Show legend Show as text

Structure type: oligomer
Trivial name: mannosyl-phosphatidyl-myo-inositol (MPI) anchor
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141795,IEDB_141830,IEDB_141834,IEDB_143632,IEDB_144983,IEDB_144993,IEDB_152206,IEDB_164480,IEDB_76933,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72

• Article ID: 491
  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: 15304754
  Publication DOI: 10.1385/abab:118:1-3:253
  Journal NLM ID: 8208561
  Publisher: 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
  
   
  
  Mycobacterium tuberculosis
  CSDB ID 9205 (all data & tools)

Show legend Show as text

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

• Article ID: 491
  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: 15304754
  Publication DOI: 10.1385/abab:118:1-3:253
  Journal NLM ID: 8208561
  Publisher: 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
  
   
  
  Mycobacterium tuberculosis, Mycobacterium bovis BCG, Mycobacterium leprae
  CSDB ID 31634 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: mannopentaose
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_137485,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

• Article ID: 824
  Ilg T, Craik D, Currie G, Multhaup G, Bacic A "Stage-specific proteophosphoglycan from Leishmania mexicana antastigotes - Structural characterization of novel mono-, di-, and triphosphorylated phosphodiester-linked oligosaccharides" - Journal of Biological Chemistry 273(22) (1998) 13509-13523
  

  Intracellular amastigotes of the protozoan parasite Leishmania mexicana secrete a macromolecular proteo-phosphoglycan (aPPG) into the phagolysosome of their host cell, the mammalian macrophage. The structures of aPPG glycans were analyzed by a combination of high pH anion exchange high pressure liquid chromatography, gas chromatography-mass spectrometry, enzymatic digestions, electrospray-mass spectrometry as well as 1H and 31P NMR spectroscopy. Some glycans are identical to oligosaccharides known from Leishmania mexicana promastigote lipophosphoglycan and secreted acid phosphatase. However, the majority of the aPPG glycans represent amastigote stage-specific and novel structures. These include neutral glycans ( [Glc(bl-3)(n=1-2)]Gal(bl-4)Man, Gal(bl-3)Gal(bl-4)Man, Gal(bl-3)Glc(bl-3)Gal(bl-4)Man ), several monophosphorylated glycans containing the conserved phosphodisaccharide backbone (R-3-[PO4-6-Gal] (bl-4)Man) but carrying stage-specific modifications ( R = Gal(bl-,[Glc(bl-3)(n=1-2)Glc(bl- ), and monophosphorylated aPPG tri- and tetrasaccharides that are uniquely phosphorylated on the terminal hexose ( PO4-6-Glc(bl-3)Gal(bl-4)Man, PO4-6-Glc(bl-3)Glc(bl-3)Gal(bl-4)Man, PO4-6-Gal(bl-3)Glc(bl-3)Gal(b1-4)Man ). In addition aPPG contains highly unusual di- and triphosphorylated glycans whose major species are PO4-6-Glc(bl-3)Glc(bl-3)[PO4-6-Gal](bl-4)Man, PO4-6-Gal(bl-3)Glc(b1-3)[PO4-6-Gal](bl-4)Man, PO4-6-Gal(bl-3)Glc(bl-3)Glc(bl-3)[PO4-6-Gal](bl-4)Man, PO4-6-Glc(bl-3)[PO4-6-Glc](bl-3)[PO4-6-Gal](b1-4)Man, PO4-6-Gal(bl-3)[PO4-6-Glc](bl-3)Glc(bl-3)[PO4-6-Gal](bl-4)Man, and PO4-6-Glc(bl-3)[PO4-6-Glc](bl-3)Glc(bl-3)[PO4-6-Gal](bl-4)Man. These glycans are linked together by the conserved phosphodiester R-Man-(a1-PO4-6)-Gal-R or the novel phosphodiester R-Man-(a1-PO4-6)-Glc-R and are connected to Ser(P) of the protein backbone most likely via the linkage R-Man-(a1-PO4-Ser). The variety of stage-specific glycan structures in Leishmania mexicana aPPG suggests the presence of developmentally regulated amastigote glycosyl-transferases which may be potential anti-parasite drug targets.

  oligosaccharide, structural, characterization, Oligosaccharides, leishmania

  NCBI PubMed ID: 9593686
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: thomas.ilg@tuebingen.mpg.de
  Institutions: Plant Cell Biology Research Centre, School of Botany, University of Melbourne, Victoria 3052, Australia, Walter and Eliza Hall Institute of Medical Research, P.O. Royal Melbourne Hospital, Victoria 3050, Australia, the Centre for Drug Design and Development, University of Queensland, Brisbane, Queensland 4072, Australia, Centre for Molecular Biology, Heidelberg, Germany
  Methods: NMR-2D, GC-MS, ESI-MS, enzymatic digestion, HPAE-HPLC
  
   
  
  Leishmania mexicana
  CSDB ID 2571 (all data & tools)
• Article ID: 6395
  Ogawa K, Matsuda K, Tamari K, Kiyo-oka S "Studies on the glucomannan from Candida utilis. Part III. Immunochemical analysis of the glucomannan from Candida utilis" - Agricultural and Biological Chemistry 54 (1990) 593-597
  

  A glucomannan isolated from a Candida utilis mutant having a new chemotype was further studied by inhibition of the homologous precipitin reaction with oligosaccharides obtained from the glucomannan by partial acid hydrolysis and controlled acetolysis. Oligosaccharides having at least two consecutive α-(1----2)-linked mannose residues at the non-reducing end and gluco-manno-pentasaccharide were effective inhibitors. Thus, it appears that the glucomannan had two groups of antigenic determinants, one corresponding to the side chains of two, three, and four mannose units connected by α-(1----2)-linkage, and the other corresponding to a side chain composed of an O-α-D-glucopyranosyl-(1----6)-O-α-D-mannopyranosyl- (1----2)-O-α-D-mannopyranosyl-(1----2)-D-mannose unit. These results support a probable structure of repeating units for the glucomannan presented previously. The relative susceptibility of intersaccharidic linkages to acid hydrolysis in the mannan is discussed.

  NCBI PubMed ID: 1368530
  Journal NLM ID: 0370452
  Publisher: Tokyo: Agricultural Chemical Society Of Japan
  Institutions: Department of Fundamental Science, College of Science and Engineering, Iwaki Meisei University, Fukushima, Japan
  Methods: acid hydrolysis, precipitin reaction
  
   
  
  Candida utilis
  CSDB ID 101335 (all data & tools)
• Article ID: 6478
  Kobayashi H, Shibata N, Suzuki S "Evidence for oligomannosyl residues containing both b-1,2 and a-1,2 linkages as a serotype A-specific epitope(s) in mannans of Candida albicans" - Infection and Immunity 60 (1992) 2106-2109
  

  In order to identify the branches containing both β-1,2 and α-1,2 linkages as the serotype A-specific epitope(s) in the mannans of Candida albicans, serotype A strains with oligosaccharides constituting the β-1,2 linkage, the α-1,2 linkage, and both the β-1,2 and the α-1,2 linkages were prepared from the mannans of C. albicans serotype A strains (NIH A-207 and J-1012) and tested for their inhibitory effects in the precipitin and slide agglutination assays. The results indicated that two oligosaccharides containing both β-1,2 and α-1,2 linkages, Manp β-1-2Manp α 1-2Manp α 1-2Manp α 1-2Man and Manp β-1-2Manp β-1-2Manp α 1-2Manp α 1-2Manp α 1-2Man, served as epitopes participating in the serotype A specificity of C. albicans strains.

  NCBI PubMed ID: 1373405
  Journal NLM ID: 0246127
  Publisher: American Society for Microbiology
  Institutions: Second Department of Hygienic Chemistry, Tohoku College of Pharmacy, Miyagi, Japan
  Methods: enzymatic digestion, acetolysis, partial acid degradation
  
   
  
  Candida albicans A NIH A-207, Candida albicans A NIH J-1012
  CSDB ID 130427 (all data & tools)
• Article ID: 6529
  Kobayashi H, Kojimahara T, Takahashi K, Takikawa M, Takahashi SI, Shibata N, Okawa Y, Suzuki S "Structural determination of D-mannans of pathogenic yeasts Candida stellatoidea Type I strains: TIMM 0310 and ATCC 11006 compared to IFO 1397" - Carbohydrate Research 214 (1991) 131-145
  

  The structures of the cell-wall D-mannans of pathogenic yeasts of Candida stellatoidea Type I strains, IFO 1397, TIMM 0310, and ATCC 11006, were investigated by mild acid and, alkaline hydrolysis, by digestion with the Arthrobacter GJM-1 strain exo-α-D-mannosidase, and by acetolysis. The modified D-mannans and their degradation products were studied by 1H- and 13C-n.m.r. analyses. D-Manno-oligosaccharides released by acid treatment from the parent D-mannans were identified as the homologous β-(1----2)-linked D-manno-oligosaccharides from biose to hexaose, whereas those obtained by alkaline degradation were the homologous α-(1----2)-linked D-mannobiose and D-mannotriose. The acid- and alkali-modified D-mannans lacking 1H-n.m.r. signals above 4.900 p.p.m. [corresponding to β-(1----2)-linked D-mannopyranose units] were acetolyzed with 10:10:1 (v/v) Ac2O-AcOH-H2SO4, and the resultant D-manno-oligosaccharides were also analyzed. It was found that the longest branches of these D-mannans, corresponding to hexaosyl residues, had the following structures: α-D-manp-(1----3)-α-D-manp-(1----2)-α-D-manp+ ++-(1----2)-α-D-manp- (1----2)-α-D-manp-(1----2)-D-Man and α-D-manp-(1----2)-α-D-manp-(1----3)-α-D-manp+ ++-(1----2)-α-D-manp- (1----2)-α-D-manp-(1----2)-D-Man. These results indicate that the D-mannans of C. stellatoidea Type I strains possess structures in common with the D-mannans of Candida albicans serotype B strain (see ref. 4) containing phosphate-bound β-(1----2)-linked oligo-D-mannosyl residues.

  NCBI PubMed ID: 1954627
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Second Department of Hygienic Chemistry, Tohoku College of Pharmacy, Miyagi, Japan, Second Department of Hygienic Chemistry, Tohoku College of Pharmacy, Miyagi, Japan.
  Methods: gel filtration, 13C NMR, 1H NMR, enzymatic digestion, acetolysis, slide-agglutination reaction, acid and alkaline hydrolysis
  
   
  
  Candida stellatoidea I IFO 1397
  CSDB ID 116244 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_137485,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

• Article ID: 824
  Ilg T, Craik D, Currie G, Multhaup G, Bacic A "Stage-specific proteophosphoglycan from Leishmania mexicana antastigotes - Structural characterization of novel mono-, di-, and triphosphorylated phosphodiester-linked oligosaccharides" - Journal of Biological Chemistry 273(22) (1998) 13509-13523
  

  Intracellular amastigotes of the protozoan parasite Leishmania mexicana secrete a macromolecular proteo-phosphoglycan (aPPG) into the phagolysosome of their host cell, the mammalian macrophage. The structures of aPPG glycans were analyzed by a combination of high pH anion exchange high pressure liquid chromatography, gas chromatography-mass spectrometry, enzymatic digestions, electrospray-mass spectrometry as well as 1H and 31P NMR spectroscopy. Some glycans are identical to oligosaccharides known from Leishmania mexicana promastigote lipophosphoglycan and secreted acid phosphatase. However, the majority of the aPPG glycans represent amastigote stage-specific and novel structures. These include neutral glycans ( [Glc(bl-3)(n=1-2)]Gal(bl-4)Man, Gal(bl-3)Gal(bl-4)Man, Gal(bl-3)Glc(bl-3)Gal(bl-4)Man ), several monophosphorylated glycans containing the conserved phosphodisaccharide backbone (R-3-[PO4-6-Gal] (bl-4)Man) but carrying stage-specific modifications ( R = Gal(bl-,[Glc(bl-3)(n=1-2)Glc(bl- ), and monophosphorylated aPPG tri- and tetrasaccharides that are uniquely phosphorylated on the terminal hexose ( PO4-6-Glc(bl-3)Gal(bl-4)Man, PO4-6-Glc(bl-3)Glc(bl-3)Gal(bl-4)Man, PO4-6-Gal(bl-3)Glc(bl-3)Gal(b1-4)Man ). In addition aPPG contains highly unusual di- and triphosphorylated glycans whose major species are PO4-6-Glc(bl-3)Glc(bl-3)[PO4-6-Gal](bl-4)Man, PO4-6-Gal(bl-3)Glc(b1-3)[PO4-6-Gal](bl-4)Man, PO4-6-Gal(bl-3)Glc(bl-3)Glc(bl-3)[PO4-6-Gal](bl-4)Man, PO4-6-Glc(bl-3)[PO4-6-Glc](bl-3)[PO4-6-Gal](b1-4)Man, PO4-6-Gal(bl-3)[PO4-6-Glc](bl-3)Glc(bl-3)[PO4-6-Gal](bl-4)Man, and PO4-6-Glc(bl-3)[PO4-6-Glc](bl-3)Glc(bl-3)[PO4-6-Gal](bl-4)Man. These glycans are linked together by the conserved phosphodiester R-Man-(a1-PO4-6)-Gal-R or the novel phosphodiester R-Man-(a1-PO4-6)-Glc-R and are connected to Ser(P) of the protein backbone most likely via the linkage R-Man-(a1-PO4-Ser). The variety of stage-specific glycan structures in Leishmania mexicana aPPG suggests the presence of developmentally regulated amastigote glycosyl-transferases which may be potential anti-parasite drug targets.

  oligosaccharide, structural, characterization, Oligosaccharides, leishmania

  NCBI PubMed ID: 9593686
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: thomas.ilg@tuebingen.mpg.de
  Institutions: Plant Cell Biology Research Centre, School of Botany, University of Melbourne, Victoria 3052, Australia, Walter and Eliza Hall Institute of Medical Research, P.O. Royal Melbourne Hospital, Victoria 3050, Australia, the Centre for Drug Design and Development, University of Queensland, Brisbane, Queensland 4072, Australia, Centre for Molecular Biology, Heidelberg, Germany
  Methods: NMR-2D, GC-MS, ESI-MS, enzymatic digestion, HPAE-HPLC
  
   
  
  Leishmania mexicana
  CSDB ID 2572 (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_141793,IEDB_141795,IEDB_141830,IEDB_141834,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_164174,IEDB_164480,IEDB_76933,IEDB_983930,SB_136,SB_196,SB_197,SB_198,SB_44,SB_67,SB_72,SB_77

• Article ID: 1598
  Yamane K, Yamanaka T, Yamamoto N, Furukawa T, Fukushima H, Walker CB, Leung KP "A novel exopolysaccharide from a clinical isolate of Prevotella nigrescens: purification, chemical characterization and possible role in modifying human leukocyte phagocytosis" - Oral Microbiology and Immunology 20(1) (2005) 1-9
  

  Yamane K, Yamanaka T, Yamamoto N, Furukawa T, Fukushima H, Walker CB, Leung K-P. A novel exopolysaccharide from a clinical isolate of Prevotella nigrescens: purification, chemical characterization and possible role in modifying human leukocyte phagocytosis. Oral Microbiol Immunol 2005: 20: 1-9. (c) Blackwell Munksgaard, 2005. Prevotella nigrescens, a gram-negative black-pigmented anaerobic rod, has frequently been isolated from periodontitis and periapical periodontitis lesions. We have isolated an exopolysaccharide-producing P. nigrescens, strain 22, from a chronic periodontitis lesion. The purpose of this study was to determine the chemical composition and function of the exopolysaccharide associated with this clinical isolate. The chemical composition and structure of the purified exopolysaccharide from strain 22 were determined by high performance liquid chromatography and methylation analysis. To define the biological function of this exopolysaccharide, a chemically induced exopolysaccharide nonproducing mutant, strain 328, which was derived from strain 22, was established. The biological effects of exopolysaccharide were determined by comparing the ability of strain 22, strain 328 or heat-killed strain 22 to form abscesses in mice and to interfere with the phagocytic activity of peripheral blood polymorphonuclear leukocytes. Chemical analysis showed that isolated exopolysaccharide consisted of mannose (521.6 mug/mg), glucose (25.6 mug/mg), fructose (65.8 mug/mg), galactose (12.5 mug/mg), arabinose (6.2 mug/mg), xylose (3.2 mug/mg), rhamnose (6.1 mug/mg), and ribose (0.6 mug/mg). Methylation analysis of exopolysaccharide indicated that the linkages of mannose were primarily (1→2, 1→6) (1→2) (1→6), and (1→3). Strain 22 and, to a lesser extent, its heat-killed counterpart induced greater abscess formation in mice than strain 328, even though the enzymatic profile of strain 22 was similar to that of strain 328. The ability of strain 328 to induce abscess formation was restored by adding the purified exopolysaccharide isolated from strain 22 to the cell suspension of strain 328. Exopolysaccharide alone failed to induce abscess formation in mice. Further, strain 328 but not the untreated or heat-killed strain 22, was phagocytosed by polymorphonuclear leukocytes both in the presence and in the absence of opsonic factors. The results suggest that these polysaccharides isolated from strain 22, which primarily consisted of mannose, may play a key role in the development of the chronic inflammatory lesion from which this strain was isolated

  structure, blood, clinical, human, isolate, role, strain, characterization, polysaccharide, methylation analysis, analysis, polysaccharides, cell, form, factor, high, induced, mice, mutant, biological, linkage, exopolysaccharide, activity, chemical, methylation, enzymatic, ribose, arabinose, function, Gram-negative, abscess, formation, composition, glucose, purified, rhamnose, galactose, chromatography, Japan, fructose, effect, ability, phagocytosis, Mannose, purification, opsonic, liquid chromatography, bacteriology, absence, development, oral, Xylose, profile, anaerobic, chemically induced, inflammatory, leukocyte, periodontitis, polymorphonuclear, polymorphonuclear leukocyte, Prevotella, rod

  NCBI PubMed ID: 15612938
  Journal NLM ID: 8707451
  Publisher: Copenhagen: Munksgaard
  Institutions: Department of Bacteriology, Osaka Dental University, Osaka, Japan, Periodontal Disease Research Clinic, College of Dentistry, University of Florida, Gainesville, FL, Microbiology Branch, U.S. Army Dental Research Detachment, Walter Reed Army Institute of Research, Great Lakes, IL, USA
  Methods: methylation, sugar analysis
  
   
  
  Prevotella nigrescens 22
  CSDB ID 10194 (all data & tools)

Show legend Show as text

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

• 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 10731 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen, CPS
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

• Article ID: 1777
  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: 7533007
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
  
   
  
  Acetobacter methanolicus MB135
  CSDB ID 108588 (all data & tools)
• Article ID: 2291
  Grimmecke HD, Voges M, Knirel YA, Shashkov AS, Lauk W, Kiesel B "Structure of the capsular polysaccharide and the O-side-chain of the lipopolysaccharide from Acetobacter methanolicus MB 135 (IMET 11402)" - Carbohydrate Research 253 (1994) 283-286
  
  Journal NLM ID: 0043535
  Publisher: Elsevier
  
   
  
  Acetobacter methanolicus MB135
  CSDB ID 117634 (all data & tools)
• Article ID: 5791
  Knirel YA, Van Calsteren M "Bacterial exopolysaccharides" - Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2021) 1-75
  

  Bacterial extracellular polysaccharides are known as a cell-bound capsule, a sheath, or a slime, which is excreted into the environment. They play an important role in virulence of medical bacteria and plant-to-symbiont interaction and are used for serotyping of bacteria and production of vaccines. Some exopolysaccharides have commercial applications in industry, and claims of health benefits have been documented for an increasing number of them. Exopolysaccharides have diverse composition and structure, and some contain sugar and non-sugar components that are found in bacterial carbohydrates only. The present article provides an updated collection of the data on exopolysaccharides of various classes of gram-negative and gram-positive bacteria reported until the end of 2019. When known, biosynthesis pathways of exopolysaccharides are treated in a summary manner. References are made to structure and biosynthesis relatedness between exopolysaccharides of different bacterial taxa as well as between bacterial polysaccharides and mammalian glycosaminoglycans.

  polysaccharide structure, Gram-negative bacteria, capsule, Biofilm, polysaccharide biosynthesis, gram-positive bacteria, Monosaccharide composition, Bacterial exopolysaccharide, non-sugar component

  Publication DOI: 10.1016/B978-0-12-819475-1.00005-5
  Publisher: Elsevier
  Correspondence: marie-rose.vancalsteren@canada.ca; yknirel@gmail.com
  Editors: Barchi J, Kamerling H
  Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Saint-Hyacinthe Research and Development Centre, Agriculture and Agri-Food Canada, Saint-Hyacinthe, QC, Canada
  
   
  
  Acidomonas methanolica MB 135
  CSDB ID 6977 (all data & tools)

Show legend Show as text

Structure type: polymer chemical repeating unit ; n=2-6
Trivial name: mannan
Compound class: EPS
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

• Article ID: 3396
  Herasimenka Y, Cescutti P, Impallomeni G, Rizzo R "Exopolysaccharides produced by Inquilinus limosus, a new pathogen of cystic fibrosis patients: novel structures with usual components" - Carbohydrate Research 342(16) (2007) 2404-2415
  

  The major cause of morbidity and mortality in patients with cystic fibrosis, an autosomal recessive disorder, is chronic microbial colonisation of the major airways that leads to exacerbation of pulmonary infection. Several different microbes colonise cystic fibrosis lungs, and Pseudomonas aeruginosa is one of the most threatening, since the establishment of mucoid (alginate producing) strains is ultimately associated with the patient's death. Very recently a new bacterium, named Inquilinus limosus, was repeatedly found infecting the respiratory tract of cystic fibrosis patients. Its multi-resistance characteristic to antibiotics might result in the spreading of I. limosus infection among the cystic fibrosis community, as recently happened with strains of the Burkholderia cepacia complex. Since exopolysaccharides are recognised as important virulence factors in lung infections, the primary structure of the polysaccharide produced by I. limosus strain LMG 20952(T) was investigated as the first step in understanding its role in pathogenesis. The structure was determined by means of methylation analysis, acid degradations, mass spectrometry and NMR spectroscopy. The results showed that the bacterium produced a mixture constituted of the following polymers:Both polymers were completely substituted with pyruvyl ketal groups, a novel structural characteristic not previously found in bacterial polysaccharides. The absolute configuration of all pyruvyl groups was S. Inspection of possible local conformations assumed by the two polysaccharide chains showed features, which might provide interesting clues for understanding structure-function relationships

  NMR, structure, exopolysaccharide, cystic fibrosis, Inquilinus limosus, ESIMS, xopolysaccharide

  NCBI PubMed ID: 17719019
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: pcescutti@units.it
  Institutions: Dipartimento di Biochimica Biofisica e Chimica delle Macromolecole, Università di Trieste, via L. Giorgieri 1, I-34127 Trieste, Italy
  Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, GC-MS, ESI-MS, GLC, composition analysis, NMR-1D, ozonolysis, acid degradation
  
   
  
  Inquilinus limosus LMG 20952T
  CSDB ID 21952 (all data & tools)

Show legend Show as text

Structure type: structural motif or average structure
Trivial name: cell-surface mannan
Contained glycoepitopes: IEDB_130701,IEDB_131173,IEDB_133966,IEDB_133967,IEDB_134618,IEDB_136104,IEDB_137485,IEDB_140116,IEDB_141793,IEDB_141795,IEDB_141828,IEDB_141829,IEDB_141830,IEDB_141831,IEDB_141832,IEDB_141833,IEDB_141834,IEDB_143632,IEDB_144983,IEDB_144995,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_1539315,IEDB_164480,IEDB_173895,IEDB_76920,IEDB_76933,IEDB_857732,IEDB_857735,IEDB_858578,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

• Article ID: 3844
  Ferreira JA, Azevedo NF, Vieira MJ, Figueiredo C, Goodfellow BJ, Monteiro MA, Coimbra MA "Identification of cell-surface mannans in a virulent Helicobacter pylori strain" - Carbohydrate Research 345(6) (2010) 830-838
  

  With the intent of contributing to a carbohydrate-based vaccine against the gastroduodenal pathogen, Helicobacter pylori, we report here the structure of cell-surface mannans obtained from a virulent strain. Unlike other wild-type strains, this strain was found to express in good quantities this polysaccharide in vitro. Structural analysis revealed a branched mannan formed by a backbone of α-(1→6)-linked mannopyranosyl residues with approximately 80% branching at the O-2 position. The branches were composed of O-2-linked Man residues in both α- and β-configurations: [abstract: see text]. In addition, this strain also expressed cell-surface emblematic H. pylori lipopolysaccharides (LPS) containing partially fucosylated polyLacNAc O-chains. Affinity assays with polymyxin-B and concanavalin A revealed no association between the mannan and the LPS. The described mannans may be implicated in the mediation of host-microbial interactions and immunological modulation.

  Lipopolysaccharide, Helicobacter pylori, vaccine, mannan, cell-surface glycans

  NCBI PubMed ID: 20227685
  Publication DOI: 10.1016/j.carres.2010.01.022
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: mac@ua.pt
  Institutions: Departamento de Química, Universidade de Aveiro, Aveiro, Portugal, LEPAE, Department of Chemical Engineering, Faculty of Engineering, University of Porto, Porto, Portugal, Centro de Engenharia Biológica, Universidade do Minho, Campus de Gualtar, Braga, Portugal, Institute of Molecular Pathology and Immunology, University of Porto, Portugal, Medical Faculty of Porto, Porto, Portugal, CICECO, University of Aveiro, Aveiro, Portugal, Department of Chemistry, University of Guelph, Guelph, ON, Canada
  Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR, composition analysis, affinity chromatography
  
   
  
  Helicobacter pylori 968
  CSDB ID 25245 (all data & tools)

Show legend Show as text

Structure type: homopolymer
Compound class: EPS
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

• Article ID: 4341
  Kuttel M, Ravenscroft N, Foschiatti M, Cescutti P, Rizzo R "Conformational properties of two exopolysaccharides produced by Inquilinus limosus, a cystic fibrosis lung pathogen" - Carbohydrate Research 350 (2012) 40-48
  

  Inquilinus limosus is a multi-resistant bacterium found in the respiratory tract of patients with cystic fibrosis. This bacterium produces two unique fully pyruvylated exopolysaccharides in similar quantities: an α-(1→2)-linked mannan and a β-(1→3)-linked glucan. We employed molecular modelling methods to probe the characteristic conformations and dynamics of these polysaccharides, with corroboration from potentiometric titrations and circular dichroism experiments. Our calculations reveal different structural motifs for the mannan and glucan polysaccharides: the glucan forms primarily right-handed helices with a wide range of extensions, while the mannan forms only left-handed helices. This finding is supported by our circular dichroism experiments. Our calculations also show that the (1→3)-β-D-Glcp linkage is more dynamically flexible than the (1→2)-α-D-Manp: the glucan characteristically forms a range of wide helices with large central cavities. In contrast, the mannan forms rigid regular 'bottlebrush' helices with a minimal central cavity. The widely different character of these two polymers suggests a possible differentiation of biological roles.

  molecular modelling, carbohydrates, conformation analysis, Inquilinus limosus, Lung opportunists, Bacterial exopolysaccharides

  NCBI PubMed ID: 22261278
  Publication DOI: 10.1016/j.carres.2011.12.025
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: M. Kuttel
  Institutions: Department of Chemistry, University of Cape Town, Rondebosch 7701, South Africa, Department of Computer Science, University of Cape Town, Rondebosch 7701, South Africa, Department of Life Sciences, University of Trieste, Via Licio Giorgieri 1, 34127 Trieste, Italy
  Methods: conformation analysis, MD simulations, molecular modeling, CD
  
   
  
  Inquilinus limosus LMG 20952T
  CSDB ID 28443 (all data & tools)

Show legend Show as text

Structure type: structural motif or average structure
Trivial name: D-arabino-D-mannan
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141793,IEDB_141795,IEDB_141828,IEDB_141829,IEDB_141830,IEDB_141831,IEDB_141834,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_164480,IEDB_76933,IEDB_857732,IEDB_857735,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

• Article ID: 4430
  Ovodov YS "Bacterial capsular antigens. Structural patterns of capsular antigens" - Biochemistry (Moscow) 71(9) (2006) 937-954
  

  Structural patterns of bacterial capsular antigens including capsular polysaccharides and exoglycans are given in this review. In addition, the immunological activity of capsular antigens and their role in type specificity of bacteria are discussed.

  structure, capsular polysaccharides, bacterial capsular antigens, bacterial exoglycans, immunological activity, type specificity

  NCBI PubMed ID: 17009947
  Publication DOI: 10.1134/S000629790609001X
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Correspondence: ovoys@physiol.komisc.ru
  Institutions: Institute of Physiology, Komi Science Center, Urals Branch of the Russian Academy of Sciences, Syktyvkar 167982, Russia
  
   
  
  Mycobacterium tuberculosis
  CSDB ID 28729 (all data & tools)

Show legend Show as text

Structure type: homopolymer ; n=35-40
Compound class: O-polysaccharide
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

• Article ID: 5078
  Komaniecka I, Choma A, Zamlynska K, Sroka-Bartnicka A, Sowinski P "Structure of O-specific polysaccharide of Oligotropha carboxidovorans OM5 - a wastewater bacterium" - Carbohydrate Research 439 (2017) 30-34
  

  Oligotropha carboxidovorans strain OM5 (previously known as Pseudomonas carboxydovorans OM5) is a rod-shaped Gram-negative bacterium isolated from wastewater. This bacterium is able to live in aerobic and, facultatively, in autotrophic conditions. For autotrophic growth, the bacteria can utilize carbon monoxide or hydrogen as a source of energy. The O-specific polysaccharide isolated from O. carboxidovorans OM5 lipopolysaccharide was structurally characterized using chemical analyses, 1D and 2D NMR spectroscopy, and MALDI-TOF mass spectrometry techniques. The polysaccharide was found to be a homopolymer built up of 3-O-methyl-α-d-mannose residues linked by (1 → 2)-glycosidic bonds. The degree of polymerization of high-molecular-weight polysaccharide was estimated at approximately 35-40 units. The structure of the homopolymer is depicted below: [Formula: see text].

  Lipopolysaccharide, O-specific polysaccharide, 3-O-methylmannose, Oligotropha carboxidovorans

  NCBI PubMed ID: 28088676
  Publication DOI: 10.1016/j.carres.2017.01.001
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: iwona.komaniecka@poczta.umcs.lublin.pl
  Institutions: Department of Genetics and Microbiology, Maria Curie-Sklodowska University, Lublin, Poland, Intercollegiate NMR Laboratory, Department of Chemistry, Gdansk University of Technology, Poland
  
   
  
  Oligotropha carboxidovorans OM5
  CSDB ID 12010 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycoinositol phospholipid
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141795,IEDB_141830,IEDB_141834,IEDB_143632,IEDB_144983,IEDB_144993,IEDB_152206,IEDB_164480,IEDB_534865,IEDB_76933,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72

• Article ID: 5688
  Patil PS, Cheng TJ, Zulueta MM, Yang ST, Lico LS, Hung SC "Total synthesis of tetraacylated phosphatidylinositol hexamannoside and evaluation of its immunomodulatory activity" - Nature Communications 6 (2015) ID 7239
  

  Tuberculosis, aggravated by drug-resistant strains and HIV co-infection of the causative agent Mycobacterium tuberculosis, is a global problem that affects millions of people. With essential immunoregulatory roles, phosphatidylinositol mannosides are among the cell-envelope components critical to the pathogenesis and survival of M. tuberculosis inside its host. Here we report the first synthesis of the highly complex tetraacylated phosphatidylinositol hexamannoside (Ac2PIM6), having stearic and tuberculostearic acids as lipid components. Our effort makes use of stereoelectronic and steric effects to control the regioselective and stereoselective outcomes and minimize the synthetic steps, particularly in the key desymmetrization and functionalization of myo-inositol. A short synthesis of tuberculostearic acid in six steps from the Roche ester is also described. Mice exposed to the synthesized Ac2PIM6 exhibit increased production of interleukin-4 and interferon-γ, and the corresponding adjuvant effect is shown by the induction of ovalbumin- and tetanus toxoid-specific antibodies

  synthesis, Mycobacterium tuberculosis, Ac2PIM6, phosphatidylinositolmannoside

  NCBI PubMed ID: 26037164
  Publication DOI: 10.1038/ncomms8239
  Journal NLM ID: 101528555
  Publisher: London: Nature Publishing Group
  Correspondence: Hung SC
  Institutions: Genomics Research Center, Academia Sinica, Taipei, Taiwan
  Methods: ELISA, chemical synthesis, biological assays, immunological assays, cytokine production
  
   
  
  Mycobacterium tuberculosis
  CSDB ID 49321 (all data & tools)

Show legend Show as text

Structure type: structural motif or average structure ; 51330
Compound class: EPS
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141793,IEDB_141795,IEDB_141829,IEDB_141830,IEDB_141832,IEDB_141833,IEDB_141834,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_146664,IEDB_152206,IEDB_153220,IEDB_164480,IEDB_76933,IEDB_983930,IEDB_983931,SB_136,SB_191,SB_192,SB_196,SB_198,SB_44,SB_67,SB_72

• Article ID: 5768
  Gan L, Li X, Zhang H, Zhang R, Wang H, Xu Z, Peng B, Tian Y "Preparation, characterization and functional properties of a novel exopolysaccharide produced by the halophilic strain Halomonas saliphila LCB169T" - International Journal of Biological Macromolecules 156 (2020) 372-380
  

  A novel exopolysaccharide, designated hsEPS, was successfully prepared from the high-salt-fermented broth of a novel species Halomonas saliphila LCB169T by ethanol precipitation, anion-exchange and gel-filtration chromatography, and its structure was well-characterized by means of chemical and spectral analyses. Results showed that hsEPS was primarily composed of mannose and glucose with a relative weight-average molecular weight of 5.133 × 104 g/mol. It was deduced that the major backbone contained (1→2)-linked α-D-Manp and (1→6)-linked α-D-Manp with branches substituted at C-2 by T-α-D-Manp and at C-6 by the fragment of T-α-D-Manp-(1→2)-α-D-Manp-(1→. A sheet-like structure was observed under high magnification. The water solubility index, water holding capacity, oil holding capacity and foaming capacity of hsEPS were 98.0, 19.3, 1386.7 and 82.2%, respectively. It also exhibited outstanding emulsifying activity against all tested edible oils. Together, the resulted data indicated that hsEPS might serve as an active ingredient in food, cosmetics and detergents.

  structure, exopolysaccharide, halophiles, Functional properties, Halomonas saliphila

  NCBI PubMed ID: 32289411
  Publication DOI: 10.1016/j.ijbiomac.2020.04.062
  Journal NLM ID: 7909578
  Publisher: Butterworth-Heinemann
  Correspondence: pengbiyu@scu.edu.cn; yqtian@scu.edu.cn
  Institutions: College of Biomass Science and Engineering, Sichuan University, Chengdu 610065, PR China, Key Laboratory of Leather Chemistry and Engineering (Sichuan University), Ministry of Education, Chengdu 610065, PR China
  Methods: gel filtration, 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, sugar analysis, FTIR, HPAEC-PAD, SEM, HPSEC-RI-MALLS, WSI, WHC, OHC
  
   
  
  Halomonas saliphila LCB169(T)
  CSDB ID 32101 (all data & tools)

Show legend Show as text

Structure type: homopolymer
Trivial name: sulfated mannan
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

• Article ID: 5797
  Kokoulin MS, Lizanov IN, Romanenko LA, Chikalovets IV "Structure of phosphorylated and sulfated polysaccharides from lipopolysaccharide of marine bacterium Marinicella litoralis KMM 3900(T)" - Carbohydrate Research 490 (2020) 107961
  

  Two polysaccharide fractions were obtained by mild acid degradation of the lipopolysaccharide of the marine bacterium Marinicella litoralis KMM 3900T. The major polysaccharide was found to contain glycerol 1-phosphate (PGro) and methyl phosphate substituents (PMe), and the following structure of its disaccharide repeating unit was established by sugar analysis, dephosphorylation, Smith degradation, and 1D and 2D NMR spectroscopy: →4)-α-L-Rhap2PGro(~40%)-(1→3)-β-D-Manp6PMe(~80%)-(1 →. The minor polysaccharide was shown to consist of 4-O-sulfate-D-mannopyranosyl residues, non-stoichiometric methylated at O-3 and acetylated at O-6: →2)-α-D-Manp3R4S6Ac(~75%)-(1→, where R is Me (85%) or H (15%).

  Lipopolysaccharide, polysaccharide, Marine bacterium, methyl phosphate, 3-O-Methyl-D-mannose, Marinicella litoralis

  NCBI PubMed ID: 32120020
  Publication DOI: 10.1016/j.carres.2020.107961
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: maxchem@mail.ru
  Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of Russian Academy of Sciences, Prospekt 100 let Vladivostoku 159, Vladivostok, 690022, Russia, Far Eastern Federal University, Ul. Sukhanova 8, 690950, Vladivostok, Russia
  Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, SDS-PAGE, sugar analysis, 31P NMR, ESI-MS, anion-exchange chromatography, GC, Smith degradation, de-O-acetylation, FTIR, GPC, HF treatment
  
   
  
  Marinicella litoralis KMM 3900(T)
  CSDB ID 5065 (all data & tools)