Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: infectious bovine keratoconjunctivitis [ICD11:
9A60.3Z 
, ICD11:
9A60.Y ];
infection due to Moraxella [ICD11:
XN90V ]
The structure was elucidated in this paperNCBI PubMed ID: 33839496Publication DOI: 10.1016/j.carres.2021.108293Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: J.C. Wilson <jennifer.wilson
griffith.edu.au>
Institutions: Institute for Glycomics, Griffith University, Gold Coast Campus, Queensland, 4222, Australia, School of Medical Science, Griffith University, Gold Coast Campus, Queensland, 4222, Australia, Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126, Napoli, Italy, Department of Agricultural Sciences, University of Naples Federico II, Via Universita, 100, 80055, Portici, Italy
The Gram-negative bacterium Moraxella bovoculi is associated with infectious bovine keratoconjunctivitis (IBK), colloquially known as 'pink-eye'. IBK is an extremely contagious ocular disease of cattle. We report here the structure of the oligosaccharide derived from the lipooligosaccharide from M. bovoculi type strain 237 (also known as ATCC BAA-1259T). GLC-MS and correlation NMR analysis of the oligosaccharide revealed 5 sugar residues, with a notable central branched 3,4,6-α-D-Glcp. An additional α-D-Manp was present ~30% on the sub-terminal α-D-Manp of the 4-linked branch. This oligosaccharide structure was consistent with other members of the Moraxellaceae where no heptose was present and 5-linked Kdo was directly attached to the central 3,4,6-α-D-Glcp.
Lipooligosaccharide, LOS, NMR spectroscopy, endotoxin, Structural characterization, Infectious bovine keratoconjunctivitis, dairy cattle, IBK, Moraxella bovoculi, Pinkeye
Structure type: oligomer
Location inside paper: Fig. 1, table 1
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130701,IEDB_141793,IEDB_141806,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_153220,IEDB_153543,IEDB_983930,IEDB_983931,SB_192,SB_198,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, GLC-MS, NMR-2D, chemical analysis, TLC, enzymatic digestion, SEC, genome analysis
Comments, role: In Table 1, NMR chemical shifts of all bDGlcp residues seem to be erroneous (swapped C3 and C4; corrected by CSDB staff).
NCBI Taxonomy refs (TaxIDs): 743974
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
5,3 bDGlcp 101.1 74.1 76.9 70.7 76.9 61.5
5,4,6,6 30%aDManp 100.6 71.3 71.9 68.1 73.9 62.0
5,4,6 aDManp 100.8 71.1 71.9 67.9 72.1 66.6
5,4 bDGlcp 102.7 74.4 77.1 70.1 75.1 65.7
5,6 bDGlcp 103.4 74.2 77.1 71.0 77.0 61.9
5 aDGlcp 100.7 73.8 76.2 75.8 70.9 67.1
aXKdo? ? ? 35.0 67.1 76.8 71.2 69.9 65.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
5,3 bDGlcp 5.00 3.34 3.41 3.53 3.48 3.73-3.94
5,4,6,6 30%aDManp 4.93 3.97 3.85 3.67 3.70 3.78-3.89
5,4,6 aDManp 4.89 3.06 3.85 3.72 3.80 3.80-3.95
5,4 bDGlcp 4.69 3.37 3.55 3.49 3.58 3.73-4.05
5,6 bDGlcp 4.50 3.32 3.40 3.51 3.46 3.73-3.92
5 aDGlcp 5.14 3.81 4.30 3.97 4.44 4.05-4.17
aXKdo? - - 1.88-2.38 4.17 4.09 3.85 4.05 3.63-3.80
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
5,3 bDGlcp 101.1/5.00 74.1/3.34 76.9/3.41 70.7/3.53 76.9/3.48 61.5/3.73-3.94
5,4,6,6 30%aDManp 100.6/4.93 71.3/3.97 71.9/3.85 68.1/3.67 73.9/3.70 62.0/3.78-3.89
5,4,6 aDManp 100.8/4.89 71.1/3.06 71.9/3.85 67.9/3.72 72.1/3.80 66.6/3.80-3.95
5,4 bDGlcp 102.7/4.69 74.4/3.37 77.1/3.55 70.1/3.49 75.1/3.58 65.7/3.73-4.05
5,6 bDGlcp 103.4/4.50 74.2/3.32 77.1/3.40 71.0/3.51 77.0/3.46 61.9/3.73-3.92
5 aDGlcp 100.7/5.14 73.8/3.81 76.2/4.30 75.8/3.97 70.9/4.44 67.1/4.05-4.17
aXKdo? 35.0/1.88-2.38 67.1/4.17 76.8/4.09 71.2/3.85 69.9/4.05 65.3/3.63-3.80
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 5,3 | bDGlcp | 5.00 | 3.34 | 3.41 | 3.53 | 3.48 | 3.73
3.94 | |
| 5,4,6,6 | 30%aDManp | 4.93 | 3.97 | 3.85 | 3.67 | 3.70 | 3.78
3.89 | |
| 5,4,6 | aDManp | 4.89 | 3.06 | 3.85 | 3.72 | 3.80 | 3.80
3.95 | |
| 5,4 | bDGlcp | 4.69 | 3.37 | 3.55 | 3.49 | 3.58 | 3.73
4.05 | |
| 5,6 | bDGlcp | 4.50 | 3.32 | 3.40 | 3.51 | 3.46 | 3.73
3.92 | |
| 5 | aDGlcp | 5.14 | 3.81 | 4.30 | 3.97 | 4.44 | 4.05
4.17 | |
| | aXKdo? |
|
| 1.88
2.38 | 4.17 | 4.09 | 3.85 | 4.05 | 3.63
3.80 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 5,3 | bDGlcp | 101.1 | 74.1 | 76.9 | 70.7 | 76.9 | 61.5 | |
| 5,4,6,6 | 30%aDManp | 100.6 | 71.3 | 71.9 | 68.1 | 73.9 | 62.0 | |
| 5,4,6 | aDManp | 100.8 | 71.1 | 71.9 | 67.9 | 72.1 | 66.6 | |
| 5,4 | bDGlcp | 102.7 | 74.4 | 77.1 | 70.1 | 75.1 | 65.7 | |
| 5,6 | bDGlcp | 103.4 | 74.2 | 77.1 | 71.0 | 77.0 | 61.9 | |
| 5 | aDGlcp | 100.7 | 73.8 | 76.2 | 75.8 | 70.9 | 67.1 | |
| | aXKdo? | ? | ? | 35.0 | 67.1 | 76.8 | 71.2 | 69.9 | 65.3 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":101.1,"l":"1","c":[0,0,225]},{"s":74.1,"l":"2","c":[0,0,225]},{"s":76.9,"l":"3","c":[0,0,225]},{"s":70.7,"l":"4","c":[0,0,225]},{"s":76.9,"l":"5","c":[0,0,225]},{"s":61.5,"l":"6","c":[0,0,225]},{"s":100.6,"l":"1","c":[230,0,30]},{"s":71.3,"l":"2","c":[230,0,30]},{"s":71.9,"l":"3","c":[230,0,30]},{"s":68.1,"l":"4","c":[230,0,30]},{"s":73.9,"l":"5","c":[230,0,30]},{"s":62,"l":"6","c":[230,0,30]},{"s":100.8,"l":"1","c":[0,165,0]},{"s":71.1,"l":"2","c":[0,165,0]},{"s":71.9,"l":"3","c":[0,165,0]},{"s":67.9,"l":"4","c":[0,165,0]},{"s":72.1,"l":"5","c":[0,165,0]},{"s":66.6,"l":"6","c":[0,165,0]},{"s":102.7,"l":"1","c":[120,0,225]},{"s":74.4,"l":"2","c":[120,0,225]},{"s":77.1,"l":"3","c":[120,0,225]},{"s":70.1,"l":"4","c":[120,0,225]},{"s":75.1,"l":"5","c":[120,0,225]},{"s":65.7,"l":"6","c":[120,0,225]},{"s":103.4,"l":"1","c":[0,192,255]},{"s":74.2,"l":"2","c":[0,192,255]},{"s":77.1,"l":"3","c":[0,192,255]},{"s":71,"l":"4","c":[0,192,255]},{"s":77,"l":"5","c":[0,192,255]},{"s":61.9,"l":"6","c":[0,192,255]},{"s":100.7,"l":"1","c":[220,0,180]},{"s":73.8,"l":"2","c":[220,0,180]},{"s":76.2,"l":"3","c":[220,0,180]},{"s":75.8,"l":"4","c":[220,0,180]},{"s":70.9,"l":"5","c":[220,0,180]},{"s":67.1,"l":"6","c":[220,0,180]},{"s":35,"l":"3","c":[100,160,0]},{"s":67.1,"l":"4","c":[100,160,0]},{"s":76.8,"l":"5","c":[100,160,0]},{"s":71.2,"l":"6","c":[100,160,0]},{"s":69.9,"l":"7","c":[100,160,0]},{"s":65.3,"l":"8","c":[100,160,0]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
