Found 270 structures.
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1. Compound ID: 3965
|
a-D-Glcp-(1-3)-+
|
a-Abep2Ac-(1-3)-+ |
| |
-2)-a-D-Manp-(1-2)-b-D-Manp-(1-2)-b-D-Manp-(1-2)-b-D-Manp-(1-3)-a-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130701,IEDB_133966,IEDB_133967,IEDB_134618,IEDB_135513,IEDB_136104,IEDB_137340,IEDB_137485,IEDB_140116,IEDB_141807,IEDB_142488,IEDB_144983,IEDB_144995,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_152206,IEDB_153307,IEDB_1539315,IEDB_858578,IEDB_983930,IEDB_983931,SB_136,SB_192,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 1468
Knirel YA, Kocharova NA, Bystrova OV, Katzenellenbogen E, Gamian A "Structures and serology of the O-specific polysaccharides of bacteria of the genus Citrobacter" -
Archivum Immunologiae et Therapiae Experimentalis 50(6) (2002) 379-391
The review presents the structures of the O-specific polysaccharides (O-antigens) of the lipopolysaccharides isolated from over 25 Citrobacter strains, which represent different species and serogroups. The correlation between O-antigen structure and immunospecificity as well as numerous cross-reactions between Citrobacter and other enterobacterial species are discussed.
Lipopolysaccharide, structure, O-antigen, O-specific polysaccharide, serology, Citrobacter, immunospecificity
NCBI PubMed ID: 12546064Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 3707
Katzenellenbogen E, Kocharova NA, Toukach FV, Gorska S, Korzeniowska-Kowal A, Bogulska M, Gamian A, Knirel YA "Structure of an abequose-containing O-polysaccharide from Citrobacter freundii O22 strain PCM 1555" -
Carbohydrate Research 344(13) (2009) 1724-1728
The lipopolysaccharide of Citrobacter freundii O22 (strain PCM 1555) was degraded under mild acidic conditions and the O-polysaccharide released was isolated by gel chromatography. Sugar and methylation analyses along with 1H and 13C NMR spectroscopy, including two-dimensional 1H,1H ROESY and 1H,13C HMBC experiments, showed that the repeating unit of the O-polysaccharide has the following structure: where Abe is abequose (3,6-dideoxy-d-xylo-hexose). SDS-PAGE and immunoblotting revealed that the O-antigen of C. freundii O22 is serologically indistinguishable from those of Salmonella group B serovars (Typhimurium, Brandenburg, Sandiego, Paratyphi B) but not related to other abequose-containing O-antigens tested (Citrobacter werkmanii O38 and Salmonella Kentucky) or colitose (l enantiomer of abequose)-containing O-antigen of Escherichia coli O111.
Lipopolysaccharide, endotoxin, O-Specific polysaccharide structure, serological classification, Citrobacter, Citrobacter freundii
NCBI PubMed ID: 19576576Publication DOI: 10.1016/j.carres.2009.06.005Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: katzenel@iitd.pan.wroc.pl (E. Katzenellenbogen)
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation, L.Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wrocław, Poland, Department of Medical Biochemistry, Wrocław Medical University, Wrocław, Poland
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, SDS-PAGE, sugar analysis, acid hydrolysis, serological methods
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2. Compound ID: 3966
|
a-D-Glcp-(1-3)-+
|
a-Abep2Ac-(1-3)-+ |
| |
-2)-b-D-Manp-(1-2)-b-D-Manp-(1-2)-b-D-Manp-(1-2)-b-D-Manp-(1-3)-a-D-GlcpNAc-(1- |
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Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_131173,IEDB_133966,IEDB_133967,IEDB_134618,IEDB_137340,IEDB_137485,IEDB_140116,IEDB_141807,IEDB_142488,IEDB_144983,IEDB_144995,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_152206,IEDB_1539315,IEDB_173895,IEDB_76920,IEDB_858578,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_72
The structure is contained in the following publication(s):
- Article ID: 1468
Knirel YA, Kocharova NA, Bystrova OV, Katzenellenbogen E, Gamian A "Structures and serology of the O-specific polysaccharides of bacteria of the genus Citrobacter" -
Archivum Immunologiae et Therapiae Experimentalis 50(6) (2002) 379-391
The review presents the structures of the O-specific polysaccharides (O-antigens) of the lipopolysaccharides isolated from over 25 Citrobacter strains, which represent different species and serogroups. The correlation between O-antigen structure and immunospecificity as well as numerous cross-reactions between Citrobacter and other enterobacterial species are discussed.
Lipopolysaccharide, structure, O-antigen, O-specific polysaccharide, serology, Citrobacter, immunospecificity
NCBI PubMed ID: 12546064Journal NLM ID: 0114365Publisher: Basel, Boston: Birkhaüser
Correspondence: knirel@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 1778
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. III. The structure of O-antigens: A review" -
Biochemistry (Moscow) 59(12) (1994) 1325-1383
This review summarizes data on the composition and structure of the O-antigens, the polysaccharide chains of the outer-membrane lipopolysaccharides (LPS) of Gram-negative bacteria defining the immunospecificity of these microbial cells. Special reference is given to some structural features of the O-antigens, such as the presence of unique monosaccharides and noncarbohydrate components, masked regularity, and the occurrence in one microorganism of LPS with structurally different polysaccharide chains. Antigenic relationships between microorganisms belonging to different taxonomic groups are discussed.
structure, O-antigen, chemical composition, bacterial lipopolysaccharides, Salmonella livingstone C1
NCBI PubMed ID: 7533007Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 2579
Jann B, Prehm P, Jann K "Citrobacter O-antigens: Structure of the O-antigenic polysaccharide from Citrobacter sp. 396" -
Journal of Bacteriology 134 (1978) 462-469
Journal NLM ID: 2985120RPublisher: American Society for Microbiology
- Article ID: 4329
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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3. Compound ID: 6074
Structure type: oligomer
Contained glycoepitopes: IEDB_130701,IEDB_133966,IEDB_136104,IEDB_137485,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_164479,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 2708
Prinzis S, Chatterjee D, Brennan PJ "Structure and antigenicity of lipoarabinomannan from Mycobacterium bovis BCG" -
Journal of General Microbiology 139 (1993) 2649-2658
Lipoarabinomannan (LAM), a major lipoglycan of the mycobacterial cell envelope, was previously recognized as existing in two major forms: LAM with arabinofuranosyl (Araf)-containing termini (AraLAM) and a mannose-capped version (ManLAM) in which the majority of these termini are modified by additional mannose residues. Since ManLAM was first recognized in the virulent (Erdman) strain of Mycobacterium tuberculosis and the noncapped version in a rapidly growing, attenuated, H37Ra strain, it was thought that mannose capping may be a key factor in virulence. In the present study, LAM from M. bovis BCG was isolated and the non-reducing termini sequenced through differential O-alkylation, partial depolymerization and gas chromatography-mass spectrometric analyses of fragments. LAM from M. bovis BCG contains a short mannan backbone, highly branched arabinofuranosyl-containing side chains and several mannosyl residues capping the non-reducing termini of these side chains. Thus, LAM from M. bovis BCG is of the ManLAM type, showing no major structural differences at the non-reducing ends from the M. tuberculosis Erdman product. This observation led us to examine the earlier strain and to conclude that it showed little resemblance to conventional strains of M. tuberculosis. Thus, the absence of mannose caps may be more a feature of rapid growth than of avirulence. These results demonstrate that the relationship between mannose capping and disease induction is not a simple one. However, use of a panel of LAM-specific monoclonal antibodies showed antigenic differences between the BCG and the Erdman products, suggesting the presence of features specific to the different strains and pointing to LAM as a molecule within which further species and strain variations reside.
NCBI PubMed ID: 8277248Journal NLM ID: 0375371Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
Methods: 13C NMR, methylation, GC-MS, SDS-PAGE, acid hydrolysis, Western blotting, HPLC
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4. Compound ID: 6081
Structure type: oligomer
Contained glycoepitopes: IEDB_130701,IEDB_133966,IEDB_136104,IEDB_137485,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_164479,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 2708
Prinzis S, Chatterjee D, Brennan PJ "Structure and antigenicity of lipoarabinomannan from Mycobacterium bovis BCG" -
Journal of General Microbiology 139 (1993) 2649-2658
Lipoarabinomannan (LAM), a major lipoglycan of the mycobacterial cell envelope, was previously recognized as existing in two major forms: LAM with arabinofuranosyl (Araf)-containing termini (AraLAM) and a mannose-capped version (ManLAM) in which the majority of these termini are modified by additional mannose residues. Since ManLAM was first recognized in the virulent (Erdman) strain of Mycobacterium tuberculosis and the noncapped version in a rapidly growing, attenuated, H37Ra strain, it was thought that mannose capping may be a key factor in virulence. In the present study, LAM from M. bovis BCG was isolated and the non-reducing termini sequenced through differential O-alkylation, partial depolymerization and gas chromatography-mass spectrometric analyses of fragments. LAM from M. bovis BCG contains a short mannan backbone, highly branched arabinofuranosyl-containing side chains and several mannosyl residues capping the non-reducing termini of these side chains. Thus, LAM from M. bovis BCG is of the ManLAM type, showing no major structural differences at the non-reducing ends from the M. tuberculosis Erdman product. This observation led us to examine the earlier strain and to conclude that it showed little resemblance to conventional strains of M. tuberculosis. Thus, the absence of mannose caps may be more a feature of rapid growth than of avirulence. These results demonstrate that the relationship between mannose capping and disease induction is not a simple one. However, use of a panel of LAM-specific monoclonal antibodies showed antigenic differences between the BCG and the Erdman products, suggesting the presence of features specific to the different strains and pointing to LAM as a molecule within which further species and strain variations reside.
NCBI PubMed ID: 8277248Journal NLM ID: 0375371Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
Methods: 13C NMR, methylation, GC-MS, SDS-PAGE, acid hydrolysis, Western blotting, HPLC
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5. Compound ID: 6083
Structure type: oligomer
Contained glycoepitopes: IEDB_130701,IEDB_133966,IEDB_133967,IEDB_134618,IEDB_136104,IEDB_137485,IEDB_140116,IEDB_141830,IEDB_142357,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_1539315,IEDB_164479,IEDB_2278480,IEDB_858578,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 2708
Prinzis S, Chatterjee D, Brennan PJ "Structure and antigenicity of lipoarabinomannan from Mycobacterium bovis BCG" -
Journal of General Microbiology 139 (1993) 2649-2658
Lipoarabinomannan (LAM), a major lipoglycan of the mycobacterial cell envelope, was previously recognized as existing in two major forms: LAM with arabinofuranosyl (Araf)-containing termini (AraLAM) and a mannose-capped version (ManLAM) in which the majority of these termini are modified by additional mannose residues. Since ManLAM was first recognized in the virulent (Erdman) strain of Mycobacterium tuberculosis and the noncapped version in a rapidly growing, attenuated, H37Ra strain, it was thought that mannose capping may be a key factor in virulence. In the present study, LAM from M. bovis BCG was isolated and the non-reducing termini sequenced through differential O-alkylation, partial depolymerization and gas chromatography-mass spectrometric analyses of fragments. LAM from M. bovis BCG contains a short mannan backbone, highly branched arabinofuranosyl-containing side chains and several mannosyl residues capping the non-reducing termini of these side chains. Thus, LAM from M. bovis BCG is of the ManLAM type, showing no major structural differences at the non-reducing ends from the M. tuberculosis Erdman product. This observation led us to examine the earlier strain and to conclude that it showed little resemblance to conventional strains of M. tuberculosis. Thus, the absence of mannose caps may be more a feature of rapid growth than of avirulence. These results demonstrate that the relationship between mannose capping and disease induction is not a simple one. However, use of a panel of LAM-specific monoclonal antibodies showed antigenic differences between the BCG and the Erdman products, suggesting the presence of features specific to the different strains and pointing to LAM as a molecule within which further species and strain variations reside.
NCBI PubMed ID: 8277248Journal NLM ID: 0375371Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
Methods: 13C NMR, methylation, GC-MS, SDS-PAGE, acid hydrolysis, Western blotting, HPLC
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6. Compound ID: 6086
|
SUG-(1-5)-+
|
D-Manp-(1-2)-D-Manp-(1-5)-D-Araf-(1-2)-D-Araf-(1-3)-D-Araf |
Show graphically |
Structure type: oligomer
Contained glycoepitopes: IEDB_130701,IEDB_133966,IEDB_136104,IEDB_137485,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_164479,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 2708
Prinzis S, Chatterjee D, Brennan PJ "Structure and antigenicity of lipoarabinomannan from Mycobacterium bovis BCG" -
Journal of General Microbiology 139 (1993) 2649-2658
Lipoarabinomannan (LAM), a major lipoglycan of the mycobacterial cell envelope, was previously recognized as existing in two major forms: LAM with arabinofuranosyl (Araf)-containing termini (AraLAM) and a mannose-capped version (ManLAM) in which the majority of these termini are modified by additional mannose residues. Since ManLAM was first recognized in the virulent (Erdman) strain of Mycobacterium tuberculosis and the noncapped version in a rapidly growing, attenuated, H37Ra strain, it was thought that mannose capping may be a key factor in virulence. In the present study, LAM from M. bovis BCG was isolated and the non-reducing termini sequenced through differential O-alkylation, partial depolymerization and gas chromatography-mass spectrometric analyses of fragments. LAM from M. bovis BCG contains a short mannan backbone, highly branched arabinofuranosyl-containing side chains and several mannosyl residues capping the non-reducing termini of these side chains. Thus, LAM from M. bovis BCG is of the ManLAM type, showing no major structural differences at the non-reducing ends from the M. tuberculosis Erdman product. This observation led us to examine the earlier strain and to conclude that it showed little resemblance to conventional strains of M. tuberculosis. Thus, the absence of mannose caps may be more a feature of rapid growth than of avirulence. These results demonstrate that the relationship between mannose capping and disease induction is not a simple one. However, use of a panel of LAM-specific monoclonal antibodies showed antigenic differences between the BCG and the Erdman products, suggesting the presence of features specific to the different strains and pointing to LAM as a molecule within which further species and strain variations reside.
NCBI PubMed ID: 8277248Journal NLM ID: 0375371Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
Methods: 13C NMR, methylation, GC-MS, SDS-PAGE, acid hydrolysis, Western blotting, HPLC
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7. Compound ID: 6087
|
SUG-(1-3)-+
|
D-Manp-(1-2)-D-Manp-(1-5)-D-Araf-(1-2)-D-Araf-(1-5)-D-Araf |
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Structure type: oligomer
Contained glycoepitopes: IEDB_130701,IEDB_133966,IEDB_136104,IEDB_137485,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_164479,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 2708
Prinzis S, Chatterjee D, Brennan PJ "Structure and antigenicity of lipoarabinomannan from Mycobacterium bovis BCG" -
Journal of General Microbiology 139 (1993) 2649-2658
Lipoarabinomannan (LAM), a major lipoglycan of the mycobacterial cell envelope, was previously recognized as existing in two major forms: LAM with arabinofuranosyl (Araf)-containing termini (AraLAM) and a mannose-capped version (ManLAM) in which the majority of these termini are modified by additional mannose residues. Since ManLAM was first recognized in the virulent (Erdman) strain of Mycobacterium tuberculosis and the noncapped version in a rapidly growing, attenuated, H37Ra strain, it was thought that mannose capping may be a key factor in virulence. In the present study, LAM from M. bovis BCG was isolated and the non-reducing termini sequenced through differential O-alkylation, partial depolymerization and gas chromatography-mass spectrometric analyses of fragments. LAM from M. bovis BCG contains a short mannan backbone, highly branched arabinofuranosyl-containing side chains and several mannosyl residues capping the non-reducing termini of these side chains. Thus, LAM from M. bovis BCG is of the ManLAM type, showing no major structural differences at the non-reducing ends from the M. tuberculosis Erdman product. This observation led us to examine the earlier strain and to conclude that it showed little resemblance to conventional strains of M. tuberculosis. Thus, the absence of mannose caps may be more a feature of rapid growth than of avirulence. These results demonstrate that the relationship between mannose capping and disease induction is not a simple one. However, use of a panel of LAM-specific monoclonal antibodies showed antigenic differences between the BCG and the Erdman products, suggesting the presence of features specific to the different strains and pointing to LAM as a molecule within which further species and strain variations reside.
NCBI PubMed ID: 8277248Journal NLM ID: 0375371Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
Methods: 13C NMR, methylation, GC-MS, SDS-PAGE, acid hydrolysis, Western blotting, HPLC
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8. Compound ID: 6089
Structure type: oligomer
Contained glycoepitopes: IEDB_130701,IEDB_133966,IEDB_133967,IEDB_134618,IEDB_136104,IEDB_137485,IEDB_140116,IEDB_141830,IEDB_142357,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_1539315,IEDB_164479,IEDB_2278480,IEDB_858578,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 2708
Prinzis S, Chatterjee D, Brennan PJ "Structure and antigenicity of lipoarabinomannan from Mycobacterium bovis BCG" -
Journal of General Microbiology 139 (1993) 2649-2658
Lipoarabinomannan (LAM), a major lipoglycan of the mycobacterial cell envelope, was previously recognized as existing in two major forms: LAM with arabinofuranosyl (Araf)-containing termini (AraLAM) and a mannose-capped version (ManLAM) in which the majority of these termini are modified by additional mannose residues. Since ManLAM was first recognized in the virulent (Erdman) strain of Mycobacterium tuberculosis and the noncapped version in a rapidly growing, attenuated, H37Ra strain, it was thought that mannose capping may be a key factor in virulence. In the present study, LAM from M. bovis BCG was isolated and the non-reducing termini sequenced through differential O-alkylation, partial depolymerization and gas chromatography-mass spectrometric analyses of fragments. LAM from M. bovis BCG contains a short mannan backbone, highly branched arabinofuranosyl-containing side chains and several mannosyl residues capping the non-reducing termini of these side chains. Thus, LAM from M. bovis BCG is of the ManLAM type, showing no major structural differences at the non-reducing ends from the M. tuberculosis Erdman product. This observation led us to examine the earlier strain and to conclude that it showed little resemblance to conventional strains of M. tuberculosis. Thus, the absence of mannose caps may be more a feature of rapid growth than of avirulence. These results demonstrate that the relationship between mannose capping and disease induction is not a simple one. However, use of a panel of LAM-specific monoclonal antibodies showed antigenic differences between the BCG and the Erdman products, suggesting the presence of features specific to the different strains and pointing to LAM as a molecule within which further species and strain variations reside.
NCBI PubMed ID: 8277248Journal NLM ID: 0375371Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
Methods: 13C NMR, methylation, GC-MS, SDS-PAGE, acid hydrolysis, Western blotting, HPLC
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9. Compound ID: 8324
|
GalpA6NH2-(1--P--?)--+
|
Manp-(1-?)-Manp-(1-?)-Glcp-(1-?)-Manp-(1-?)-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Trivial name: core region
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_130701,IEDB_133966,IEDB_136104,IEDB_137485,IEDB_1394182,IEDB_141793,IEDB_141836,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_144998,IEDB_146664,IEDB_152206,IEDB_153219,IEDB_153220,IEDB_164174,IEDB_164479,IEDB_474450,IEDB_983930,IEDB_983931,SB_136,SB_192,SB_196,SB_197,SB_198,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 3623
Knirel YA, Kochetkov NK "The structure of lipopolysaccharides of gram-negative bacteria. II. The structure of the core region" -
Biochemistry (Moscow) 58(2) (1993) 84-99
This review summarizes data on the structure of the core of bacterial lipopolysaccharides (LPS), an oligosaccharide which binds the lipid moiety of LPS to the O-antigenic polysaccharide chain. Both S-strains with complete LPS and R-mutants having various defects of core biosynthesis are considered. The role of the core in the functioning of the outer membrane and in the manifestation of antigenic specificity of LPS is discussed.
Lipopolysaccharide, antigen, lipopolysaccharides, LPS, structure, core, bacteria, core region, region, Gram-negative bacteria, gram negative bacteria, Gram-negative, review, outer membrane, bacterial lipopolysaccharide
Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow (Russian Federation)
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10. Compound ID: 8907
|
/Variants 0/-+
|
{{{-a-D-Manp-(1-6)-}}}a-D-Manp
/Variants 0/ is:
{{{-a-D-Manp-(1-2)-}}}/n=0-?/-a-D-Manp-(1-2)-
OR (exclusively)
{{{-b-D-Manp-(1-2)-}}}Sug-(1-2)-
Sug = unassigned monosaccharide |
Show graphically |
Structure type: structural motif or average structure
Trivial name: cell-surface mannan
Contained glycoepitopes: IEDB_130701,IEDB_131173,IEDB_133966,IEDB_133967,IEDB_134618,IEDB_136104,IEDB_137485,IEDB_140116,IEDB_141793,IEDB_141795,IEDB_141828,IEDB_141829,IEDB_141830,IEDB_141831,IEDB_141832,IEDB_141833,IEDB_141834,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_1539315,IEDB_164480,IEDB_173895,IEDB_76920,IEDB_76933,IEDB_857732,IEDB_857735,IEDB_858578,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 3845
Ferreira JA, Azevedo NF, Vieira MJ, Figueiredo C, Goodfellow BJ, Monteiro MA, Coimbra MA "Identification of cell-surface mannans in a virulent Helicobacter pylori strain" -
Carbohydrate Research 345(6) (2010) 830-838
With the intent of contributing to a carbohydrate-based vaccine against the gastroduodenal pathogen, Helicobacter pylori, we report here the structure of cell-surface mannans obtained from a virulent strain. Unlike other wild-type strains, this strain was found to express in good quantities this polysaccharide in vitro. Structural analysis revealed a branched mannan formed by a backbone of α-(1→6)-linked mannopyranosyl residues with approximately 80% branching at the O-2 position. The branches were composed of O-2-linked Man residues in both α- and β-configurations: [abstract: see text]. In addition, this strain also expressed cell-surface emblematic H. pylori lipopolysaccharides (LPS) containing partially fucosylated polyLacNAc O-chains. Affinity assays with polymyxin-B and concanavalin A revealed no association between the mannan and the LPS. The described mannans may be implicated in the mediation of host-microbial interactions and immunological modulation.
Lipopolysaccharide, Helicobacter pylori, vaccine, mannan, cell-surface glycans
NCBI PubMed ID: 20227685Publication DOI: 10.1016/j.carres.2010.01.022Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: mac@ua.pt
Institutions: Departamento de Química, Universidade de Aveiro, Aveiro, Portugal, LEPAE, Department of Chemical Engineering, Faculty of Engineering, University of Porto, Porto, Portugal, Centro de Engenharia Biológica, Universidade do Minho, Campus de Gualtar, Braga, Portugal, Institute of Molecular Pathology and Immunology, University of Porto, Portugal, Medical Faculty of Porto, Porto, Portugal, CICECO, University of Aveiro, Aveiro, Portugal, Department of Chemistry, University of Guelph, Guelph, ON, Canada
Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR, composition analysis, affinity chromatography
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11. Compound ID: 9999
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L-Rhap-(1-2)-D-Manp-(1-2)-D-Manp-(1-6)-+
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-3)-L-Rhap-(1-3)-D-Galp-(1-3)-D-Galp-(1-3)-b-D-Galf-(1- |
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Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_115013,IEDB_130645,IEDB_130701,IEDB_133966,IEDB_136044,IEDB_136095,IEDB_136104,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_149558,IEDB_151528,IEDB_152206,IEDB_164479,IEDB_190606,IEDB_225177,IEDB_742246,IEDB_885823,IEDB_918313,IEDB_918314,IEDB_983930,SB_136,SB_165,SB_166,SB_187,SB_195,SB_196,SB_44,SB_67,SB_7,SB_72,SB_87,SB_88
The structure is contained in the following publication(s):
- Article ID: 4168
Takeuchi M, Yokota A, Misaki A "Comparative structures of the cell-wall polysaccharides of four species of the genus Microbacterium" -
Journal of General and Applied Microbiology 36 (1990) 255-271
Cell-wall polysaccharides purified from four species of the genus Microbacterium were characterized in relation to their taxonomy, based on 1H-NMR and 13C-NMR spectrometry, methylation analysis and Smith degradation. The polysaccharide isolated from M. imperiale IFO 12610 contained a backbone consisting of heptasaccharide repeating-units, to which side chains of L-rhamnopyranosyl-(1→2)-D-mannopyranosyl-(1→2)-D-mannopyranoses as branches were attached to position 6 of the 3-linked D-galactopyranose residues. The polysaccharide of M. lacticum IFO 14135 contained hexasaccharide repeating-units, to which disaccharide groups of L-rhamnopyranosyl-(1→2)-L-rhamnopyranoses were attached to position 6 of the 3-linked D-galactopyranose residues to form branches. The polysaccharide of M. arborescens IFO 3750 consists of pentasaccharide repeating-units, and single D-mannopyranosyl groups were attached as branches to position 6 of the 3-linked D-galactofuranose residues. The polysaccharide of M. laevaniformans IFO 14471 had a more complicated structure consisting of decasaccharide repeating-units, and branches occur at three different positions. Thus, the cell-wall polysaccharides of the former three species were similar in their basic structures, but that of M. laevaniformans has a significantly different structure. These results indicated that the structures of cell-wall polysaccharides are heterogeneous in the genus Microbacterium and may characterize the species in the genus.
Journal NLM ID: 0165543Publisher: Tokyo: Microbiology Research Foundation
Institutions: Institute for Fermentation, Osaka, Japan, Faculty of Science of Living, Osaka City University, Osaka, Japan
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, gel filtration, IR, partial acid hydrolysis, Smith degradation, HPLC
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12. Compound ID: 10107
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D-Araf-(1-5)-D-Araf-(1-2)-/Variants 0/-+ D-Manp-(1-2)-D-Manp-(1-6)-+
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-5)-D-Araf-(1-5)-D-Araf-(1-5)-D-Araf-(1-5)-D-Araf-(1-4)-D-Galp-(1-5)-D-Galf-(1-5)-D-Araf-(1-5)-D-Araf-(1-
/Variants 0/ is:
D-Araf-(1-3)-
OR (exclusively)
D-Araf-(1-2)- |
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Structure type: polymer chemical repeating unit
Trivial name: arabinogalactomannan
Contained glycoepitopes: IEDB_130701,IEDB_133966,IEDB_136044,IEDB_136095,IEDB_136104,IEDB_136906,IEDB_137472,IEDB_137485,IEDB_141794,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_151528,IEDB_152206,IEDB_164479,IEDB_190606,IEDB_983930,SB_136,SB_165,SB_166,SB_187,SB_195,SB_196,SB_44,SB_67,SB_7,SB_72,SB_88
The structure is contained in the following publication(s):
- Article ID: 4197
Abou-Zeid C, Voiland A, Michel G, Cocito C "Structure of the wall polysaccharide isolated from a group of corynebacteria" -
European Journal of Biochemistry 128 (1982) 363-370
Leprosy-derived corynebacteria or LDC is a group of ‘diphtheroid’ bacteria isolated from leprosy patients. Their cell wall was previously shown to contain, in addition to a peptidoglycan of the meso-diaminopimelic type and to mycolic acids of the corynomycolic type, a polysaccharide fraction. The present work relates the preparation and analysis of the wall polysaccharides of three LDC strains and two reference organisms Mycobacterium smegmatis and Corynebacterium hoffmannii. These polymers were obtained by mild alkali hydrolysis of purified cell walls, and were purified to homogeneity by column chromatography on DEAE-cellulose and Sephadex G-75 columns. By this procedure, two fractions containing, respectively, neutral polysaccharides and polysaccharide-peptidoglycan complexes, were obtained. The former, which was composed of arabinose and galactose in M. smegmatis, contained, in addition, mannose in LDC cells, and mannose plus glucose in C. hoffmannii. The presence of arabinose, galactose and mannose in a constant ratio in the wall polysaccharide preparations of three LDC isolates suggests that arabinogalactomannan is the polysaccharide component of the envelope of this group of corynebacteria. A structural analysis was accomplished by methylation analysis and periodate oxidation. On the basis of the analytical data, a model for the primary structure of the polymer has been proposed, which is similar to that available for the arabinogalactan of Mycobacterium tuberculosis. According to the proposed model, the main chain of LDC polysaccharide is made of galactopyranose, galactofuranose and arabinofuranose. The latter is present in both the branching points and the lateral chains of the polymer. Mannose in the pyranose form, and arabinose in the furanose form, are located at the extremities. In conclusion, the inference that arabinogalactan is the wall polysaccharide of microorganisms belonging to genera Corynebacterium, Mycobacterium, Nocardia (CMN group) is not generally valid, since the corresponding polymers in some corynebacteria have additional monosaccharide components.
NCBI PubMed ID: 6759115Publication DOI: 10.1111/j.1432-1033.1982.tb06973.xJournal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Microbiology and Genetics, Institute of Cell Pathology, University of Louvain Medical School, Brussels, Laboratoire de Biochimie Microbienne, Université de Lyon I, Vieurbanne
Methods: GC-MS, TLC, acid hydrolysis, GC, paper chromatography, enzymatic digestion
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13. Compound ID: 10467
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-2)-D-Manp-(1-2)-D-Manp-(1-2)-D-Manp-(1-3)-D-Manp-(1-3)-D-Manp-(1- |
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Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_115576,IEDB_130701,IEDB_131173,IEDB_133966,IEDB_133967,IEDB_134618,IEDB_136104,IEDB_137485,IEDB_140116,IEDB_141111,IEDB_141795,IEDB_141830,IEDB_142357,IEDB_143632,IEDB_144983,IEDB_144994,IEDB_144995,IEDB_152206,IEDB_153756,IEDB_1539315,IEDB_164174,IEDB_164175,IEDB_164176,IEDB_164177,IEDB_164479,IEDB_164480,IEDB_173895,IEDB_174840,IEDB_2278480,IEDB_241100,IEDB_76920,IEDB_76933,IEDB_858578,IEDB_983930,SB_136,SB_196,SB_197,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 4329
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
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14. Compound ID: 15250
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a-D-Manp-(1-6)-+
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D-Manp-(1-2)-D-Manp-(1-2)-a-D-Manp-(1-3)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc |
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Structure type: structural motif or average structure
Compound class: N-glycan
Contained glycoepitopes: IEDB_123886,IEDB_130701,IEDB_133966,IEDB_135813,IEDB_136104,IEDB_137340,IEDB_137485,IEDB_140116,IEDB_141793,IEDB_141807,IEDB_141830,IEDB_142357,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_151531,IEDB_152206,IEDB_153212,IEDB_1539315,IEDB_164479,IEDB_2278480,IEDB_540671,IEDB_548907,IEDB_983930,SB_136,SB_196,SB_197,SB_198,SB_33,SB_44,SB_67,SB_72,SB_73,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 5927
Flores MS, Obregon-Cardenas A, Rangel R, Tamez E, Flores A, Trejio-Avila L, Quinterto I, Arevalo K, Maldonado MG, Gandarilla FL, Galan L "Glycan moieties in Entamoeba histolytica ubiquitin are immunodominant" -
Parasite Immunology 43(4) (2021) e12812
The ubiquitin-proteasome system plays a central role performing several functions to maintain parasite homeostasis. We have reported the partial characterization of N-linked glycosylation profile in E. histolytica ubiquitin (EhUb). Here we examined the immunogenicity and antigenicity of carbohydrates in EhUbiquitin. Rabbits were immunized with purified EhUbiquitin or purified recombinant rUb expressed by E. coli. Using Western Blot, we explored the immunogenicity and antigenicity of protein portion and carbohydrates moiety. Interestingly, immunized rabbits produced antibodies to both Ub glycoprotein and rUb; but antibodies against carbohydrates were immunodominant, rather than antibodies to the protein moiety of EhUbiquitin. In addition, we observed that antibodies to protein moiety are not conserved in serum unless antigen is continually administrated. Conversely, anti-Ub glycoprotein antibodies are well maintained in circulation. In humans, infection with Entamoeba histolytica induces strong IgG anti-Ub response. The human antibodies recognize both, the protein moieties and the glycosylated structure. Entamoeba histolytica ubiquitin is immunogenic and antigenic. The glycan moieties are immunodominant and induces IgG. These data open the door to use carbohydrates as potential targets for diagnose tests, drugs and vaccine to prevent this parasitic disease.
antigen, polysaccharides, immunogen, glycans, Entamoeba histolytica, N-linked glycosylation, EhUbiquitin, Ubiquitin
Publication DOI: 10.1111/pim.12812Journal NLM ID: 7910948Publisher: Oxford: Wiley
Institutions: Facultad de Ciencias Biologicas, Instituto de Biotecnologia. San Nicolas de los Garza, Universidad Autonoma de Nuevo Leon, Nuevo Leon, Mexico maria.floresgz@uanl.edu.mx, floresgms@yahoo.com
Methods: PCR, ELISA, Western blotting, genetic methods, immunization
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15. Compound ID: 15505
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a-D-Manp-(1-6)-+
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D-Manp-(1-2)-D-Manp-(1-2)-a-D-Manp-(1-3)-b-D-Manp-(1-4)-b-D-GlcpNAc-(1-4)-b-D-GlcpNAc |
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Structure type: structural motif or average structure
; 1580 [M+Na]+
Compound class: N-glycan
Contained glycoepitopes: IEDB_123886,IEDB_130701,IEDB_133966,IEDB_135813,IEDB_136104,IEDB_137340,IEDB_137485,IEDB_140116,IEDB_141793,IEDB_141807,IEDB_141830,IEDB_142357,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_151531,IEDB_152206,IEDB_153212,IEDB_1539315,IEDB_164479,IEDB_2278480,IEDB_540671,IEDB_548907,IEDB_983930,SB_136,SB_196,SB_197,SB_198,SB_33,SB_44,SB_67,SB_72,SB_73,SB_74,SB_85
The structure is contained in the following publication(s):
- Article ID: 5986
Obregón A, Flores MS, Rangel R, Arevalo K, Maldonado G, Quinterto I, Galan L "Characterization of N-glycosylations in Entamoeba histolytica ubiquitin" -
Experimental Parasitology 196 (2019) 38-47
Entamoeba histolytica harbors an extensive intracellular distribution of ubiquitin-proteasome systems important for numerous cellular processes. However, glycosylation studies of ubiquitin-proteasome components have not yet been elucidated. Here we report the partial characterization of N-linked glycosylation profile in E. histolytica ubiquitin by Fluorophore-Assisted Carbohydrate Electrophoresis (FACE), Nanoelectrospray Ionization-Tandem Mass Spectrometry (NSI-MS), Matrix-Assisted Laser-Desorption time-of-flight Mass Spectrometry (MALDI-TOF MS) and Gas Chromatography-Mass Spectrometry (GC-MS) analysis. To our knowledge, the data presented in this report represents the first structural glycomics analysis of E. histolytica ubiquitin, while most of the reports are performed on whole parasitic glycan profiles. The glycan profile of E. histolytica ubiquitin has high mannose N-glycan structures. The N-linked glycan profile showed fragments from Hex3HexNAc2 to Hex9HexNAc2. Based in our findings and ubiquitin function, we hypothesize that the same ubiquitin Asn-Asp-Ser sequon carries heterogenic glycosylations, at different metabolic pathway stages according to ubiquitin functional requirements. Finally, we propose a set of possible high mannose N-glycan structures that will help to elucidate the ubiquitin biochemical composition and may well represent good targets for anti-amoebic drugs.
MALDI-TOF MS, Entamoeba histolytica, N-glycosylation, GC-MS, N-glycans, Ubiquitin, Continuous elution electrophoresis, NSI-MS/MS
NCBI PubMed ID: 30444974Publication DOI: 10.1016/j.exppara.2018.11.003Journal NLM ID: 0370713Publisher: Orlando, FL : Academic Press
Correspondence: Maria S. Flores
;
Institutions: Universidad Autónoma de Nuevo León, Facultad de Ciencias Biológicas, Instituto de Biotecnología, San Nicolás de los Garza, Nuevo León, Mexico, Department of Head and Neck Surgery, University of Texas MD Anderson Cancer Center, Houston, Texas, USA
Methods: GC-MS, SDS-PAGE, MALDI-TOF MS, nESI-CID-MS, FACE, enzymatic digestion, permethylation, hydrazinolysis, nESI-MS/MS
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