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Wang D, Carroll GT, Turro NJ, Koberstein JT, Kovác P, Saksena R, Adamo R, Herzenberg LA, Steinman L
Photogenerated glycan arrays identify immunogenic sugar moieties of Bacillus anthracis exosporium
Proteomics 7(2) (2007)
180-184
|
3HOiVl-(1-4)-b-D-Quip4N2Me-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1--/5-methoxycarbonylpentyl/
3HOiVl = 3-hydroxy-3-methylbutanoic acid |
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Bacillus anthracis
(NCBI TaxID 1392,
species name lookup)
Taxonomic group: bacteria / Firmicutes
(Phylum: Firmicutes)
Host organism: (mammal)
Associated disease: anthrax [ICD11:
1B97 
, ICD11:
XN94F ];
lung infections [ICD11:
CA4Y , ICD11:
CA4Z ];
infection due to Bacillus anthracis [ICD11:
XN94F ]
NCBI PubMed ID: 17205603Publication DOI: 10.1002/pmic.200600478Journal NLM ID: 101092707Publisher: Wiley-VCH
Correspondence: dwang1
stanford.edu
Institutions: Carbohydrate Microarray Laboratory, Stanford University School of Medicine, Stanford, CA, USA
Using photogenerated glycan arrays, we characterized a large panel of synthetic carbohydrates for their antigenic reactivities with pathogen-specific antibodies. We discovered that rabbit IgG antibodies elicited by Bacillus anthracis spores specifically recognize a tetrasaccharide chain that decorates the outermost surfaces of the B. anthracis exosporium. Since this sugar moiety is highly specific for the spores of B. anthracis, it appears to be a key biomarker for detection of B. anthracis spores and development of novel vaccines that target anthrax spores.
carbohydrates, antibody, bacteria, vaccines, Bacillus anthracis, Biomarker, Sugar chips
Structure type: oligomer
Location inside paper: p. 181 fig.1
Aglycon: 5-methoxycarbonylpentyl
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_146675,IEDB_146676,IEDB_150074,IEDB_225177,IEDB_885823
Methods: ELISA, serological methods
Biological activity: serological data
Comments, role: tetrasaccharide chain of the major glycoprotein of exosporium
NCBI Taxonomy refs (TaxIDs): 1392Reference(s) to other database(s): GlycomeDB:
37212
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There is only one chemically distinct structure:
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Nilsson I, Michalik D, Silipo A, Molinaro A, Vogel C
Efficient synthesis of O-antigen fragments expressed by Burkholderia anthina by modular synthesis approach
Carbohydrate Research 404 (2015)
98-107
Burkholderia anthina
(NCBI TaxID 179879,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: lung infections [ICD11:
CA4Y , ICD11:
CA4Z ];
infection due to Burkholderia [ICD11:
XN01M ]
NCBI PubMed ID: 25665786Publication DOI: 10.1016/j.carres.2014Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: christian.vogel
uni-rostock.de
Institutions: University of Rostock, Institute of Chemistry, Albert-Einstein-Strasse 3a, D-18059 Rostock, Germany, Leibniz Institute for Catalysis at the University of Rostock, Albert-Einstein-Str. 29a, D-18059 Rostock, Germany, Department of Chemical Sciences, University of Naples 'Federico II', I-80126-Via Cinthia 4, Napoli, Italy
To facilitate mapping of the interaction region of the O-chain of the lipopolysaccharide from Burkholderia anthina and of a lipopolysaccharide-specific monoclonal antibody, trisaccharide propyl α-L-rhamnopyranosyl-(1→2)-α-D-galactopyranosyl-(1→3)-α-L-rhamnopy ranoside (27) and hexasaccharide propyl α-L-rhamnopyranosyl-(1→2)-α-D-galactopyranosyl-(1→3)-α-L-rhamnopy ranosyl-(1→2)-α-L-rhamnopyranosyl-(1→2)-α-D-galactopyranosyl-(1→3)-α-L-rhamnopyranoside (33) were synthesized. These oligosaccharides represent the repeating monomer and dimer of the O-antigen, respectively.
O-antigen, Oligosaccharides, L-rhamnose, glycosylation, D-galactose, Burkholderia anthina
Structure type: polymer chemical repeating unit
Location inside paper: p.98
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130669,IEDB_133754,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, UV, glycosylation, ESI-TOF-MS
Related record ID(s): 30819, 30820
NCBI Taxonomy refs (TaxIDs): 179879Reference(s) to other database(s): GTC:G61497FY, GlycomeDB:
37265
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There is only one chemically distinct structure:
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Nilsson I, Michalik D, Silipo A, Molinaro A, Vogel C
Efficient synthesis of O-antigen fragments expressed by Burkholderia anthina by modular synthesis approach
Carbohydrate Research 404 (2015)
98-107
Burkholderia anthina
(NCBI TaxID 179879,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: lung infections [ICD11:
CA4Y , ICD11:
CA4Z ];
infection due to Burkholderia [ICD11:
XN01M ]
The structure was elucidated in this paperNCBI PubMed ID: 25665786Publication DOI: 10.1016/j.carres.2014Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: christian.vogel
uni-rostock.de
Institutions: University of Rostock, Institute of Chemistry, Albert-Einstein-Strasse 3a, D-18059 Rostock, Germany, Leibniz Institute for Catalysis at the University of Rostock, Albert-Einstein-Str. 29a, D-18059 Rostock, Germany, Department of Chemical Sciences, University of Naples 'Federico II', I-80126-Via Cinthia 4, Napoli, Italy
To facilitate mapping of the interaction region of the O-chain of the lipopolysaccharide from Burkholderia anthina and of a lipopolysaccharide-specific monoclonal antibody, trisaccharide propyl α-L-rhamnopyranosyl-(1→2)-α-D-galactopyranosyl-(1→3)-α-L-rhamnopy ranoside (27) and hexasaccharide propyl α-L-rhamnopyranosyl-(1→2)-α-D-galactopyranosyl-(1→3)-α-L-rhamnopy ranosyl-(1→2)-α-L-rhamnopyranosyl-(1→2)-α-D-galactopyranosyl-(1→3)-α-L-rhamnopyranoside (33) were synthesized. These oligosaccharides represent the repeating monomer and dimer of the O-antigen, respectively.
O-antigen, Oligosaccharides, L-rhamnose, glycosylation, D-galactose, Burkholderia anthina
Structure type: oligomer ; 537.2167 [M+Na]+
C
21H
38O
14Location inside paper: abstract, p.100, scheme 3, compound 27
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130669,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, UV, glycosylation, ESI-TOF-MS
Comments, role: repeating monomer of the O-antigen
Related record ID(s): 30644, 30820
NCBI Taxonomy refs (TaxIDs): 179879
Show glycosyltransferases
NMR conditions: in CD3OD at 293 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
1,3,2 aLRhap 103.6 72.0 72.2 73.9 69.5-70.4 18.1
1,3 aDGalp 98.0 76.3 70.7 71.6 72.3 62.7
1 aLRhap 101.2 69.5 79.1 72.5 69.5-70.4 18.21
Pr
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
1,3,2 aLRhap 5.04 3.90-4.05 3.68-3.78 3.34-3.43 3.58-3.67 1.29
1,3 aDGalp 5.01 3.90-4.05 3.90-4.05 3.90-4.05 4.19 3.68-3.78
1 aLRhap 4.71 3.90-4.05 3.68-3.78 3.49 3.58-3.67 1.29
Pr
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
1,3,2 aLRhap 103.6/5.04 72.0/3.90-4.05 72.2/3.68-3.78 73.9/3.34-3.43 69.5-70.4/3.58-3.67 18.1/1.29
1,3 aDGalp 98.0/5.01 76.3/3.90-4.05 70.7/3.90-4.05 71.6/3.90-4.05 72.3/4.19 62.7/3.68-3.78
1 aLRhap 101.2/4.71 69.5/3.90-4.05 79.1/3.68-3.78 72.5/3.49 69.5-70.4/3.58-3.67 18.21/1.29
Pr
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 1,3,2 | aLRhap | 5.04 | 3.90
4.05 | 3.68
3.78 | 3.34
3.43 | 3.58
3.67 | 1.29 |
| 1,3 | aDGalp | 5.01 | 3.90
4.05 | 3.90
4.05 | 3.90
4.05 | 4.19 | 3.68
3.78 |
| 1 | aLRhap | 4.71 | 3.90
4.05 | 3.68
3.78 | 3.49 | 3.58
3.67 | 1.29 |
| | Pr | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 1,3,2 | aLRhap | 103.6 | 72.0 | 72.2 | 73.9 | 69.5
70.4 | 18.1 |
| 1,3 | aDGalp | 98.0 | 76.3 | 70.7 | 71.6 | 72.3 | 62.7 |
| 1 | aLRhap | 101.2 | 69.5 | 79.1 | 72.5 | 69.5
70.4 | 18.21 |
| | Pr | |
|
There is only one chemically distinct structure:
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Nilsson I, Michalik D, Silipo A, Molinaro A, Vogel C
Efficient synthesis of O-antigen fragments expressed by Burkholderia anthina by modular synthesis approach
Carbohydrate Research 404 (2015)
98-107
|
a-L-Rhap-(1-2)-a-D-Galp-(1-3)-a-L-Rhap-(1-2)-a-L-Rhap-(1-2)-a-D-Galp-(1-3)-a-L-Rhap-(1-1)-Pr |
Show graphically |
Burkholderia anthina
(NCBI TaxID 179879,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: lung infections [ICD11:
CA4Y , ICD11:
CA4Z ];
infection due to Burkholderia [ICD11:
XN01M ]
The structure was elucidated in this paperNCBI PubMed ID: 25665786Publication DOI: 10.1016/j.carres.2014Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: christian.vogel
uni-rostock.de
Institutions: University of Rostock, Institute of Chemistry, Albert-Einstein-Strasse 3a, D-18059 Rostock, Germany, Leibniz Institute for Catalysis at the University of Rostock, Albert-Einstein-Str. 29a, D-18059 Rostock, Germany, Department of Chemical Sciences, University of Naples 'Federico II', I-80126-Via Cinthia 4, Napoli, Italy
To facilitate mapping of the interaction region of the O-chain of the lipopolysaccharide from Burkholderia anthina and of a lipopolysaccharide-specific monoclonal antibody, trisaccharide propyl α-L-rhamnopyranosyl-(1→2)-α-D-galactopyranosyl-(1→3)-α-L-rhamnopy ranoside (27) and hexasaccharide propyl α-L-rhamnopyranosyl-(1→2)-α-D-galactopyranosyl-(1→3)-α-L-rhamnopy ranosyl-(1→2)-α-L-rhamnopyranosyl-(1→2)-α-D-galactopyranosyl-(1→3)-α-L-rhamnopyranoside (33) were synthesized. These oligosaccharides represent the repeating monomer and dimer of the O-antigen, respectively.
O-antigen, Oligosaccharides, L-rhamnose, glycosylation, D-galactose, Burkholderia anthina
Structure type: oligomer ; 991.3838 [M+Na]+
C
39H
68O
27Location inside paper: abstract, p.100, scheme 3, compound 33
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130669,IEDB_133754,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_151528,IEDB_190606,IEDB_225177,IEDB_885823,SB_7
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, chemical synthesis, chemical methods, UV, glycosylation, ESI-TOF-MS
Comments, role: repeating dimer of the O-antigen
Related record ID(s): 30644, 30819
NCBI Taxonomy refs (TaxIDs): 179879
Show glycosyltransferases
NMR conditions: in D2O at 293 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
1,3,2,2,3,2 aLRhap 101.2 70.8 70.7 72.6 69.4 17.5
1,3,2,2,3 aDGalp 95.4-95.6 75.1 69.8 70.2 71.6 61.6
1,3,2,2 aLRhap 103.0 67.4 75.5 71.2 70.1 17.6
1,3,2 aLRhap 102.9 78.9 70.9 72.7 70.0 17.5
1,3 aDGalp 95.4-95.6 75.6 70.1 70.4 71.6 61.7
1 aLRhap 100.3 67.7 76.1 71.2 70.3 17.6
Pr
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
1,3,2,2,3,2 aLRhap 5.20 4.05-4.10 3.83-3.89 3.46 3.70-3.77 1.30
1,3,2,2,3 aDGalp 5.17 3.93 4.05-4.10 4.03 4.18-4.22 3.70-3.77
1,3,2,2 aLRhap 5.00 4.27 3.83-3.89 3.57-4.03 3.70-3.77 1.30
1,3,2 aLRhap 5.02 4.05-4.10 3.79 3.49 3.70-3.77 1.30
1,3 aDGalp 5.11 3.93 4.05-4.10 4.03 4.18-4.22 3.70-3.77
1 aLRhap 4.81 4.05-4.10 3.83-3.89 3.59 3.70-3.77 1.30
Pr
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
1,3,2,2,3,2 aLRhap 101.2/5.20 70.8/4.05-4.10 70.7/3.83-3.89 72.6/3.46 69.4/3.70-3.77 17.5/1.30
1,3,2,2,3 aDGalp 95.4-95.6/5.17 75.1/3.93 69.8/4.05-4.10 70.2/4.03 71.6/4.18-4.22 61.6/3.70-3.77
1,3,2,2 aLRhap 103.0/5.00 67.4/4.27 75.5/3.83-3.89 71.2/3.57-4.03 70.1/3.70-3.77 17.6/1.30
1,3,2 aLRhap 102.9/5.02 78.9/4.05-4.10 70.9/3.79 72.7/3.49 70.0/3.70-3.77 17.5/1.30
1,3 aDGalp 95.4-95.6/5.11 75.6/3.93 70.1/4.05-4.10 70.4/4.03 71.6/4.18-4.22 61.7/3.70-3.77
1 aLRhap 100.3/4.81 67.7/4.05-4.10 76.1/3.83-3.89 71.2/3.59 70.3/3.70-3.77 17.6/1.30
Pr
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 1,3,2,2,3,2 | aLRhap | 5.20 | 4.05
4.10 | 3.83
3.89 | 3.46 | 3.70
3.77 | 1.30 |
| 1,3,2,2,3 | aDGalp | 5.17 | 3.93 | 4.05
4.10 | 4.03 | 4.18
4.22 | 3.70
3.77 |
| 1,3,2,2 | aLRhap | 5.00 | 4.27 | 3.83
3.89 | 3.57
4.03 | 3.70
3.77 | 1.30 |
| 1,3,2 | aLRhap | 5.02 | 4.05
4.10 | 3.79 | 3.49 | 3.70
3.77 | 1.30 |
| 1,3 | aDGalp | 5.11 | 3.93 | 4.05
4.10 | 4.03 | 4.18
4.22 | 3.70
3.77 |
| 1 | aLRhap | 4.81 | 4.05
4.10 | 3.83
3.89 | 3.59 | 3.70
3.77 | 1.30 |
| | Pr | |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 1,3,2,2,3,2 | aLRhap | 101.2 | 70.8 | 70.7 | 72.6 | 69.4 | 17.5 |
| 1,3,2,2,3 | aDGalp | 95.4
95.6 | 75.1 | 69.8 | 70.2 | 71.6 | 61.6 |
| 1,3,2,2 | aLRhap | 103.0 | 67.4 | 75.5 | 71.2 | 70.1 | 17.6 |
| 1,3,2 | aLRhap | 102.9 | 78.9 | 70.9 | 72.7 | 70.0 | 17.5 |
| 1,3 | aDGalp | 95.4
95.6 | 75.6 | 70.1 | 70.4 | 71.6 | 61.7 |
| 1 | aLRhap | 100.3 | 67.7 | 76.1 | 71.2 | 70.3 | 17.6 |
| | Pr | |
|
There is only one chemically distinct structure:
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