine (GlcNAc) and d-glucuronic acid (GlcA). A molecular description of the solution conformation of HA is required to account for this biology, which is best attained using nuclear magnetic resonance (NMR). NMR studies of the polymer, however, are frustrated by resonance overlap arising from the highly degenerate structure. In contrast, end-effects in oligosaccharides can produce some chemical shift dispersion, giving the possibility that their conformational properties can be measured and extrapolated to models of the polymer. We report the complete resolution and assignment of (1)H, (13)C and (15)N nuclei in hyaluronan oligosaccharides with seven different naturally occurring terminal rings. At 900MHz, all (1)H nuclei in the hexasaccharide GlcA-β-(1→3)-GlcNAc-β-(1→4)-GlcA-β-(1→3)-GlcNAc-β-(1→4)-GlcA-β-(1→3)-GlcNAc-OH were uniquely resolved and the two central rings were found to be a good model for the polymer environment. These assignments now allow resolved, unambiguous structural restraints to be acquired on this oligosaccharide and extrapolated to models for the solution conformation of the polymer.
coupling constant, resolution, hyaluronan, strong coupling, end-effect
Structure type: oligomer
Location inside paper: p.2804, fig.1, 2
Trivial name: hyaluronan
Contained glycoepitopes: IEDB_115136,IEDB_135813,IEDB_137340,IEDB_140630,IEDB_141807,IEDB_151527,IEDB_151531,IEDB_423153
Methods: NMR
Comments, role: the published 13C NMR spectrum indirectly calibrated against DSS was shifted 1.6 ppm upfield by CSDB staff, to accord to a TMS reference. NMR data for ?DGlcpA residue 1H: #0_aDGlcpA 5.196 3.596 3.760 3.717 4.065 -//, 13C: #0_?DGlcpA 94.773 73.843 73.670 83.145 74.780 ?//; 1H: #0_bDGlcpA 4.620 3.299 3.573 3.742 3.707 -//, 13C: #_bDGlcpA 98.842 76.482 76.552 82.878 79.513 ?//
3D data: 3D data
Related record ID(s): 20007, 20301, 20303, 20304, 20305, 20306
NCBI Taxonomy refs (TaxIDs): 562Reference(s) to other database(s): GTC:G51352HP, GlycomeDB:
17865
Show glycosyltransferases
NMR conditions: in D2O; pH 6 at 297 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
4,3 bDGlcpA 104.11 73.84 76.45 72.83 76.86 ?
4,2 Ac ? 23.61
4 bDGlcpN 101.61 55.35 84.19 69.68 76.56 61.69
?DGlcpA
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
4,3 bDGlcpA 4.458 3.317 3.492 3.494 3.720 -
4,2 Ac - 2.025
4 bDGlcpN 4.560 3.843 3.710 3.539 3.482 3.775-3.920
?DGlcpA
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
4,3 bDGlcpA 104.11/4.458 73.84/3.317 76.45/3.492 72.83/3.494 76.86/3.720
4,2 Ac 23.61/2.025
4 bDGlcpN 101.61/4.560 55.35/3.843 84.19/3.710 69.68/3.539 76.56/3.482 61.69/3.775-3.920
?DGlcpA
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 4,3 | bDGlcpA | 4.458 | 3.317 | 3.492 | 3.494 | 3.720 |
|
| 4,2 | Ac |
| 2.025 | |
| 4 | bDGlcpN | 4.560 | 3.843 | 3.710 | 3.539 | 3.482 | 3.775
3.920 |
| | ?DGlcpA | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 4,3 | bDGlcpA | 104.11 | 73.84 | 76.45 | 72.83 | 76.86 | ? |
| 4,2 | Ac | ? | 23.61 | |
| 4 | bDGlcpN | 101.61 | 55.35 | 84.19 | 69.68 | 76.56 | 61.69 |
| | ?DGlcpA | |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":104.11,"l":"1","c":[0,0,225]},{"s":73.84,"l":"2","c":[0,0,225]},{"s":76.45,"l":"3","c":[0,0,225]},{"s":72.83,"l":"4","c":[0,0,225]},{"s":76.86,"l":"5","c":[0,0,225]},{"s":23.61,"l":"2","c":[0,0,0]},{"s":101.61,"l":"1","c":[230,0,30]},{"s":55.35,"l":"2","c":[230,0,30]},{"s":84.19,"l":"3","c":[230,0,30]},{"s":69.68,"l":"4","c":[230,0,30]},{"s":76.56,"l":"5","c":[230,0,30]},{"s":61.69,"l":"6","c":[230,0,30]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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