Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_135394,IEDB_135515,IEDB_141181,IEDB_141807,IEDB_151531

• Article ID: 37
  Caroff M, Karibian D "Structure of bacterial lipopolysaccharides" - Carbohydrate Research 338(23) (2003) 2431-2447
  

  Bacterial lipopolysaccharides are the major components of the outer surface of Gram-negative bacteria They are often of interest in medicine for their immunomodulatory properties. In small amounts they can be beneficial, but in larger amounts they may cause endotoxic shock. Although they share a common architecture, their structural details exert a strong influence on their activity. These molecules comprise: a lipid moiety, called lipid A, which is considered to be the endotoxic component, a glycosidic part consisting of a core of approximately 10 monosaccharides and, in 'smooth-type' lipopolysaccharides, a third region, named O-chain, consisting of repetitive subunits of one to eight monosaccharides responsible for much of the immunospecificity of the bacterial cell.

  Lipopolysaccharide, structure, core, lipid A, endotoxin, O-chains

  NCBI PubMed ID: 14670707
  Publication DOI: 10.1016/j.carres.2003.07.010
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: martine.carloff@bbmpc.u-psud.fr
  Institutions: Equipe Endotoxines, UMR 8619 du Centre National de la Recherche Scientifique, IBBMC, Université de Paris-Sud, F-Orsay, France
  
   
  
  Yersinia pseudotuberculosis
  CSDB ID 31476 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_141584,IEDB_141807,IEDB_151531,IEDB_885822

• Article ID: 92
  Galbraith L, Wilkinson SG "Structures of the O21 and O25 antigens of Stenotrophomonas maltophilia" - Carbohydrate Research 323(1-4) (2000) 98-102
  

  The O-specific side-chain polymers from Stenotrophomonas maltophilia serogroups O21 and O25 were isolated from the lipopolysaccharides of the reference strains. The O21 polymer contained D-arabinose, 2-amino-2-deoxy-D-glucose and 2-amino-2-deoxy-D-galactose in equal proportions. Methylation analysis and NMR spectroscopy showed that the polysaccharide is based on a branched trisaccharide repeating unit of the structure shown below. The O25 polymer is linear with a disaccharide repeating unit identical to that forming the backbone of the O21 polymer

  Lipopolysaccharide, Stenotrophomonas maltophilia, O-specific polymer

  NCBI PubMed ID: 10782291
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: S.G.Wilkison@chem.hull.ac.uk
  Institutions: Faculty of Science and the Environment, Department of Chemistry, University of Hull, UK
  Methods: methylation, NMR-2D, NMR, sugar analysis
  
   
  
  Stenotrophomonas maltophilia O21
  CSDB ID 2092 (all data & tools)
• 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_3
  Publisher: Springer
  Correspondence: knirel@ioc.ac.ru
  Editors: Knirel YA, Valvano MA
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Stenotrophomonas maltophilia O21
  CSDB ID 27822 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_136907,IEDB_141181,IEDB_141807,IEDB_151531

• Article ID: 99
  Therisod H, Karibian D, Perry MB, Caroff M "Structural analysis of Yersinia pseudotuberculosis ATCC 29833 lipid A" - International Journal of Mass Spectrometry 219(3) (2002) 549-557
  

  The Yersinia genus includes human and animal pathogens (plague, enterocolitis) as well as non-pathogens. The lipopolysaccharide of the facultative pathogen Yersinia pseudotuberculosis has been implicated in the invasiveness of these bacteria. In this work, we have investigated the fine structure of the lipid A isolated from Y. pseudotuberculosis lipopolysaccharide using chemical analyses, gas chromatography/mass spectrometry, plasma desorption mass spectrometry, and matrix-assisted laser desorption mass spectrometry. Arabinose (Ara) and aminoarabinose (Ara-4N) esterified the phosphates as in Yersinia pestis lipid A. The acylation of Y. pseudotuberculosis lipid A differed from those found in Yersinia enterocolitica, Yersinia ruckeri, and Y. pestis lipopolysaccharides (LPSs): in the distribution of fatty acids between the two glucosamines in the fully acylated hexaacyl molecular species and by the acyloxyacyl substitution at position C-2′, where the Y. pseudotuberculosis lipid A has a C14OC16 making it closest to that of Y. pestis.

  lipid A, endotoxin, Yersinia pseudotuberculosis, Y. pseudotuberculosis, PDMS, MALDI

  Publication DOI: 10.1016/S1387-3806(02)00706-6
  Journal NLM ID: 101137096
  Publisher: Elsevier
  Correspondence: martine.caroff@bbmpc.u-psud.fr
  Institutions: Equipe “Endotoxines”, UMR 8619 du CNRS, I.B.B.M.C., Université de Paris-Sud, F-Orsay, France, Institute for Biological Sciences, NRC, Ottawa, Ont., Canada
  Methods: GC-MS, SDS-PAGE, TLC, ESI-MS, GC, MALDI-TOF MS, composition analysis, mild alkaline degradation, PD-MS
  
   
  
  Yersinia pseudotuberculosis ATCC 29833
  CSDB ID 5202 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipid A
Contained glycoepitopes: IEDB_136907,IEDB_141807,IEDB_151531,IEDB_534864,IEDB_581506

• Article ID: 99
  Therisod H, Karibian D, Perry MB, Caroff M "Structural analysis of Yersinia pseudotuberculosis ATCC 29833 lipid A" - International Journal of Mass Spectrometry 219(3) (2002) 549-557
  

  The Yersinia genus includes human and animal pathogens (plague, enterocolitis) as well as non-pathogens. The lipopolysaccharide of the facultative pathogen Yersinia pseudotuberculosis has been implicated in the invasiveness of these bacteria. In this work, we have investigated the fine structure of the lipid A isolated from Y. pseudotuberculosis lipopolysaccharide using chemical analyses, gas chromatography/mass spectrometry, plasma desorption mass spectrometry, and matrix-assisted laser desorption mass spectrometry. Arabinose (Ara) and aminoarabinose (Ara-4N) esterified the phosphates as in Yersinia pestis lipid A. The acylation of Y. pseudotuberculosis lipid A differed from those found in Yersinia enterocolitica, Yersinia ruckeri, and Y. pestis lipopolysaccharides (LPSs): in the distribution of fatty acids between the two glucosamines in the fully acylated hexaacyl molecular species and by the acyloxyacyl substitution at position C-2′, where the Y. pseudotuberculosis lipid A has a C14OC16 making it closest to that of Y. pestis.

  lipid A, endotoxin, Yersinia pseudotuberculosis, Y. pseudotuberculosis, PDMS, MALDI

  Publication DOI: 10.1016/S1387-3806(02)00706-6
  Journal NLM ID: 101137096
  Publisher: Elsevier
  Correspondence: martine.caroff@bbmpc.u-psud.fr
  Institutions: Equipe “Endotoxines”, UMR 8619 du CNRS, I.B.B.M.C., Université de Paris-Sud, F-Orsay, France, Institute for Biological Sciences, NRC, Ottawa, Ont., Canada
  Methods: GC-MS, SDS-PAGE, TLC, ESI-MS, GC, MALDI-TOF MS, composition analysis, mild alkaline degradation, PD-MS
  
   
  
  Yersinia pestis, Yersinia ruckeri
  CSDB ID 31386 (all data & tools)

Show legend Show as text

Structure type: fragment of a bigger structure
Trivial name: nonreducing terminal epitope of lipoarabinomannan
Contained glycoepitopes: IEDB_1309625,IEDB_134619,IEDB_857717,IEDB_857718

• 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_1
  Publisher: Berlin, Heidelberg: Springer.
  Editors: Shinnick TM
  Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO, 80523, USA
  
   
  
  Mycobacterium tuberculosis
  CSDB ID 31420 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: core of lipoarabinomannan
Compound class: LPS
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141793,IEDB_141828,IEDB_141829,IEDB_141831,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_76933,IEDB_857732,IEDB_857735,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

• 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_1
  Publisher: Berlin, Heidelberg: Springer.
  Editors: Shinnick TM
  Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO, 80523, USA
  
   
  
  Mycobacterium tuberculosis
  CSDB ID 31421 (all data & tools)

Show legend Show as text

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

• 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_1
  Publisher: Berlin, Heidelberg: Springer.
  Editors: Shinnick TM
  Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO, 80523, USA
  
   
  
  Mycobacterium tuberculosis
  CSDB ID 31422 (all data & tools)

Show legend Show as text

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

• 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_1
  Publisher: Berlin, Heidelberg: Springer.
  Editors: Shinnick TM
  Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO, 80523, USA
  
   
  
  Mycobacterium tuberculosis
  CSDB ID 31423 (all data & tools)

Show legend Show as text

Structure type: homopolymer
Trivial name: arabinan, arabinan fragmemnt of the lipoarabinomannan
Compound class: arabinogalactan, arabinan part of arabinogalactan

• 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_1
  Publisher: Berlin, Heidelberg: Springer.
  Editors: Shinnick TM
  Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO, 80523, USA
  
   
  
  Mycobacterium tuberculosis
  CSDB ID 31426 (all data & tools)
• Article ID: 2645
  Daffé M, Brennan PJ, McNeil M "Predominant structural features of the cell wall arabinogalactan of Mycobacterium tuberculosis as revealed through characterization of oligoglycosyl alditol fragments by gas chromatography/mass spectrometry and by proton and carbon-13 NMR analyses" - Journal of Biological Chemistry 265 (1990) 6734-6743
  

  The peptidoglycan-bound arabinogalactan of a virulent strain of Mycobacterium tuberculosis was per-O-methylated, partially hydrolyzed with acid, and the resulting oligosaccharides reduced and O-pentadeute-rioethylated. The per-O-alkylated oligoglycosyl alditol fragments were separated by high pressure liquid chromatography and the structures of 43 of these constituents determined by 1H NMR and gas chromatography/mass spectrometry. The arabinogalactan was shown to consist of a galactan containing alternating 5-linked β-D-galactofuranosyl (Galf) and 6-linked β-D-Galf residues. The arabinan chains are attached to C-5 of some of the 6-linked Galf residues. The arabinan is comprised of at least three major structural domains. One is composed of linear 5-linked α-D-arabinofuranosyl (Araf) residues; a second consists of branched 3,5-linked α-D-Araf units substituted with 5-linked α-D-Araf residues at both branched positions. The non-reducing terminal region of the arabinan was characterized by a 3,5-linked α-D-Araf residue substituted at both branched positions with the disaccharide β-D-Araf-(1→2)-α-D-Araf. 13C NMR of intact soluble arabinogalactan established the presence of both α- and β-Araf residues in this domain. This non-reducing terminal motif apparently provides the structural basis of the dominant immunogenicity of arabinogalactan within mycobacteria. A rhamnosyl residue occupies the reducing terminus of the galactan core and may link the arabinogalactan to the peptidoglycan. Evidence is also presented for the presence of minor structural features involving terminal mannopyranosyl units. Models for most of the heteropolysaccharide are proposed which should increase our understanding of a molecule responsible for much of the immunogenicity, pathogenicity, and peculiar physical properties of the mycobacterial cell.

  NCBI PubMed ID: 2108960
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
  
   
  
  Mycobacterium tuberculosis
  CSDB ID 135836 (all data & tools)
• Article ID: 4525
  Grzegorzewicz AE, Jackson M "Subfractionation and analysis of the cell envelope (lipo)polysaccharides of Mycobacterium tuberculosis" - Book: Methods in Molecular Biology (2013) Vol. 966, 309-324
  

  The cell envelope of Mycobacterium tuberculosis, the causative agent of tuberculosis in humans, is the source of carbohydrates of exceptional structure which play essential roles in the physiology of the bacterium and in its interactions with the host during infection. Much of what is known about their biosynthesis was derived from the phenotypic analysis of knockout or conditional knockout mutants of mycobacteria generated by random or specific insertional mutagenesis. Here, we describe the current techniques used to subfractionate M. tuberculosis cells and investigate major quantitative and qualitative changes in their cell envelope (lipo)polysaccharides.

  capsule, arabinogalactan, lipoarabinomannan, Mycobacterium tuberculosis, glucan, lipomannan

  NCBI PubMed ID: 23299743
  Publication DOI: 10.1007/978-1-62703-245-2_19
  Publisher: Totowa, NJ: Humana Press
  Correspondence: Mary.Jackson@colostate.edu
  Editors: Holst O, Walker JM, Beck A
  Institutions: Mycobacteria Research Laboratories, Department of Microbiology, Immunology, and Pathology, Colorado State University, Fort Collins, CO, USA
  Methods: mild acid hydrolysis, alkaline degradation, biochemical methods, HPLC, SDS-Tricine-PAGE
  
   
  
  Mycobacterium tuberculosis
  CSDB ID 29528 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: galactan
Compound class: arabinogalactan
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_149137,IEDB_149176,IEDB_190606,IEDB_885812

• 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_1
  Publisher: Berlin, Heidelberg: Springer.
  Editors: Shinnick TM
  Institutions: Department of Microbiology, Colorado State University, Fort Collins, CO, 80523, USA
  
   
  
  Mycobacterium tuberculosis
  CSDB ID 31428 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: lipoarabinomannan
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_136907,IEDB_140116,IEDB_141793,IEDB_141828,IEDB_141829,IEDB_141831,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_857732,IEDB_857735,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

• Article ID: 637
  Garton NJ, Gilleron M, Brando T, Dan HH, Giguere S, Puzo G, Prescott JF, Sutcliffe IC "A novel lipoarabinomannan from the equine pathogen Rhodococcus equi. Structure and effect on macrophage cytokine production" - Journal of Biological Chemistry 277(35) (2002) 31722-31733
  

  Rhodococcus equi is a major cause of foal morbidity and mortality. We have investigated the presence of lipoglycan in this organism as closely related bacteria, notably Mycobacterium tuberculosis, produce lipoarabinomannans (LAM) that may play multiple roles as virulence determinants. The lipoglycan was structurally characterized by gas chromatography-mass spectrometry following permethylation, capillary electrophoresis after chemical degradation, and (1)H and (31)P and two-dimensional heteronuclear nuclear magnetic resonance studies. Key structural features of the lipoglycan are a linear α-1,6-mannan with side chains containing one 2-linked α-D-Manp residue. This polysaccharidic backbone is linked to a phosphatidylinositol mannosyl anchor. In contrast to mycobacterial LAM, there are no extensive arabinan domains but single terminal α-D-Araf residue capping the 2-linked α-D-Manp. The lipoglycan binds concanavalin A and mannose-binding protein consistent with the presence of t-α-D-Manp residues. We studied the ability of the lipoglycans to induce cytokines from equine macrophages, in comparison to whole cells of R. equi. These data revealed patterns of cytokine mRNA induction that suggest that the lipoglycan is involved in much of the early macrophage cytokine response to R. equi infection. These studies identify a novel LAM variant that may contribute to the pathogenesis of disease caused by R. equi.

  lipoarabinomannan, cytokines, macrophages, Rhodococcus equi

  NCBI PubMed ID: 12072437
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: iain.sutcliffe@sunderland.ac.uk
  Institutions: Institute of Pharmacy, Chemistry and Biomedical Sciences, the University of Sunderland, Sunderland SR2 3SD, United Kingdom, Institut de Pharmacologie et de Biologie Structurale du CNRS, 205 Route de Narbonne, 31077 Toulouse Cedex 4, France, the Department of Pathobiology, University of Guelph, Guelph, Ontario N1G 2W1, Canada, College of Veterinary Medicine, University of Florida, Gainesville, Florida 32610-0136
  Methods: NMR-2D, NMR, Western blotting, MALDI-TOF MS, electrophoresis, permethylation, capillary electrophoresis (CE), acetolysis
  
   
  
  Rhodococcus equi
  CSDB ID 407 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_149176,IEDB_190606

• Article ID: 673
  Gurjar MK, Reddy LK, Hotha S "Synthesis of oligosaccharides of motifs D and E of arabinogalactan present in Mycobacterium tuberculosis" - Journal of Organic Chemistry 66(13) (2001) 4657-4660
  

  Syntheses of the ethyl glycosides of 5-O-(β-D-galactofuranosyl)-β-D-galactofuranose and 5-O-(α-D-arabinofuranosyl)-6-O-(β-D-galactofuranosyl)-β-D-galactofuranose present in motifs D and E of Mycobacterium tuberculosis arabinogalactan, respectively, have been presented. The pentenyl-mediated O-glycosylation reaction was utilized to obtain the disaccharide of motif D. The first coupling reaction to prepare the inner disaccharide portion of motif E was accomplished by trichloroacetamidate method while the installation of the terminal sugar by pentenyl glycosylation approach was successful.

  synthesis, oligosaccharide, Oligosaccharides, motif, Mycobacterium, Mycobacteria, arabinogalactan, Mycobacterium tuberculosis, tuberculosis

  NCBI PubMed ID: 11421788
  Journal NLM ID: 2985193R
  Publisher: Columbus, OH: American Chemical Society
  Correspondence: gurjar@dalton.ncl.res.in
  
   
  
  Mycobacterium tuberculosis
  CSDB ID 469 (all data & tools)

Show legend Show as text

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

• 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: 11073941
  Journal NLM ID: 2985121R
  Publisher: 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
  
   
  
  Mycobacterium tuberculosis CSU19, Mycobacterium avium 2151
  CSDB ID 880 (all data & tools)

Show legend Show as text

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

• 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: 11073941
  Journal NLM ID: 2985121R
  Publisher: 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
  
   
  
  Mycobacterium tuberculosis CSU19, Mycobacterium avium 2151
  CSDB ID 916 (all data & tools)

Show legend Show as text

Structure type: oligomer

• Article ID: 796
  D'Souza FW, Ayers JD, McCarren PR, Lowary TL "Arabinofuranosyl oligosaccharides from mycobacteria: Synthesis and effect of glycosylation on ring conformation and hydroxymethyl group rotamer populations" - Journal of the American Chemical Society 122(7) (2000) 1251-1260
  

  A series of a-D-arabinofuranosyl oligosaccharides (2-8) that are fragments of the arabinan portions of two polysaccharides present in the cell wall of Mycobacterium tuberculosis have been synthesized. Preparation of the oligosaccharides involved the sequential addition of arabinofuranosyl residues from thioglycoside donors to methyl glycoside acceptors. High-resolution NMR studies on the final products provided all 3JH,H values, which were in turn used in PSEUROT 6.2 calculations to determine both the identity and equilibrium populations of preferred conformers for each furanose ring in these glycans. Comparison of the ring conformers present in 2-8 with those available in the parent monosaccharide, methyl a-D-arabinofuranose (16), allowed the determination of the effect of glycosylation upon ring conformation. At equilibrium, 16 exists as an approximately equimolar mixture of OT4 (North, N) and 2T3 (South, S) conformers. These studies showed that glycosylation of 16 at OH5 resulted in no significant change in conformer identity or population relative to 16. However, glycosylation of OH3 resulted in a change in the identity of the N species (to OE) and a significant favoring of this conformer at equilibrium. These trends were seen in all of the oligosaccharides. The populations of the three possible staggered rotamers (gg, gt, tg) about the C4-C5 bond were essentially the same for all residues in 2-8, and thus this equilibrium does not appear to be sensitive to glycosylation.

  conformation, synthesis, oligosaccharide, group, Oligosaccharides, Mycobacterium, Mycobacteria, population, glycosylation, effect, ring, hydroxymethyl, rotamer

  Journal NLM ID: 7503056
  Publisher: American Chemical Society
  Institutions: Contribution from the Department of Chemistry, The Ohio State University, 100 West 18th AVenue, Columbus, Ohio 43210
  Methods: NMR
  
   
  
  Mycobacterium tuberculosis
  CSDB ID 1279 (all data & tools)