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_144993,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: 302
  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: polymer chemical repeating unit
Trivial name: lipoarabiomannan
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: 537
  Ma Z, Zhang J, Kong F "Facile synthesis of arabinomannose penta- and decasaccharide fragments of the lipoarabinomannan of the equine pathogen, Rhodococcus equi" - Carbohydrate Research 339(10) (2004) 1761-1771
  

  Pentasaccharide repeating unit 20 of the lipoarabinomannan from the equine pathogen, Rhodococcus equi, and its dimer 31, were synthesized. The pentasaccharide was obtained by assembling a benzoylated 2,6-branched mannosyl trisaccharide acceptor 13 with a free hydroxyl group at C-2(') of the mannose residue attached to the core mannose residue by (1 [Formula: see text] 6)-linkage, followed by coupling with 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1 [Formula: see text] 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (18), and by deacylation. Meanwhile, the decamer 31 was obtained by firstly preparing a benzoylated mannose (1 [Formula: see text] 6)-linked tetrasaccharide backbone 26 with 2-, 2'-O-ClAc, and 2(')-, 2?-O-Ac groups, respectively, then by dechloroacetylation and subsequent condensation with perbenzoylated trichloroacetimidate, and then by deacetylation and subsequent coupling with 18, and finally, by deacylation

  arabinose, Mannose, Regio- and stereoselective synthesis

  NCBI PubMed ID: 15220086
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: fzkong@mail.rcees.ac.cn
  Institutions: Research Center for Eco-Environmental Sciences, Academia Sinica, PO Box 2871, Beijing 100085, PR China
  
   
  
  Rhodococcus equi
  CSDB ID 9270 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: repeating unit of lipoarabiomannan
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_76933,IEDB_857732,IEDB_857735,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

• Article ID: 537
  Ma Z, Zhang J, Kong F "Facile synthesis of arabinomannose penta- and decasaccharide fragments of the lipoarabinomannan of the equine pathogen, Rhodococcus equi" - Carbohydrate Research 339(10) (2004) 1761-1771
  

  Pentasaccharide repeating unit 20 of the lipoarabinomannan from the equine pathogen, Rhodococcus equi, and its dimer 31, were synthesized. The pentasaccharide was obtained by assembling a benzoylated 2,6-branched mannosyl trisaccharide acceptor 13 with a free hydroxyl group at C-2(') of the mannose residue attached to the core mannose residue by (1 [Formula: see text] 6)-linkage, followed by coupling with 2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl-(1 [Formula: see text] 2)-3,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (18), and by deacylation. Meanwhile, the decamer 31 was obtained by firstly preparing a benzoylated mannose (1 [Formula: see text] 6)-linked tetrasaccharide backbone 26 with 2-, 2'-O-ClAc, and 2(')-, 2?-O-Ac groups, respectively, then by dechloroacetylation and subsequent condensation with perbenzoylated trichloroacetimidate, and then by deacetylation and subsequent coupling with 18, and finally, by deacylation

  arabinose, Mannose, Regio- and stereoselective synthesis

  NCBI PubMed ID: 15220086
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: fzkong@mail.rcees.ac.cn
  Institutions: Research Center for Eco-Environmental Sciences, Academia Sinica, PO Box 2871, Beijing 100085, PR China
  
   
  
  Rhodococcus equi
  CSDB ID 9453 (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: 636
  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, CE, acetolysis
  
   
  
  Rhodococcus equi
  CSDB ID 407 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: EPS
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141111,IEDB_141793,IEDB_141828,IEDB_141829,IEDB_141830,IEDB_141831,IEDB_141832,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_164174,IEDB_164175,IEDB_164176,IEDB_174840,IEDB_76933,IEDB_857732,IEDB_857735,IEDB_983930,SB_136,SB_191,SB_196,SB_197,SB_198,SB_44,SB_67,SB_72

• Article ID: 779
  Corsaro MM, Evidente A, Lanzetta R, Lavermicocca P, Molinaro A "Structural determination of the phytotoxic mannan exopolysaccharide from Pseudomonas syringae pv. ciccaronei" - Carbohydrate Research 330(2) (2001) 271-277
  

  The structural determination was performed of a mannan exopolysaccharide from the gram negative bacterium Pseudomonas syringae pv. ciccaronei, which is the pathogenic agent responsible for the leaf spots of carob plants. The structure, obtained by chemical, enzymatic and spectroscopic methods, consisted of a backbone of α-(1→6)-linked mannopyranose units with 80% substituted at C-2 by mono-, di- and trisaccharide side chains. In addition, terminal glucose units and phosphate groups were found to be present. This is, to the best of our knowledge, the first report of a mannan exopolysaccharide structure from a phytopathogenic bacterium. The pure polysaccharide showed phytotoxic effects, i.e., chlorosis and necrosis on tobacco leaves.

  structural, Pseudomonas, determination, structural determination, exopolysaccharide, Pseudomonas syringae, mannan, Carob, phytotoxicity

  NCBI PubMed ID: 11217981
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: lanzetta@unina.it
  Institutions: Dipartimento di Chimica Organica e Biologica, Universita di Napoli Federico II, 6ia Mezzocannone 16, I- 80134 Napoli, Italy, Dipartimento di Science Chimico-Agrarie, Universita di Napoli Federico II, via Universita 100, I- 80055 Portici, Italy, Istituto Tossine e Micotossine da Parassiti Vegetali, CNR, viale Einaudi 51, I- 70125 Bari, Italy
  Methods: methylation, enzymatic hydrolysis, acid hydrolysis, acetolysis, determination of absolute configuration
  
   
  
  Pseudomonas syringae pv. ciccaronei NCPPB2355
  CSDB ID 1248 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: LAM
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: 697
  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: 12063260
  Publication DOI: 10.1074/jbc.M204398200
  Journal NLM ID: 2985121R
  Publisher: 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
  
   
  
  Mycobacterium tuberculosis BCG, Mycobacterium bovis BCG, Mycobacterium smegmatis
  CSDB ID 611 (all data & tools)

Show legend Show as text

Structure type: oligomer
Aglycon: MPI anchor
Trivial name: mannan
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: 1628
  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: 15371346
  Publication DOI: 10.1093/glycob/cwh150
  Journal NLM ID: 9104124
  Publisher: 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
  
   
  
  Mycobacterium tuberculosis, Mycobacterium bovis
  CSDB ID 10733 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: phosphomannan
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141793,IEDB_141828,IEDB_141829,IEDB_141830,IEDB_141831,IEDB_141832,IEDB_143632,IEDB_144983,IEDB_144996,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: 1637
  Paramonov N, Rangarajan M, Hashim A, Gallagher A, duse-Opoku J, Slaney JM, Hounsell E, Curtis MA "Structural analysis of a novel anionic polysaccharide from Porphyromonas gingivalis strain W50 related to Arg-gingipain glycans" - Molecular Microbiology 58(3) (2005) 847-863
  

  The Arg-gingipains (RgpsA and B) of Porphyromonas gingivalis are a family of extracellular cysteine proteases and are important virulence determinants of this periodontal bacterium. A monoclonal antibody, MAb1B5, which recognizes an epitope on glycosylated monomeric RgpAs also cross-reacts with a cell-surface polysaccharide of P. gingivalis W50 suggesting that the maturation pathway of the Arg-gingipains may be linked to the biosynthesis of a surface carbohydrate. We report the purification and structural characterization of the cross-reacting anionic polysaccharide (APS), which is distinct from both the lipopolysaccharide and serotype capsule polysaccharide of P. gingivalis W50. The structure of APS was determined by 1D and 2D NMR spectroscopy and methylation analysis, which showed it to be a phosphorylated branched mannan. The backbone is built up of α-1,6-linked mannose residues and the side-chains contain α-1,2-linked mannose oligosaccharides of different lengths (one to two sugar residues) attached to the backbone via 1,2-linkage. One of the side-chains in the repeating unit contains Manα1-2Manα1-phosphate linked via phosphorus to a backbone mannose at position 2. De-O-phosphorylation of APS abolished cross-reactivity suggesting that Manα1-2Manα1-phosphate fragment forms part of the epitope recognized by MAb1B5. This phosphorylated branched mannan represents a novel polysaccharide that is immunologically related to the post-translational additions of Arg-gingipains.

  Lipopolysaccharide, NMR, biosynthesis, oligosaccharide, structure, branched, Pathogenesis, disease, strain, structural, virulence, characterization, polysaccharide, serotype, methylation analysis, repeating unit, analysis, determinant, structural analysis, carbohydrate, cell, group, linked, molecular, side chain, form, antibodies, antibody, epitope, monoclonal, monoclonal antibodies, monoclonal antibody, Oligosaccharides, NMR spectroscopy, infectious disease, bacteria, glycan, sugar, families, methylation, position, medicine, spectroscopy, surface, backbone, phosphorylated, capsule, Infectious, fragment, extracellular, pathway, 2D NMR spectroscopy, capsule polysaccharide, cross-reactivity, crossreactivity, 2D NMR, Mannose, purification, mannan, phosphorus, glycosylated, Arg-gingipain, Porphyromonas, Porphyromonas gingivalis, anionic, P, protease, Cysteine

  NCBI PubMed ID: 16238632
  Journal NLM ID: 8712028
  Publisher: Blackwell Publishing
  Institutions: MRC Molecular Pathogenesis Group, Centre for Infectious Disease, Institute of Cell and Molecular Science, Barts and The London, Queen Mary's School of Medicine and Dentistry, 4 Newark Street, London E1 2AT, UK
  Methods: methylation, NMR
  
   
  
  Porphyromonas gingivalis W50
  CSDB ID 10595 (all data & tools)
• Article ID: 3364
  Nikolaev AV, Botvinko IV, Ross AJ "Natural phosphoglycans containing glycosyl phosphate units: structural diversity and chemical synthesis" - Carbohydrate Research 342(3-4) (2007) 297-344
  

  An anomeric phosphodiester linkage formed by a glycosyl phosphate unit and a hydroxyl group of another monosaccharide is found in many glycopolymers of the outer membrane in bacteria (e.g., capsular polysaccharides and lipopolysaccharides), yeasts and protozoa. The polymers (phosphoglycans) composed of glycosyl phosphate (or oligoglycosyl phosphate) repeating units could be chemically classified as poly(glycosyl phosphates). Their importance as immunologically active components of the cell wall and/or capsule of numerous microorganisms upholds the need to develop routes for the chemical preparation of these biopolymers. In this paper, we (1) present a review of the primary structures (known to date) of natural phosphoglycans from various sources, which contain glycosyl phosphate units, and (2) discuss different approaches and recent achievements in the synthesis of glycosyl phosphosaccharides and poly(glycosyl phosphates).

  synthesis, structure, polysaccharides, Phosphoglycans, Anomeric phosphodiesters

  NCBI PubMed ID: 17092493
  Publication DOI: 10.1016/j.carres.2006.10.006
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: a.v.nikolaev@dundee.ac.uk
  Institutions: College of Life Sciences, Division of Biological Chemistry and Molecular Microbiology, University of Dundee, Dundee DD1 5EH, UK.
  
   
  
  Porphyromonas gingivalis W50
  CSDB ID 21789 (all data & tools)

Show legend Show as text

Structure type: oligomer
Aglycon: Glycerol
Trivial name: ManLAM, mannan-Ins core
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_76933,IEDB_857732,IEDB_857735,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

• Article ID: 2496
  Chatterjee D, Khoo KH, McNeil MR, Dell A, Morris HR, Brennan PJ "Structural definition of the non-reducing termini of mannose-capped LAM from Mycobacterium tuberculosis through selective enzymatic degradation and fast atom bombardment-mass spectrometry" - Glycobiology 3 (1993) 497-506
  
  Journal NLM ID: 9104124
  Publisher: IRL Press at Oxford University Press
  
   
  
  Mycobacterium tuberculosis
  CSDB ID 126818 (all data & tools)

Show legend Show as text

Structure type: oligomer
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_76933,IEDB_857732,IEDB_857735,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

• Article ID: 2890
  Venisse A, Rivière M, Vercauteren J, Puzo G "Structural analysis of the mannan region of lipoarabinomannan from Mycobacterium bovis BCG - Heterogeneity in phosphorylation state" - Journal of Biological Chemistry 270 (1995) 15012-15021
  

  Lipoarabinomannan (LAM) is a major antigen of mycobacterial cell walls, involved in host-Mycobacterium interactions. In a previous work, LAM from the vaccine strain, Mycobacterium bovis BCG, was found to exhibit mannooligosaccharides at its arabinan nonreducing ends (ManLAM). The present report concerns the mannan core structure of this ManLAM. After partial hydrolysis of ManLAM, two populations of mannans (Ma1 and Ma2) were obtained by gel filtration chromatography. Their structural features were defined by means of two-dimensional homo- and heteronuclear (1H-13C) NMR sequences and methylation analysis. They were both found to be composed of an α-(1→6)-linked mannan backbone with α-(1→2)-Manp-linked side chains. They are highly branched, and Ma2 presents a higher frequency of branching than Ma1. Moreover, chemical analysis indicates that only Ma1 is phosphorylated. By a two-dimensional heteronuclear 1H-31P total correlation experiment, the phosphate was found to be involved in a phosphodiester bond between inositol C-1 and glycerol C-3. Then, the molecular mass of mannan was established by mass spectrometry, which revealed a molecular mass of 3517 Da for the major molecular species of Ma1. Likewise, analysis of unfractionated mannans showed the occurrence of other, quantitatively minor molecular species, endowed with two phosphates. This study clearly indicates that the mannan region of M. bovis BCG ManLAM exists as a heterogeneous population of molecules whose structures differ in their degree of glycosylation, level of branching, and phosphorylation state. The hypothesis that the relative abundance of these different molecules modulates the biological functions of LAM is discussed.

  NCBI PubMed ID: 7797482
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Institutions: Laboratoire de Pharmacologie et de Toxicologie Fondamentales du CNRS, Département III, Toulouse, France
  
   
  
  Mycobacterium bovis BCG
  CSDB ID 137537 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_136907,IEDB_137485,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: 2890
  Venisse A, Rivière M, Vercauteren J, Puzo G "Structural analysis of the mannan region of lipoarabinomannan from Mycobacterium bovis BCG - Heterogeneity in phosphorylation state" - Journal of Biological Chemistry 270 (1995) 15012-15021
  

  Lipoarabinomannan (LAM) is a major antigen of mycobacterial cell walls, involved in host-Mycobacterium interactions. In a previous work, LAM from the vaccine strain, Mycobacterium bovis BCG, was found to exhibit mannooligosaccharides at its arabinan nonreducing ends (ManLAM). The present report concerns the mannan core structure of this ManLAM. After partial hydrolysis of ManLAM, two populations of mannans (Ma1 and Ma2) were obtained by gel filtration chromatography. Their structural features were defined by means of two-dimensional homo- and heteronuclear (1H-13C) NMR sequences and methylation analysis. They were both found to be composed of an α-(1→6)-linked mannan backbone with α-(1→2)-Manp-linked side chains. They are highly branched, and Ma2 presents a higher frequency of branching than Ma1. Moreover, chemical analysis indicates that only Ma1 is phosphorylated. By a two-dimensional heteronuclear 1H-31P total correlation experiment, the phosphate was found to be involved in a phosphodiester bond between inositol C-1 and glycerol C-3. Then, the molecular mass of mannan was established by mass spectrometry, which revealed a molecular mass of 3517 Da for the major molecular species of Ma1. Likewise, analysis of unfractionated mannans showed the occurrence of other, quantitatively minor molecular species, endowed with two phosphates. This study clearly indicates that the mannan region of M. bovis BCG ManLAM exists as a heterogeneous population of molecules whose structures differ in their degree of glycosylation, level of branching, and phosphorylation state. The hypothesis that the relative abundance of these different molecules modulates the biological functions of LAM is discussed.

  NCBI PubMed ID: 7797482
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Institutions: Laboratoire de Pharmacologie et de Toxicologie Fondamentales du CNRS, Département III, Toulouse, France
  
   
  
  Mycobacterium bovis BCG
  CSDB ID 137538 (all data & tools)

Show legend Show as text

Structure type: structural motif or average structure
Trivial name: arabinomannan
Contained glycoepitopes: IEDB_130701,IEDB_1309625,IEDB_136104,IEDB_140116,IEDB_141793,IEDB_141828,IEDB_141829,IEDB_141830,IEDB_141831,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_1855257,IEDB_76933,IEDB_857718,IEDB_857732,IEDB_857735,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

• Article ID: 2663
  Venisse A, Berjeaud JM, Chaurand P, Gilleron M, Puzo G "Structural features of lipoarabinomannan from Mycobacterium bovis BCG. Determination of molecular mass by laser desorption mass spectrometry" - Journal of Biological Chemistry 268 (1993) 12401-12411
  

  It was recently shown that mycobacterial lipoarabinomannan (LAM) can be classified into two types (Chatterjee, D., Lowell, K., Rivoire B., McNeil M. R., and Brennan, P. J. (1992) J. Biol. Chem. 267, 6234-6239) according to the presence or absence of mannosyl residues (Manp) located at the nonreducing end of the oligoarabinosyl side chains. These two types of LAM were found in a pathogenic Mycobacterium tuberculosis strain and in an avirulent M. tuberculosis strain, respectively, suggesting that LAM with Manp characterizes virulent and "disease-inducing strains." We now report the structure of the LAM from Mycobacterium bovis Bacille Calmette-Guérin (BCG) strain Pasteur, largely used throughout the world as vaccine against tuberculosis. Using an up-to-date analytical approach, we found that the LAM of M. bovis BCG belongs to the class of LAMs capped with Manp. By means of two-dimensional homonuclear and heteronuclear scalar coupling NMR analysis and methylation data, the sugar spin system assignments were partially established, revealing that the LAM contained two types of terminal Manp and 2-O-linked Manp. From the following four-step process: (i) partial hydrolysis of deacylated LAM (dLAM), (ii) oligosaccharide derivatization with aminobenzoic ethyl ester, (iii) HPLC purification, (iv) FAB/MS-MS analysis; it was shown that the dimannosyl unit α-D-Manp-(1→2)-α-D-Manp is the major residue capping the termini of the arabinan of the LAM. In this report, LAM molecular mass determination was established using matrix-assisted UV-laser desorption/ionization mass spectrometry which reveals that the LAM molecular mass is around 17.4 kDa. The similarity of the LAM structures between M. bovis BCG and M. tuberculosis H37Rv is discussed in regard to their function in the immunopathology of mycobacterial infection.

  NCBI PubMed ID: 8509380
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Institutions: Centre National de la Recherche Scientifique, Département Glycoconjugués et Biomembranes, Toulouse, France
  Methods: 1H NMR, FAB-MS/MS, LD-MS
  
   
  
  Mycobacterium bovis BCG
  CSDB ID 186631 (all data & tools)
• Article ID: 3114
  Venisse A, Fournié JJ, Puzo G "Mannosylated lipoarabinomannan interacts with phagocytes" - European Journal of Biochemistry 231 (1995) 440-447
  

  Infection by Mycobacterium tuberculosis first involves its adhesion to mononuclear host phagocytes. Various macrophage opsonic and non-opsonic receptors are known to mediate this adhesion, with some specificity of mannosyl receptors for the more virulent strains. Mannosylated lipoarabinomannan, a major component of cell walls from M. tuberculosis and Mycobacterium bovis BCG, is endowed with mannooligosaccharide units that could mediate its binding to these latter receptors. To explore its interaction with murine immune cells by flow cytometry, we report a new procedure to fluorescently tag the polysaccharide molecules. We covalently labeled mannosylated lipoarabinomannan from M. bovis BCG with biotin, allowing formation of stable complexes with streptavidin coupled to a fluorochrome. In this work, we demonstrated that this major carbohydrate antigen interacts selectively with murine phagocytes, i.e. granulocytes and macrophages. This binding was affected by temperature and was serum- and divalent-cation-dependent. It also appears to involve a metabolically recycling protein receptor on the phagocyte surface and mannosyl aggretopes on the mannosylated lipoarabinomannan molecule. Thus, the latter may provide a means for mycobacteria to bind to and invade their host phagocytes. This molecule could constitute one of the early factors of mycobacterial virulence.

  NCBI PubMed ID: 7635156
  Publication DOI: 10.1111/j.1432-1033.1995.tb20717.x
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Institutions: Departement des Glycoconjugues et Biomembranes, Laboratoire de Pharmacologie et Toxicologie Fondamentales du CNRS, Toulouse, France
  
   
  
  Mycobacterium bovis BCG, Mycobacterium tuberculosis
  CSDB ID 174784 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: mannan
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: 3318
  Wittkowski M, Mittelstadt J, Brandau S, Reiling N, Lindner B, Torrelles J, Brennan PJ, Holst O "Capsular arabinomannans from Mycobacterium avium with morphotype specific structural differences but identical biological activity" - Journal of Biological Chemistry 282(26) (2007) 19103-19112
  

  The capsules of two colony-morphotypes of Mycobacterium avium strain 2151 were investigated, i.e. of the virulent smooth-transparent (SmT) and the non-virulent smooth-opaque (SmO) type. From both morphotypes we separated a non-acylated arabinomannan (AM) from an acylated polysaccharide fraction by affinity chromatography, of which the AMs were structurally characterised. The AMs from the virulent morphotype in contrast to that from the non-virulent form possessed a larger mannan chain and a shorter arabinan chain. Incubation of murine bone marrow derived macrophages and human dendritic cells showed that the acylated polysaccharide fractions were potent inducers of TNF , IL 12 and IL-10, compared to non-acylated AMs which only led to a marginal cytokine release. Further in vitro experiments showed that both, the acylated polysaccharide fractions as well as the non-acylated AMs were able to induce in vitro anti-tumor cytotoxicity of human peripheral blood mononuclear cells. Thus, morphotype specific structural differences in capsular AMs of M. avium do not correlate with biological activity, however, their acylation is a prerequisite for effective stimulation of murine macrophages and human dendritic cells

  biological activity, Mycobacterium avium, cells, virulent, macrophages, capsules, arabinomannan

  NCBI PubMed ID: 17459879
  Publication DOI: 10.1042/BJ20070017
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: oholst@fz-borstel.de
  Institutions: Immunochemistry and Biochemical Microbiology, Research Center Borstel, Borstel D-23845
  Methods: 13C NMR, 1H NMR, NMR-2D, methylation, SDS-PAGE, chemical analysis, ESI-FTICR-MS, NMR-1D, serological methods
  
   
  
  Mycobacterium avium 2151 SmT
  CSDB ID 21415 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Trivial name: mannan
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_857732,IEDB_857735,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

• Article ID: 3318
  Wittkowski M, Mittelstadt J, Brandau S, Reiling N, Lindner B, Torrelles J, Brennan PJ, Holst O "Capsular arabinomannans from Mycobacterium avium with morphotype specific structural differences but identical biological activity" - Journal of Biological Chemistry 282(26) (2007) 19103-19112
  

  The capsules of two colony-morphotypes of Mycobacterium avium strain 2151 were investigated, i.e. of the virulent smooth-transparent (SmT) and the non-virulent smooth-opaque (SmO) type. From both morphotypes we separated a non-acylated arabinomannan (AM) from an acylated polysaccharide fraction by affinity chromatography, of which the AMs were structurally characterised. The AMs from the virulent morphotype in contrast to that from the non-virulent form possessed a larger mannan chain and a shorter arabinan chain. Incubation of murine bone marrow derived macrophages and human dendritic cells showed that the acylated polysaccharide fractions were potent inducers of TNF , IL 12 and IL-10, compared to non-acylated AMs which only led to a marginal cytokine release. Further in vitro experiments showed that both, the acylated polysaccharide fractions as well as the non-acylated AMs were able to induce in vitro anti-tumor cytotoxicity of human peripheral blood mononuclear cells. Thus, morphotype specific structural differences in capsular AMs of M. avium do not correlate with biological activity, however, their acylation is a prerequisite for effective stimulation of murine macrophages and human dendritic cells

  biological activity, Mycobacterium avium, cells, virulent, macrophages, capsules, arabinomannan

  NCBI PubMed ID: 17459879
  Publication DOI: 10.1042/BJ20070017
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: oholst@fz-borstel.de
  Institutions: Immunochemistry and Biochemical Microbiology, Research Center Borstel, Borstel D-23845
  Methods: 13C NMR, 1H NMR, NMR-2D, methylation, SDS-PAGE, chemical analysis, ESI-FTICR-MS, NMR-1D, serological methods
  
   
  
  Mycobacterium avium 2151 SmO
  CSDB ID 21681 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: lipomannan dodecasaccharide
Contained glycoepitopes: IEDB_130695,IEDB_130701,IEDB_135392,IEDB_136104,IEDB_140116,IEDB_141793,IEDB_141828,IEDB_141829,IEDB_141831,IEDB_143632,IEDB_144983,IEDB_144993,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_534865,IEDB_76933,IEDB_857732,IEDB_857735,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

• Article ID: 3594
  Pozsgay V "Recent developments in synthetic oligosaccharide-based bacterial vaccines" - Current Topics in Medicinal Chemistry 8(2) (2008) 126-140
  

  Synthetic advances made possible chemical assembly of complex oligosaccharide fragments of polysaccharide domains on the surface of human pathogenic bacteria. These oligosaccharides may be recognized by antibodies raised against high molecular weight, native, polysaccharides. In addition to their antigenicity, synthetic oligosaccharides can also function as haptens in their protein conjugates that can elicit not only oligo- but also polysaccharide-specific IgG antibodies in animal models and in humans. A major milestone in the development of new generation vaccines was the demonstration that protein conjugates of synthetic fragments of the capsular polysaccharide of Haemophilus influenzae type b are as efficacious in preventing childhood meningitis and other diseases as is the corresponding licensed commercial vaccine containing the bacterial polysaccharide. The lessons learnt in this and other endeavors described herein are manifold. For example, they teach us about the significance of the oligosaccharide epitope size, the number of their copies per protein in the conjugate, the possible effect of the spacer on anti-saccharide immune response, and the proper choice of the carrier protein combined with the selection of the animal model. The H. influenzae b story also teaches us that that the synthetic approach can be commercially viable.

  Haemophilus influenzae, Streptococcus pneumoniae, Oligosaccharides, Shigella dysenteriae type 1, keyhole limpet hemocyanin, keyhole limpet hemocyanine

  NCBI PubMed ID: 18289082
  Journal NLM ID: 101119673
  Publisher: Bentham Science Publishers
  Correspondence: pozsgayv@mail.nih.gov
  Institutions: National Institute of Child Health and Human Development, National Institutes of Health, 6 Center Dr., MSC 2423, Bethesda, MD 20892-2423, USA
  Methods: chemical synthesis
  
   
  
  Mycobacterium tuberculosis
  CSDB ID 23503 (all data & tools)