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Grice ID, Peak IR, King RM, Ravikumaran KS, Speciale I, Molinaro A, De Castro C, Wilson JC
Structural characterisation of the oligosaccharide from Moraxella bovoculi type strain 237 (ATCC BAA-1259) lipooligosaccharide
Carbohydrate Research 503 (2021)
108293
|
b-D-Glcp-(1-3)-+
|
30%a-D-Manp-(1-6)-a-D-Manp-(1-6)-b-D-Glcp-(1-4)-a-D-Glcp-(1-5)-a-Kdo
|
b-D-Glcp-(1-6)-+ |
Show graphically |
Moraxella bovoculi 237 (ATCC BAA-1259)
(NCBI TaxID 743974,
species name lookup)
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:
Expand this record
Collapse this record
Faglin I, Grice ID, Ratnayake SR, Daal TM, Singh S, Wilson JC, Peak IR
Identification and characterisation of a biosynthetic locus for Moraxella bovis lipo-oligosaccharide
Carbohydrate Research 421 (2016)
9-16
|
a-D-Glcp-(1-2)-b-D-Glcp-(1-4)-+
|
a-D-Glcp-(1-2)-+ |
| |
D-GalaNAc-(1-4:1-6)-a-D-Galp-(1-4)-b-D-Galp-(1-4)-b-D-Glcp-(1-4)-a-D-Glcp-(1-2)-b-D-Glcp-(1-6)-a-D-Glcp-(1-5)-a-Kdo
xDGalaN = S-D-GalN (open chain) |
Show graphically |
Moraxella bovis Epp63
(NCBI TaxID 387425,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Bos taurus
Associated disease: infectious bovine keratoconjunctivitis [ICD11:
9A60.3Z , ICD11:
9A60.Y ];
infection due to Moraxella [ICD11:
XN90V ]
NCBI PubMed ID: 26774874Publication DOI: 10.1016/j.carres.2015.12.003Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: jennifer.wilson
griffith.edu.au; i.peak
griffith.edu.au
Institutions: Menzies Health Institute, Molecular Basis of Disease, Griffith University, Gold Coast Campus, Southport, Qld. 4222, Australia, Institute for Glycomics, Griffith University, Gold Coast Campus, Southport, Qld. 4222, Australia, School of Medical Science, Griffith University, Gold Coast Campus, Southport, Qld. 4222, Australia
Moraxella bovis is a Gram-negative gammaproteobacterium and is one of the causative agents of infectious bovine keratoconjunctivitis. The structure of lipooligosaccharide (LOS) from strain Epp63 was recently elucidated. In the present study a genetic locus of seven encoding genes with high similarity to glycosyltransferases has been identified. Mutation of these putative glycosyltransferase genes resulted in M. bovis mutant bacteria that expressed truncated LOS structures. The structures of the oligosaccharide (OS) expressed by the mutant strains were elucidated and demonstrated the role of the glycosyltransferase enzymes in the LOS biosynthesis of M. bovis. The glycosyltransferase genes designated lgt1, lgt3, and lgt6 are highly similar to the genes in the related bacterium M. catarrhalis. In addition, there are syntenic similarities with the corresponding LOS biosynthesis locus in M. catarrhalis and other members of Moraxellaceae.
Lipooligosaccharide, glycosyltransferase, lipo-oligosaccharide, Infectious bovine keratoconjunctivitis, Moraxella bovis
Structure type: oligomer
Location inside paper: p.12, fig.3, p.13, fig.4A
Compound class: LOS
Contained glycoepitopes: IEDB_130650,IEDB_130651,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_137473,IEDB_1391964,IEDB_141794,IEDB_141806,IEDB_142487,IEDB_142488,IEDB_144987,IEDB_144998,IEDB_146664,IEDB_151528,IEDB_152217,IEDB_190606,IEDB_232584,IEDB_423106,IEDB_742247,IEDB_983931,SB_165,SB_166,SB_167,SB_178,SB_187,SB_192,SB_195,SB_31,SB_6,SB_62,SB_7,SB_88
Methods: 13C NMR, 1H NMR, NMR-2D, PCR, SDS-PAGE, sugar analysis, acid hydrolysis, NMR-1D, genetic methods, GPC, bioinformatic analysis, SEC
Biological activity: the role of the glycosyltransferase enzymes in the LOS biosynthesis of M. bovis
Related record ID(s): 11597, 11598, 11599
NCBI Taxonomy refs (TaxIDs): 387425
Show glycosyltransferases
There is only one chemically distinct structure:
Expand this record
Collapse this record
Faglin I, Grice ID, Ratnayake SR, Daal TM, Singh S, Wilson JC, Peak IR
Identification and characterisation of a biosynthetic locus for Moraxella bovis lipo-oligosaccharide
Carbohydrate Research 421 (2016)
9-16
Moraxella bovis 63.1∆
(Ancestor NCBI TaxID 476,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Bos taurus
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: 26774874Publication DOI: 10.1016/j.carres.2015.12.003Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: jennifer.wilson
griffith.edu.au; i.peak
griffith.edu.au
Institutions: Menzies Health Institute, Molecular Basis of Disease, Griffith University, Gold Coast Campus, Southport, Qld. 4222, Australia, Institute for Glycomics, Griffith University, Gold Coast Campus, Southport, Qld. 4222, Australia, School of Medical Science, Griffith University, Gold Coast Campus, Southport, Qld. 4222, Australia
Moraxella bovis is a Gram-negative gammaproteobacterium and is one of the causative agents of infectious bovine keratoconjunctivitis. The structure of lipooligosaccharide (LOS) from strain Epp63 was recently elucidated. In the present study a genetic locus of seven encoding genes with high similarity to glycosyltransferases has been identified. Mutation of these putative glycosyltransferase genes resulted in M. bovis mutant bacteria that expressed truncated LOS structures. The structures of the oligosaccharide (OS) expressed by the mutant strains were elucidated and demonstrated the role of the glycosyltransferase enzymes in the LOS biosynthesis of M. bovis. The glycosyltransferase genes designated lgt1, lgt3, and lgt6 are highly similar to the genes in the related bacterium M. catarrhalis. In addition, there are syntenic similarities with the corresponding LOS biosynthesis locus in M. catarrhalis and other members of Moraxellaceae.
Lipooligosaccharide, glycosyltransferase, lipo-oligosaccharide, Infectious bovine keratoconjunctivitis, Moraxella bovis
Structure type: oligomer
Location inside paper: p.12, fig.3, 63.1∆
Compound class: LOS
Contained glycoepitopes: IEDB_130650,IEDB_141806,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, PCR, SDS-PAGE, sugar analysis, acid hydrolysis, NMR-1D, genetic methods, GPC, bioinformatic analysis, SEC
Biological activity: the role of the glycosyltransferase enzymes in the LOS biosynthesis of M. bovis
Related record ID(s): 11254, 11598, 11599
NCBI Taxonomy refs (TaxIDs): 476Reference(s) to other database(s): GTC:G74587GM
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
5,4 bDGlcp 103.2 74.1 76.6 70.5 76.8 61.7
5,6 bDGlcp 103.2 74.1 76.8 70.6 76.8 61.7
5 aDGlcp 100.4 72.7 72.6 78.8 70.4 68.0
aXKdo? ? ? 40.2 67.1 76.5 72.6 68.5 63.5
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
5,4 bDGlcp 4.58 3.26 3.50 3.39 3.45 3.74-3.93
5,6 bDGlcp 4.49 3.23 3.49 3.39 3.44 3.72-3.92
5 aDGlcp 5.13 3.58 3.89 3.77 4.36 3.98-4.13
aXKdo? - - 1.81-2.19 4.13 4.06 3.81 4.01 3.59-3.82
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
5,4 bDGlcp 103.2/4.58 74.1/3.26 76.6/3.50 70.5/3.39 76.8/3.45 61.7/3.74-3.93
5,6 bDGlcp 103.2/4.49 74.1/3.23 76.8/3.49 70.6/3.39 76.8/3.44 61.7/3.72-3.92
5 aDGlcp 100.4/5.13 72.7/3.58 72.6/3.89 78.8/3.77 70.4/4.36 68.0/3.98-4.13
aXKdo? 40.2/1.81-2.19 67.1/4.13 76.5/4.06 72.6/3.81 68.5/4.01 63.5/3.59-3.82
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 5,4 | bDGlcp | 4.58 | 3.26 | 3.50 | 3.39 | 3.45 | 3.74
3.93 | |
| 5,6 | bDGlcp | 4.49 | 3.23 | 3.49 | 3.39 | 3.44 | 3.72
3.92 | |
| 5 | aDGlcp | 5.13 | 3.58 | 3.89 | 3.77 | 4.36 | 3.98
4.13 | |
| | aXKdo? |
|
| 1.81
2.19 | 4.13 | 4.06 | 3.81 | 4.01 | 3.59
3.82 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 5,4 | bDGlcp | 103.2 | 74.1 | 76.6 | 70.5 | 76.8 | 61.7 | |
| 5,6 | bDGlcp | 103.2 | 74.1 | 76.8 | 70.6 | 76.8 | 61.7 | |
| 5 | aDGlcp | 100.4 | 72.7 | 72.6 | 78.8 | 70.4 | 68.0 | |
| | aXKdo? | ? | ? | 40.2 | 67.1 | 76.5 | 72.6 | 68.5 | 63.5 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":103.2,"l":"1","c":[0,0,225]},{"s":74.1,"l":"2","c":[0,0,225]},{"s":76.6,"l":"3","c":[0,0,225]},{"s":70.5,"l":"4","c":[0,0,225]},{"s":76.8,"l":"5","c":[0,0,225]},{"s":61.7,"l":"6","c":[0,0,225]},{"s":103.2,"l":"1","c":[230,0,30]},{"s":74.1,"l":"2","c":[230,0,30]},{"s":76.8,"l":"3","c":[230,0,30]},{"s":70.6,"l":"4","c":[230,0,30]},{"s":76.8,"l":"5","c":[230,0,30]},{"s":61.7,"l":"6","c":[230,0,30]},{"s":100.4,"l":"1","c":[0,165,0]},{"s":72.7,"l":"2","c":[0,165,0]},{"s":72.6,"l":"3","c":[0,165,0]},{"s":78.8,"l":"4","c":[0,165,0]},{"s":70.4,"l":"5","c":[0,165,0]},{"s":68,"l":"6","c":[0,165,0]},{"s":40.2,"l":"3","c":[120,0,225]},{"s":67.1,"l":"4","c":[120,0,225]},{"s":76.5,"l":"5","c":[120,0,225]},{"s":72.6,"l":"6","c":[120,0,225]},{"s":68.5,"l":"7","c":[120,0,225]},{"s":63.5,"l":"8","c":[120,0,225]}])
The spectrum also has 2 signals at unknown positions (not plotted). |
There is only one chemically distinct structure:
Expand this record
Collapse this record
Faglin I, Grice ID, Ratnayake SR, Daal TM, Singh S, Wilson JC, Peak IR
Identification and characterisation of a biosynthetic locus for Moraxella bovis lipo-oligosaccharide
Carbohydrate Research 421 (2016)
9-16
|
a-D-Glcp-(1-2)-b-D-Glcp-(1-4)-+
|
a-D-Glcp-(1-2)-a-D-Glcp-(1-2)-b-D-Glcp-(1-6)-a-D-Glcp-(1-5)-a-Kdo |
Show graphically |
Moraxella bovis 63.2∆
(Ancestor NCBI TaxID 476,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Bos taurus
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: 26774874Publication DOI: 10.1016/j.carres.2015.12.003Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: jennifer.wilson
griffith.edu.au; i.peak
griffith.edu.au
Institutions: Menzies Health Institute, Molecular Basis of Disease, Griffith University, Gold Coast Campus, Southport, Qld. 4222, Australia, Institute for Glycomics, Griffith University, Gold Coast Campus, Southport, Qld. 4222, Australia, School of Medical Science, Griffith University, Gold Coast Campus, Southport, Qld. 4222, Australia
Moraxella bovis is a Gram-negative gammaproteobacterium and is one of the causative agents of infectious bovine keratoconjunctivitis. The structure of lipooligosaccharide (LOS) from strain Epp63 was recently elucidated. In the present study a genetic locus of seven encoding genes with high similarity to glycosyltransferases has been identified. Mutation of these putative glycosyltransferase genes resulted in M. bovis mutant bacteria that expressed truncated LOS structures. The structures of the oligosaccharide (OS) expressed by the mutant strains were elucidated and demonstrated the role of the glycosyltransferase enzymes in the LOS biosynthesis of M. bovis. The glycosyltransferase genes designated lgt1, lgt3, and lgt6 are highly similar to the genes in the related bacterium M. catarrhalis. In addition, there are syntenic similarities with the corresponding LOS biosynthesis locus in M. catarrhalis and other members of Moraxellaceae.
Lipooligosaccharide, glycosyltransferase, lipo-oligosaccharide, Infectious bovine keratoconjunctivitis, Moraxella bovis
Structure type: oligomer
Location inside paper: p.12, fig.3, 63.2∆
Compound class: LOS
Contained glycoepitopes: IEDB_130650,IEDB_141806,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_232584,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, PCR, SDS-PAGE, sugar analysis, acid hydrolysis, NMR-1D, genetic methods, GPC, bioinformatic analysis, SEC
Biological activity: the role of the glycosyltransferase enzymes in the LOS biosynthesis of M. bovis
Related record ID(s): 11254, 11597, 11599
NCBI Taxonomy refs (TaxIDs): 476Reference(s) to other database(s): GTC:G85084BZ
Show glycosyltransferases
NMR conditions: in D2O at 298 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8
5,4,2 aDGlcp 99.6 73.0 74.5 70.8 73.0 61.6
5,4 bDGlcp 100.6 78.9 76.2 71.0 77.1 62.3
5,6,2,2 aDGlcp 96.3 73.0 74.5 70.8 73.0 62.3
5,6,2 aDGlcp 94.4 75.4 70.8 72.9 72.4 61.9
5,6 bDGlcp 103.5 75.9 76.9 70.9 76.9 62.3
5 aDGlcp 100.9 73.7 73.7 78.0 70.6 68.8
aXKdo? ? ? 40.6 67.4 76.5 72.6 69.7 64.3
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8
5,4,2 aDGlcp 5.31 3.51 3.72 3.44 4.03 3.77-3.91
5,4 bDGlcp 4.76 3.57 3.57 3.43 3.41 3.71-3.84
5,6,2,2 aDGlcp 5.21 3.55 3.78 3.43 3.94 3.86-3.91
5,6,2 aDGlcp 5.80 3.71 3.85 3.50 4.03 3.77-3.77
5,6 bDGlcp 4.64 3.57 3.42 3.67 3.42 3.72-3.90
5 aDGlcp 5.14 3.57 4.10 3.78 4.56 4.10
aXKdo? - - 1.85-2.02 4.13 4.06 3.81 4.01 3.61-3.78
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8
5,4,2 aDGlcp 99.6/5.31 73.0/3.51 74.5/3.72 70.8/3.44 73.0/4.03 61.6/3.77-3.91
5,4 bDGlcp 100.6/4.76 78.9/3.57 76.2/3.57 71.0/3.43 77.1/3.41 62.3/3.71-3.84
5,6,2,2 aDGlcp 96.3/5.21 73.0/3.55 74.5/3.78 70.8/3.43 73.0/3.94 62.3/3.86-3.91
5,6,2 aDGlcp 94.4/5.80 75.4/3.71 70.8/3.85 72.9/3.50 72.4/4.03 61.9/3.77-3.77
5,6 bDGlcp 103.5/4.64 75.9/3.57 76.9/3.42 70.9/3.67 76.9/3.42 62.3/3.72-3.90
5 aDGlcp 100.9/5.14 73.7/3.57 73.7/4.10 78.0/3.78 70.6/4.56 68.8/4.10
aXKdo? 40.6/1.85-2.02 67.4/4.13 76.5/4.06 72.6/3.81 69.7/4.01 64.3/3.61-3.78
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 |
|---|
| 5,4,2 | aDGlcp | 5.31 | 3.51 | 3.72 | 3.44 | 4.03 | 3.77
3.91 | |
| 5,4 | bDGlcp | 4.76 | 3.57 | 3.57 | 3.43 | 3.41 | 3.71
3.84 | |
| 5,6,2,2 | aDGlcp | 5.21 | 3.55 | 3.78 | 3.43 | 3.94 | 3.86
3.91 | |
| 5,6,2 | aDGlcp | 5.80 | 3.71 | 3.85 | 3.50 | 4.03 | 3.77
3.77 | |
| 5,6 | bDGlcp | 4.64 | 3.57 | 3.42 | 3.67 | 3.42 | 3.72
3.90 | |
| 5 | aDGlcp | 5.14 | 3.57 | 4.10 | 3.78 | 4.56 | 4.10 | |
| | aXKdo? |
|
| 1.85
2.02 | 4.13 | 4.06 | 3.81 | 4.01 | 3.61
3.78 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 |
|---|
| 5,4,2 | aDGlcp | 99.6 | 73.0 | 74.5 | 70.8 | 73.0 | 61.6 | |
| 5,4 | bDGlcp | 100.6 | 78.9 | 76.2 | 71.0 | 77.1 | 62.3 | |
| 5,6,2,2 | aDGlcp | 96.3 | 73.0 | 74.5 | 70.8 | 73.0 | 62.3 | |
| 5,6,2 | aDGlcp | 94.4 | 75.4 | 70.8 | 72.9 | 72.4 | 61.9 | |
| 5,6 | bDGlcp | 103.5 | 75.9 | 76.9 | 70.9 | 76.9 | 62.3 | |
| 5 | aDGlcp | 100.9 | 73.7 | 73.7 | 78.0 | 70.6 | 68.8 | |
| | aXKdo? | ? | ? | 40.6 | 67.4 | 76.5 | 72.6 | 69.7 | 64.3 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":99.6,"l":"1","c":[0,0,225]},{"s":73,"l":"2","c":[0,0,225]},{"s":74.5,"l":"3","c":[0,0,225]},{"s":70.8,"l":"4","c":[0,0,225]},{"s":73,"l":"5","c":[0,0,225]},{"s":61.6,"l":"6","c":[0,0,225]},{"s":100.6,"l":"1","c":[230,0,30]},{"s":78.9,"l":"2","c":[230,0,30]},{"s":76.2,"l":"3","c":[230,0,30]},{"s":71,"l":"4","c":[230,0,30]},{"s":77.1,"l":"5","c":[230,0,30]},{"s":62.3,"l":"6","c":[230,0,30]},{"s":96.3,"l":"1","c":[0,165,0]},{"s":73,"l":"2","c":[0,165,0]},{"s":74.5,"l":"3","c":[0,165,0]},{"s":70.8,"l":"4","c":[0,165,0]},{"s":73,"l":"5","c":[0,165,0]},{"s":62.3,"l":"6","c":[0,165,0]},{"s":94.4,"l":"1","c":[120,0,225]},{"s":75.4,"l":"2","c":[120,0,225]},{"s":70.8,"l":"3","c":[120,0,225]},{"s":72.9,"l":"4","c":[120,0,225]},{"s":72.4,"l":"5","c":[120,0,225]},{"s":61.9,"l":"6","c":[120,0,225]},{"s":103.5,"l":"1","c":[0,192,255]},{"s":75.9,"l":"2","c":[0,192,255]},{"s":76.9,"l":"3","c":[0,192,255]},{"s":70.9,"l":"4","c":[0,192,255]},{"s":76.9,"l":"5","c":[0,192,255]},{"s":62.3,"l":"6","c":[0,192,255]},{"s":100.9,"l":"1","c":[220,0,180]},{"s":73.7,"l":"2","c":[220,0,180]},{"s":73.7,"l":"3","c":[220,0,180]},{"s":78,"l":"4","c":[220,0,180]},{"s":70.6,"l":"5","c":[220,0,180]},{"s":68.8,"l":"6","c":[220,0,180]},{"s":40.6,"l":"3","c":[100,160,0]},{"s":67.4,"l":"4","c":[100,160,0]},{"s":76.5,"l":"5","c":[100,160,0]},{"s":72.6,"l":"6","c":[100,160,0]},{"s":69.7,"l":"7","c":[100,160,0]},{"s":64.3,"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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