Found 83 structures.
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1. Compound ID: 487
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Contained glycoepitopes: IEDB_130648,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_885822
The structure is contained in the following publication(s):
- Article ID: 152
Varbanets L, Moskalenko N, Knirel Y, Kocharova N, Muras V, Chitchevitch N "Studies on the structure and activity of Burkholderia solanacearum lipopolysaccharides" -
Book: Pseudomonas Syringae Pathovars and Related Pathogens (series: Developments in Plant Pathology) (1997) 484-489
Lipopolysaccharides (LPS) were isolated using the phenol-water procedure from 25 strains of Burkholderia (formerly Pseudomonas) solanacearum, belonging to biovars I-IV. Structures of O-specific polysaccharides (0-PS) were elucidated, using methylation analysis and NMR spectroscopy, including a computer-assisted 13C NMR-based analysis. Six distinct but related polysaccharide structures were identified. They have a backbone which consists of three L-rhamnopyranose residues and one residue of 2-acetamido-2-deoxy-D-glucopyranose and in some strains is substituted by a residue of L-xylopyranose or L-rhamnopyranose as a side chain. The 0-PS of most strains are not strictly regular and contain at least two types of structurally different oligosaccharide repeating units. Serological studies, using ELISA, revealed cross-reactivity between LPS of most of B. solanacearum strains investigated, thus indicating the occurrence of common antigenic determinants. At the same time, some antigenic differences were observed for LPS with structurally similar 0-PS chains which may be due to the presence of nonidentified minor components. The LPS showed a wide spectrum of pharmacological effects. It was found that LPS was able to extend the life of mice with experimental lymphoid and lymphocytic leukemia. B. solanacearum LPS expressed a broad antimetastatic effect. This was shown in a decrease of both volume and amount of metastases (for about 40 and 5 times, respectively) in mice with Lewis lung carcinoma. In mice with melanoma B-16 a lower level of LPS antimetastatic activity was found. We assume that in spite of the damage which 8. solanacearum induces in some agricultural plants its LPS may exert a pronounced positive action exhibiting antileukosic and antimetastatic effects.
Lipopolysaccharide, lipopolysaccharides, LPS, structure, Burkholderia, Pseudomonas, chain, group, O-polysaccharide, activity, Burkholderia solanacearum, pathogen, pathogens, pathovar, Pseudomonas solanacearum, Pseudomonas syringae
Publication DOI: 10.1007/978-94-011-5472-7_87Publisher: Springer Netherlands
Editors: Rudolph K, Burr TJ, Mansfield JW, Stead D, Vivian A, von Kietzell J
Institutions: D.K.Zabolotny Institute of Microbiology and Virology, NAS of Ukraine, Zabolotnogo 154, Kiev Ukraine, N.D.Zelinsky Institute of Organic Chemistry,Russian Academy of Sciences,Leninsky Prospekt 47, Moscow, Russian Federation.
Methods: NMR, ELISA, GPC, phenol-water extraction
- Article ID: 404
Varbanets LD, Moskalenko NV, Kavun EM, Muras VA, Zhitkevich NV "Antigenic activity of Burkholderia solanacearum lipopolysaccharides" -
Biochemistry (Moscow) 61(5) (1996) 835-841
The interaction of the antiserum against Burkholderia solanacearum ICMP 8110 cells with lipopolysaccharides from 19 strains of B. solanacearum differing in O-polysaccharide structure has been studied using ELISA. No corellation was found between the O-polysaccharide structure and serological activity of the lipopolysaccharide. Most of lipopolysaccharides isolate from . B. solanacearum strains (exept for 4157, 767, and 7942) displayed cross-reactivity with the tested antiserum. These data indicate that the strains under study pertains to the same serogroup. It can not be excluded that some nonidentified components in the O-polysaccharide structure are responsible for the serological activity of the lipopolysaccharide.
lipopolysaccharides, Burkholderia, O-specific polysaccharide, activity, Burkholderia solanacearum, antigenic
NCBI PubMed ID: 8754270Journal NLM ID: 0376536Publisher: Nauka/Interperiodica
Institutions: DK Zabilotny Institute of Microbiology and Virologi, National Academy of Science of Ukraine, 252143 Kiev, ul Zabolotnogo, 154, AV Palladine Institute of Biochemistry, National Academy of Science of Ukraine, Kiev, Ukraine
Methods: ELISA
- Article ID: 1453
Corsaro MM, De Castro C, Molinaro A, Parrilli M "Structure of lipopolysaccharides from phytopathogenic Gram-negative bacteria" -
Book: Recent Research Developments in Phytochemistry (2001) Vol. 5, 119-138
This review collects the structural data of lipopolysaccharide components arising from all phytopathogenic bacteria so far investigated. The structural approaches and the main biological role of these macromolecules are also reported.
Lipopolysaccharide, lipopolysaccharides, structure, core, lipid A, O-polysaccharide, gram negative bacteria
WWW link: https://books.google.ru/books/about/Recent_Research_Developments_in_Phytoche.html?id=5CJacgAACAAJ&redir_esc=yPublisher: Research Signpost, Trivandrum, India
Editors: Pandalai SG
Institutions: Dipartimento di Chimica Organica e Biochimica, Complesso Universitario Monte S.Angelo Via Cintia, 4, 80126 Napoli, Italy
- 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: 2209
Kocharova NA, Knirel YA, Shashkov AS, Kochetkov NK, Varbanets LD "The structure of O-specific polysaccharide from Pseudomonas solanacearum ICMP 4157" -
Carbohydrate Research 228 (1992) 315-320
No abstract available
NCBI PubMed ID: 1381280Publication DOI: 10.1016/s0008-6215(00)90569-xJournal NLM ID: 0043535Publisher: Elsevier
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences of the U.S.S.R., Moscow
Methods: 13C NMR, 1H NMR, NMR-2D, sugar analysis, acid hydrolysis, Smith degradation, GPC
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2. Compound ID: 1011
Structure type: oligomer
Trivial name: phospholipid (glycosylphosphopolyprenol)
The structure is contained in the following publication(s):
- Article ID: 303
Lee RE, Brennan PJ, Besra GS "Mycobacterium tuberculosis cell envelope" -
Book: Tuberculosis (series: Current Topics in Microbiology and Immunology) (1996) Vol. 215, 1-27
The mycobacterial cell wall is a complex and intriguing mixture of components which sets Mycobacterium tuberculosis apart from all other known bacterial species (Goodfellow and Minnikin 1984). To understand the M. tuberculosis cell wall, one must first consider the biology of the tubercle bacillus. Tuberculosis has long been known as a cause of morbidity and mortality worldwide. Indeed it is believed that one third of the word’s population is infected with M. tuberculosis (Sudre et al. 1992). Evidence of tuberculosis-like infections date back many thousands of years, and it is very likely that tuberculosis-related infections have plagued humankind since the dawn of civilization. M. tuberculosis is primarily an intracellular pathogen which resides within the phagolysosomes of alveolar macrophages. Perhaps as a consequence of this intracellular environment, the highly intricate features of the tubercle bacilli cell wall have undergone extensive evolutionary changes.
lipid, Mycobacteria, membrane, arabinogalactan, cell envelope, lipoarabinomannan, Mycobacterium tuberculosis, peptidoglycan
Publication DOI: 10.1007/978-3-642-80166-2_1Publisher: Berlin, Heidelberg: Springer.
Editors: Shinnick TM
Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO, 80523, USA
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3. Compound ID: 1012
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b-D-Araf-(1-2)-a-D-Araf-(1-5)-+
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b-D-Araf-(1-2)-a-D-Araf-(1-3)-a-D-Araf-(1-5)-a-D-Araf |
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Structure type: fragment of a bigger structure
Trivial name: nonreducing terminal epitope of lipoarabinomannan
Contained glycoepitopes: IEDB_1309625,IEDB_134619,IEDB_857717,IEDB_857718
The structure is contained in the following publication(s):
- Article ID: 303
Lee RE, Brennan PJ, Besra GS "Mycobacterium tuberculosis cell envelope" -
Book: Tuberculosis (series: Current Topics in Microbiology and Immunology) (1996) Vol. 215, 1-27
The mycobacterial cell wall is a complex and intriguing mixture of components which sets Mycobacterium tuberculosis apart from all other known bacterial species (Goodfellow and Minnikin 1984). To understand the M. tuberculosis cell wall, one must first consider the biology of the tubercle bacillus. Tuberculosis has long been known as a cause of morbidity and mortality worldwide. Indeed it is believed that one third of the word’s population is infected with M. tuberculosis (Sudre et al. 1992). Evidence of tuberculosis-like infections date back many thousands of years, and it is very likely that tuberculosis-related infections have plagued humankind since the dawn of civilization. M. tuberculosis is primarily an intracellular pathogen which resides within the phagolysosomes of alveolar macrophages. Perhaps as a consequence of this intracellular environment, the highly intricate features of the tubercle bacilli cell wall have undergone extensive evolutionary changes.
lipid, Mycobacteria, membrane, arabinogalactan, cell envelope, lipoarabinomannan, Mycobacterium tuberculosis, peptidoglycan
Publication DOI: 10.1007/978-3-642-80166-2_1Publisher: Berlin, Heidelberg: Springer.
Editors: Shinnick TM
Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO, 80523, USA
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4. Compound ID: 1014
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a-D-Manp-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-3)-+
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a-D-Manp-(1-2)-a-D-Manp-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-a-D-Araf |
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Structure type: fragment of a bigger structure
Trivial name: nonreducing terminal epitope of lipoarabinomannan
Contained glycoepitopes: IEDB_130701,IEDB_1309625,IEDB_134619,IEDB_136104,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_857717,IEDB_857718,IEDB_857722,IEDB_857723,IEDB_857726,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 303
Lee RE, Brennan PJ, Besra GS "Mycobacterium tuberculosis cell envelope" -
Book: Tuberculosis (series: Current Topics in Microbiology and Immunology) (1996) Vol. 215, 1-27
The mycobacterial cell wall is a complex and intriguing mixture of components which sets Mycobacterium tuberculosis apart from all other known bacterial species (Goodfellow and Minnikin 1984). To understand the M. tuberculosis cell wall, one must first consider the biology of the tubercle bacillus. Tuberculosis has long been known as a cause of morbidity and mortality worldwide. Indeed it is believed that one third of the word’s population is infected with M. tuberculosis (Sudre et al. 1992). Evidence of tuberculosis-like infections date back many thousands of years, and it is very likely that tuberculosis-related infections have plagued humankind since the dawn of civilization. M. tuberculosis is primarily an intracellular pathogen which resides within the phagolysosomes of alveolar macrophages. Perhaps as a consequence of this intracellular environment, the highly intricate features of the tubercle bacilli cell wall have undergone extensive evolutionary changes.
lipid, Mycobacteria, membrane, arabinogalactan, cell envelope, lipoarabinomannan, Mycobacterium tuberculosis, peptidoglycan
Publication DOI: 10.1007/978-3-642-80166-2_1Publisher: Berlin, Heidelberg: Springer.
Editors: Shinnick TM
Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO, 80523, USA
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5. Compound ID: 1015
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a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Manp-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-a-D-Araf |
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Structure type: fragment of a bigger structure
Trivial name: nonreducing terminal epitope of lipoarabinomannan
Contained glycoepitopes: IEDB_130701,IEDB_1309625,IEDB_136104,IEDB_140116,IEDB_141830,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_857718,IEDB_857722,IEDB_857726,IEDB_857728,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 303
Lee RE, Brennan PJ, Besra GS "Mycobacterium tuberculosis cell envelope" -
Book: Tuberculosis (series: Current Topics in Microbiology and Immunology) (1996) Vol. 215, 1-27
The mycobacterial cell wall is a complex and intriguing mixture of components which sets Mycobacterium tuberculosis apart from all other known bacterial species (Goodfellow and Minnikin 1984). To understand the M. tuberculosis cell wall, one must first consider the biology of the tubercle bacillus. Tuberculosis has long been known as a cause of morbidity and mortality worldwide. Indeed it is believed that one third of the word’s population is infected with M. tuberculosis (Sudre et al. 1992). Evidence of tuberculosis-like infections date back many thousands of years, and it is very likely that tuberculosis-related infections have plagued humankind since the dawn of civilization. M. tuberculosis is primarily an intracellular pathogen which resides within the phagolysosomes of alveolar macrophages. Perhaps as a consequence of this intracellular environment, the highly intricate features of the tubercle bacilli cell wall have undergone extensive evolutionary changes.
lipid, Mycobacteria, membrane, arabinogalactan, cell envelope, lipoarabinomannan, Mycobacterium tuberculosis, peptidoglycan
Publication DOI: 10.1007/978-3-642-80166-2_1Publisher: Berlin, Heidelberg: Springer.
Editors: Shinnick TM
Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO, 80523, USA
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6. Compound ID: 1578
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{{{-a-D-Manp-(1-2)-}}}/n=0-2/-a-D-Manp-(1-5)-b-D-Araf-(1--/(->5) arabinan/ |
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Structure type: fragment of a bigger structure
Aglycon: (->5) arabinan
Trivial name: mannooligosaccharide cap of the LAM (ManLAM)
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141795,IEDB_141830,IEDB_141834,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_164480,IEDB_76933,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 492
Nigou J, Gilleron M, Brando T, Puzo G "Structural analysis of mycobacterial lipoglycans" -
Applied Biochemistry and Biotechnology 118(1-3) (2004) 253-267
Mycobacterium tuberculosis, the causative agent of tuberculosis, is one of the most effective human pathogens. The mycobacterial cell envelope contains lipoglycans, and of particular interest is lipoarabinomannan (LAM), one of the most potent mycobacterial immunomodulatory molecules. The importance of lipoarabinomannan (LAM) in the immunopathogenesis of tuberculosis has incited structural studies on this molecule to (1) establish a precise structural model of the molecule and (2) decipher the structure/function relationships. In recent years, we have focused on the two domains essential for LAM biologic activities: the mannosyl-phosphatidyl-myo-inositol anchor and the caps. We review here the recent procedures developed for the structural analysis of these domains
structure, Mycobacterium, lipoarabinomannan, capillary electrophoresis, lipoglycan, nuclear magnetic resonance.
NCBI PubMed ID: 15304754Publication DOI: 10.1385/abab:118:1-3:253Journal NLM ID: 8208561Publisher: Humana Press
Correspondence: jerome.nigou@ipbs.fr
Institutions: Department of Molecular Mechanisms of Mycobacterial Infections, Institut de Pharmacologie et de Biologie Structurale, CNRS UMR 5089, 205, Route de Narbonne, 31077 Toulouse Cedex 4, France
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7. Compound ID: 1579
Structure type: fragment of a bigger structure
Aglycon: (->5) arabinan
Trivial name: phospho-myo-inositol cap (PILAM)
The structure is contained in the following publication(s):
- Article ID: 492
Nigou J, Gilleron M, Brando T, Puzo G "Structural analysis of mycobacterial lipoglycans" -
Applied Biochemistry and Biotechnology 118(1-3) (2004) 253-267
Mycobacterium tuberculosis, the causative agent of tuberculosis, is one of the most effective human pathogens. The mycobacterial cell envelope contains lipoglycans, and of particular interest is lipoarabinomannan (LAM), one of the most potent mycobacterial immunomodulatory molecules. The importance of lipoarabinomannan (LAM) in the immunopathogenesis of tuberculosis has incited structural studies on this molecule to (1) establish a precise structural model of the molecule and (2) decipher the structure/function relationships. In recent years, we have focused on the two domains essential for LAM biologic activities: the mannosyl-phosphatidyl-myo-inositol anchor and the caps. We review here the recent procedures developed for the structural analysis of these domains
structure, Mycobacterium, lipoarabinomannan, capillary electrophoresis, lipoglycan, nuclear magnetic resonance.
NCBI PubMed ID: 15304754Publication DOI: 10.1385/abab:118:1-3:253Journal NLM ID: 8208561Publisher: Humana Press
Correspondence: jerome.nigou@ipbs.fr
Institutions: Department of Molecular Mechanisms of Mycobacterial Infections, Institut de Pharmacologie et de Biologie Structurale, CNRS UMR 5089, 205, Route de Narbonne, 31077 Toulouse Cedex 4, France
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8. Compound ID: 2253
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a-D-Manp-(1-2)-a-D-Manp-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-+
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a-D-Manp-(1-2)-a-D-Manp-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-3)-a-D-Araf-(1-5)-a-D-Araf-(1--/polymer of -5)aDAraf(1-/ |
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Structure type: oligomer
Aglycon: polymer of -5)aDAraf(1-
Trivial name: lipoarabinomannan
Contained glycoepitopes: IEDB_130701,IEDB_1309625,IEDB_134619,IEDB_136104,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_857717,IEDB_857718,IEDB_857722,IEDB_857723,IEDB_857726,IEDB_857727,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 743
Khoo KH, Tang JB, Chatterjee D "Variation in mannose-capped terminal arabinan motifs of lipoarabinomannans from clinical isolates of Mycobacterium tuberculosis and Mycobacterium avium complex" -
Journal of Biological Chemistry 276(6) (2001) 3863-3871
The unique terminal arabinan motifs of mycobacterial lipoarabinomannan (LAM), which are mannose-capped to different extents, probably constitute the single most important structural entity engaged in receptor binding and subsequent immunopathogenesis. We have developed a concerted approach of endoarabinanase digestion coupled with chromatography and mass spectrometry analysis to rapidly identify and quantitatively map the complement of such terminal units among the clinical isolates of different virulence and drug resistance profiles. In comparison with LAM from laboratory strains of Mycobacterium tuberculosis, an ethambutol (Emb) resistant clinical isolate was shown to have a significantly higher proportion of nonmannose capped arabinan termini. More drastically, the mannose capping was completely inhibited when an Emb-susceptible strain was grown in the presence of subminimal inhibitory concentration of Emb. Both cases resulted in an increase of arabinose to mannose ratio in the overall glycosyl composition of LAM. Emb, therefore, not only could affect the complete elaboration of the arabinan as found previously for LAM from Mycobacterium smegmatis resistant mutant but also could inhibit the extent of mannose capping and hence its associated biological functions in M. tuberculosis. Unexpectedly, an intrinsically Emb-resistant Mycobacterium avium isolate of smooth transparent colony morphology was found to have most of its arabinan termini capped with a single mannose residue instead of the more common dimannoside as established for LAM from M. tuberculosis. This is the first report on the LAM structure from M. avium complex, an increasingly important opportunistic infectious agent afflicting AIDS patients
structure, virulence, lipoarabinomannan, Mycobacterium tuberculosis, tuberculosis, Mycobacterium avium Complex
NCBI PubMed ID: 11073941Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: delphi@lamar.colostate.edu
Institutions: Department of Microbiology, Colorado State University, Fort Collins, Colorado 80523, USA
Methods: HPAEC, MS, enzymatic digestion
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9. Compound ID: 2254
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a-D-Manp-(1-2)-a-D-Manp-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-a-D-Araf-(1--/polymer of -5)aDAraf(1-/ |
Show graphically |
Structure type: oligomer
Aglycon: polymer of -5)aDAraf(1-
Trivial name: lipoarabinomannan
Contained glycoepitopes: IEDB_130701,IEDB_1309625,IEDB_136104,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_857718,IEDB_857722,IEDB_857726,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 743
Khoo KH, Tang JB, Chatterjee D "Variation in mannose-capped terminal arabinan motifs of lipoarabinomannans from clinical isolates of Mycobacterium tuberculosis and Mycobacterium avium complex" -
Journal of Biological Chemistry 276(6) (2001) 3863-3871
The unique terminal arabinan motifs of mycobacterial lipoarabinomannan (LAM), which are mannose-capped to different extents, probably constitute the single most important structural entity engaged in receptor binding and subsequent immunopathogenesis. We have developed a concerted approach of endoarabinanase digestion coupled with chromatography and mass spectrometry analysis to rapidly identify and quantitatively map the complement of such terminal units among the clinical isolates of different virulence and drug resistance profiles. In comparison with LAM from laboratory strains of Mycobacterium tuberculosis, an ethambutol (Emb) resistant clinical isolate was shown to have a significantly higher proportion of nonmannose capped arabinan termini. More drastically, the mannose capping was completely inhibited when an Emb-susceptible strain was grown in the presence of subminimal inhibitory concentration of Emb. Both cases resulted in an increase of arabinose to mannose ratio in the overall glycosyl composition of LAM. Emb, therefore, not only could affect the complete elaboration of the arabinan as found previously for LAM from Mycobacterium smegmatis resistant mutant but also could inhibit the extent of mannose capping and hence its associated biological functions in M. tuberculosis. Unexpectedly, an intrinsically Emb-resistant Mycobacterium avium isolate of smooth transparent colony morphology was found to have most of its arabinan termini capped with a single mannose residue instead of the more common dimannoside as established for LAM from M. tuberculosis. This is the first report on the LAM structure from M. avium complex, an increasingly important opportunistic infectious agent afflicting AIDS patients
structure, virulence, lipoarabinomannan, Mycobacterium tuberculosis, tuberculosis, Mycobacterium avium Complex
NCBI PubMed ID: 11073941Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: delphi@lamar.colostate.edu
Institutions: Department of Microbiology, Colorado State University, Fort Collins, Colorado 80523, USA
Methods: HPAEC, MS, enzymatic digestion
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10. Compound ID: 3741
Structure type: polymer chemical repeating unit
Trivial name: LAM
The structure is contained in the following publication(s):
- Article ID: 698
Guerardel Y, Maes E, Elass E, Leroy Y, Timmerman P, Besra GS, Locht C, Strecker G, Kremer L "Structural study of lipomannan and lipoarabinomannan from Mycobacterium chelonae. Presence of unusual components with α1,3-mannopyranose side chains" -
Journal of Biological Chemistry 277(34) (2002) 30635-30648
Lipomannan (LM) and lipoarabinomannan (LAM) are major glycolipids present in the mycobacterial cell wall that are able to modulate the host immune response. In this study, we have undertaken the structural determination of these important modulins in Mycobacterium chelonae, a fast growing pathogenic mycobacterial species. One-dimensional and two-dimensional NMR spectra were used to demonstrate that LM and LAM from M. chelonae, designated CheLM and CheLAM, respectively, possess structures that differ from the ones reported earlier in other mycobacterial species. Analysis by gas chromatography/mass spectrometry of the phosphatidyl-myo-inositol anchor, which is thought to play a role in the biological functions of these lipoglycans, pointed to a high degree of heterogeneity based on numerous combinations of acyl groups on the C-1 and C-2 positions of the glycerol moiety. Characterization of the mannan core of CheLM and CheLAM revealed the presence of novel α1,3-mannopyranosyl side chains. This motif, which reacted specifically with the lectin from Galanthus nivalis, was found to be unique among a panel of nine mycobacterial species. Then, CheLM and CheLAM were found to be devoid of both the mannooligosaccharide cap present in Mycobacterium tuberculosis and the inositol phosphate cap present in Mycobacterium smegmatis and other fast growing species. Tumor necrosis factor-alpha and interleukin-8 production were assessed from human macrophages with LAM preparations from different species. Our results suggest that the inositol phosphate capping may represent the major cytokine-inducing component of LAMs. This work not only underlines the diversity of LAM structures among various mycobacterial species but also provides new structures that could be useful to dissect the structure-function relationships of these complex molecules.
lipopolysaccharides, antigens, cell wall, structural studies, Mycobacterium, glycolipid, immune response, lipoarabinomannan, tumor necrosis factor, CD1, interleukin-8, lectins, Mycobacterium chelonae
NCBI PubMed ID: 12063260Publication DOI: 10.1074/jbc.M204398200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: laurent.kremer@ibl.fr
Institutions: Laboratoire de Glycobiologie Structurale et Fonctionnelle, CNRS UMR8576, Universite des Sciences et Technologies de Lille, F-59655 Villeneuve Ascq Cedex, France, School of Biosciences, University of Birmingham, Edgbaston, Birmingham, B15 2TT United Kingdom, Laboratoire des Mecanismes Moleculaires de la Pathogenie
Methods: NMR-2D, NMR, MALDI-MS
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11. Compound ID: 3802
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a-D-Manp-(1-2)-a-D-Manp-(1-?)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-+
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a-D-Manp-(1-2)-a-D-Manp-(1-?)-b-D-Araf-(1-2)-a-D-Araf-(1-3)-a-D-Araf-(1-5)-a-D-Araf |
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Structure type: fragment of a bigger structure
Trivial name: arabinan in LAM
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_1309625,IEDB_134619,IEDB_136104,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_857717,IEDB_857718,IEDB_857722,IEDB_857723,IEDB_857726,IEDB_857727,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 1450
Chatterjee D, Khoo K "Mycobacterial lipoarabinomannan: an extraordinary lipoheteroglycan with profound physiological effects" -
Glycobiology 8(2) (1998) 113-120
Detailed structural and functional studies over the last decade have led to current recognition of the mycobacterial lipoarabinomannan (LAM) as a phosphatidylinositol anchored lipoglycan with diverse biological activities. Fatty acylation has been demonstrated to be essential for LAM to maintain its functional integrity although the focus has largely been on the arabinan motifs and the terminal capping function. It has recently been shown that the mannose caps may be involved not only in attenuating host immune response, but also in mediating the binding of mycobacteria to and subsequent entry into macrophages. This may further be linked to an intracellular trafficking pathway through which LAM is thought to be presented by CD1 to subsets of T-cells. The implication of LAM as major histocompatibility complex (MHC)-independent T-cell epitope and the ensuing immune response is an area of intensive studies. Another recent focus of research is the biosynthesis of arabinan which has been shown to be inhibitable by the anti-tuberculosis drug, ethambutol. The phenomenon of truncated LAM as synthesized by ethambutol resistant strains provides an invaluable handle for dissecting the array of arabinosyltransferases involved, as well as generating much needed structural variants for further structural and functional studies. It is hoped that with more systematic investigations based on clinical isolates and human cell lines, the true significance of LAM in the immunopathogenesis of tuberculosis and leprosy can eventually be explained.
structure, Mycobacteria, lipoarabinomannan, lipoglycan, tuberculosis, CD1, phosphatidylinositol, ethambutol, lipomannan, phosphatidylinositol mannosides
NCBI PubMed ID: 9451020Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO 80523, USA and Institute of Biological Chemistry, Academia Sinica, Taipei, Taiwan
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12. Compound ID: 3803
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a-D-Manp-(1-2)-a-D-Manp-(1-?)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-a-D-Araf |
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Structure type: structural motif or average structure
Trivial name: arabinan in LAM
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_1309625,IEDB_136104,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_857718,IEDB_857722,IEDB_857726,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 1450
Chatterjee D, Khoo K "Mycobacterial lipoarabinomannan: an extraordinary lipoheteroglycan with profound physiological effects" -
Glycobiology 8(2) (1998) 113-120
Detailed structural and functional studies over the last decade have led to current recognition of the mycobacterial lipoarabinomannan (LAM) as a phosphatidylinositol anchored lipoglycan with diverse biological activities. Fatty acylation has been demonstrated to be essential for LAM to maintain its functional integrity although the focus has largely been on the arabinan motifs and the terminal capping function. It has recently been shown that the mannose caps may be involved not only in attenuating host immune response, but also in mediating the binding of mycobacteria to and subsequent entry into macrophages. This may further be linked to an intracellular trafficking pathway through which LAM is thought to be presented by CD1 to subsets of T-cells. The implication of LAM as major histocompatibility complex (MHC)-independent T-cell epitope and the ensuing immune response is an area of intensive studies. Another recent focus of research is the biosynthesis of arabinan which has been shown to be inhibitable by the anti-tuberculosis drug, ethambutol. The phenomenon of truncated LAM as synthesized by ethambutol resistant strains provides an invaluable handle for dissecting the array of arabinosyltransferases involved, as well as generating much needed structural variants for further structural and functional studies. It is hoped that with more systematic investigations based on clinical isolates and human cell lines, the true significance of LAM in the immunopathogenesis of tuberculosis and leprosy can eventually be explained.
structure, Mycobacteria, lipoarabinomannan, lipoglycan, tuberculosis, CD1, phosphatidylinositol, ethambutol, lipomannan, phosphatidylinositol mannosides
NCBI PubMed ID: 9451020Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO 80523, USA and Institute of Biological Chemistry, Academia Sinica, Taipei, Taiwan
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13. Compound ID: 4342
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b-D-Galf-(1-6)-{{{-b-D-Galf-(1-5)-b-D-Galf-(1-6)-}}}+
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Mycolic-(1-5)-+ |
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Mycolic-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-+ |
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Mycolic-(1-5)-+ | {{{-a-D-Araf-(1-5)-}}}/n=7/-a-D-Araf-(1-3)-+ |
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Mycolic-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-3)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}a-D-Araf-(1-5)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}a-D-Araf-(1-5)-b-D-Galf-(1-5)-{{{-b-D-Galf-(1-6)-b-D-Galf-(1-5)-}}}/n=3/-a-D-Galf-(1-4)-b-L-Rhap-(1-4)-a-D-GlcpNAc-(1---P---/peptidoglycan/ |
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Structure type: oligomer
Aglycon: peptidoglycan
Trivial name: arabinogalactan
Contained glycoepitopes: IEDB_136095,IEDB_137340,IEDB_137472,IEDB_141807,IEDB_149176,IEDB_150077,IEDB_151531,IEDB_159255,IEDB_190606,IEDB_225177,IEDB_885812,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 1629
Li W, Chatterjee D, Lee RE "Rapid structural characterization of the arabinogalactan and lipoarabinomannan in live mycobacterial cells using 2D and 3D HR-MAS NMR: structural changes in the arabinan due to ethambutol treatment and gene mutation are observed" -
Glycobiology 15(2) (2005) 139-151
Mycobacteria possess a unique, highly evolved, carbohydrate- and lipid-rich cell wall that is believed to be important for their survival in hostile environments. Until now, our understanding of mycobacterial cell wall structure has been based upon destructive isolation and fragmentation of individual cell wall components. This study describes the observation of the major cell wall structures in live, intact mycobacteria using 2D and 3D high-resolution magic-angle spinning (HR-MAS) nuclear magnetic resonance (NMR). As little as 20 mg (wet weight) of [13C]-enriched cells were required to produce a whole-cell spectra in which discrete cross-peaks corresponding to specific cell wall components could be identified. The most abundant signals of the arabinogalactan (AG) and lipoarabinomannan (LAM) were assigned in the HR-MAS NMR spectra by comparing the 2D and 3D NMR whole-cell spectra with the spectra of purified cellular components. This study confirmed that the structures of the AG and LAM moieties in the cell wall of live mycobacteria are consistent with structural reports in the literature, which were obtained via degradative analysis. Most important, by using intact cells it was possible to directly demonstrate the effects of ethambutol on the mycobacterial cell wall polysaccharides, characterize the effects of embB gene knockout in the M. smegmatis ∆embB mutant, and observe differences in the cell wall structures of two mycobacterial species (M. bovis BCG and M. smegmatis.) Herein, we show that HR-MAS NMR is a powerful, rapid, nondestructive technique to monitor changes in the complex, carbohydrate-rich cell wall of live mycobacterial cells.
Mycobacteria, arabinogalactan, lipoarabinomannan, Mycobacterium smegmatis, HR-MAS NMR, HCCH-TOCSY, Mycobacterium bovis, mycolyl arabinogalactanstructure
NCBI PubMed ID: 15371346Publication DOI: 10.1093/glycob/cwh150Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: relee@utmem.edu
Institutions: Department of Pharmaceutical Sciences, University of Tennessee Health Science Center, 847 Monroe Ave. Rm. 327, Memphis, TN 38163, USA
Methods: NMR
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14. Compound ID: 4343
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{{{-a-D-Manp-(1-2)-}}}/n=0-2/-a-D-Manp-(1-5)-a-D-Araf-(1-2)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-+
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{{{-a-D-Manp-(1-2)-}}}/n=0-2/-a-D-Manp-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}a-D-Araf-(1-3)-{{{-a-D-Araf-(1-5)-}}}+
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{{{-a-D-Manp-(1-2)-}}}/n=0-2/-a-D-Manp-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-+ |
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{{{-a-D-Manp-(1-2)-}}}/n=0-2/-a-D-Manp-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-3)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}a-D-Araf-(1-3)-{{{-a-D-Araf-(1-5)-}}}{{{-a-D-Araf-(1-5)-}}}D-Araf-(1--/mannan core ID 10733/ |
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Structure type: oligomer
Aglycon: mannan core ID 10733
Trivial name: arabinan
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141795,IEDB_141830,IEDB_141834,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_164480,IEDB_1855257,IEDB_76933,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 1629
Li W, Chatterjee D, Lee RE "Rapid structural characterization of the arabinogalactan and lipoarabinomannan in live mycobacterial cells using 2D and 3D HR-MAS NMR: structural changes in the arabinan due to ethambutol treatment and gene mutation are observed" -
Glycobiology 15(2) (2005) 139-151
Mycobacteria possess a unique, highly evolved, carbohydrate- and lipid-rich cell wall that is believed to be important for their survival in hostile environments. Until now, our understanding of mycobacterial cell wall structure has been based upon destructive isolation and fragmentation of individual cell wall components. This study describes the observation of the major cell wall structures in live, intact mycobacteria using 2D and 3D high-resolution magic-angle spinning (HR-MAS) nuclear magnetic resonance (NMR). As little as 20 mg (wet weight) of [13C]-enriched cells were required to produce a whole-cell spectra in which discrete cross-peaks corresponding to specific cell wall components could be identified. The most abundant signals of the arabinogalactan (AG) and lipoarabinomannan (LAM) were assigned in the HR-MAS NMR spectra by comparing the 2D and 3D NMR whole-cell spectra with the spectra of purified cellular components. This study confirmed that the structures of the AG and LAM moieties in the cell wall of live mycobacteria are consistent with structural reports in the literature, which were obtained via degradative analysis. Most important, by using intact cells it was possible to directly demonstrate the effects of ethambutol on the mycobacterial cell wall polysaccharides, characterize the effects of embB gene knockout in the M. smegmatis ∆embB mutant, and observe differences in the cell wall structures of two mycobacterial species (M. bovis BCG and M. smegmatis.) Herein, we show that HR-MAS NMR is a powerful, rapid, nondestructive technique to monitor changes in the complex, carbohydrate-rich cell wall of live mycobacterial cells.
Mycobacteria, arabinogalactan, lipoarabinomannan, Mycobacterium smegmatis, HR-MAS NMR, HCCH-TOCSY, Mycobacterium bovis, mycolyl arabinogalactanstructure
NCBI PubMed ID: 15371346Publication DOI: 10.1093/glycob/cwh150Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: relee@utmem.edu
Institutions: Department of Pharmaceutical Sciences, University of Tennessee Health Science Center, 847 Monroe Ave. Rm. 327, Memphis, TN 38163, USA
Methods: NMR
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15. Compound ID: 4392
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b-D-Araf-(1-2)-a-D-Araf-(1-5)-+
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b-D-Araf-(1-2)-a-D-Araf-(1-3)-a-D-Araf-(1--/rest of arabinogalactan/ |
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Structure type: oligomer
Aglycon: rest of arabinogalactan
The structure is contained in the following publication(s):
- Article ID: 1657
Tropis M, Lemassu A, Vincent V, Daffé M "Structural elucidation of the predominant motifs of the major cell wall arabinogalactan antigens from the borderline species Tsukamurella paurometabolum and Mycobacterium fallax" -
Glycobiology 15(7) (2005) 677-686
Tsukamurella paurometabolum and Mycobacterium fallax are members of the suprageneric actinomycete group Corynebacterineae that possesses a cell wall skeleton composed of a peptidoglycan to which an arabinogalactan is covalently attached. This polysaccharide is further modified by esterification with C60-C80 mycolic acid residues in mycobacteria and T. paurometabolum. However, M. fallax and T. paurometabolum produce polyenoic (up to six double bonds) mycolic acids whereas the most common type of mycobacterial mycolates, called alpha-mycolates, are mono- and di-enoic or -cyclopropanated mycolic acids. To determine whether this difference also applied to the structures of cell wall arabinogalactans, competitive inhibition experiments using antibodies raised against the cell wall from Mycobacterium bovis and the arabinogalactans from T. paurometabolum and M. fallax were performed. They demonstrated the structural identity between the polysaccharide of M. fallax and those of mycobacteria and showed a strong similarity between the latter polysaccharides and that of T. paurometabolum. Structural analyses of the per-O-alkylated alditol fragments derived from the polysaccharides by gas chromatography-mass spectrometry (GC-MS) and 13C nuclear magnetic resonance (NMR) spectroscopy of the intact solubilized polysaccharides demonstrated that the polysaccharides from the two species analyzed contained all the major structural features previously characterized in mycobacterial arabinogalactans. These include (1) the homogalactan of alterning 5-linked galactofuranosyl (Galf) and 6-linked Galf residues, (2) a linear 5-linked arabino furanosyl (Araf), (3) a β-Araf-(1→2)-α-Araf disaccharide branched on both position 3 and position 5 of an α-Araf unit, and (4) a 5-linked-α-Araf unit branched on both position 3 and position 5 of an α-Araf residue. The polysaccharide from T. paurometabolum possesses additional structural domains composed of a terminal (t) Araf directly linked to either a 5-linked-α-Araf or to both position 3 and position 5 of a 3,5-linked α-Araf unit. Both the remarkable similarity of arabinogalactans from Corynebacterineae and their genus- and/or species-specificities are reflected in their 13C NMR spectra that may be used as a valuable help in the identification of members of the actinomycete group
cell wall, Mycobacterium, arabinogalactan, Tsukamurella
NCBI PubMed ID: 15761023Publication DOI: 10.1093/glycob/cwi052Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Institutions: Departement Mecanismes Moleculaires des Infections Mycobacteriennes, Institut de Pharmacologie et Biologie Structurale, UMR 5089 du Centre National de la Recherche Scientifique et de l'Universite Paul Sabatier, 31077 Toulouse cedex 04, France
Methods: NMR
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