Found 30 structures.
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1. Compound ID: 10204
Structure type: fragment of a bigger structure
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_423153,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 4238
Paul G, Wieland F "Sequence of the halobacterial glycosaminoglycan" -
Journal of Biological Chemistry 262 (1987) 9587-9593
The cell-surface glycoprotein of halobacterium contains a sulfated repeating unit saccharide chain, similar to the mammalian glycosaminoglycans. The composition of a presumptive repeating pentasaccharide unit of this glycosaminoglycan is 1 GlcNAc, 1 GalNAc, 1 Gal, 1 GalA (where GalA represents galacturonic acid), 1 3-O-methyl-GalA, and 2 SO42-. Linkage to protein of this glycoconjugate involves the hitherto unique unit Asn-GalNAc, with the N-linked asparagine residue being the second NH2-terminal amino acid and part of the common N-linked glycosyl acceptor sequence Asn-X-Thr(Ser). Transfer of the completed, sulfated glycosaminoglycan from its lipid precursor to the protein occurs at the cell surface, and the presence of this sulfated saccharide chain in the cell-surface glycoprotein seems to be required to maintain the structural integrity of the rod-shaped halobacteria. In this paper, we report the complete saccharide structure of this N-linked glycosaminoglycan. This structure is deduced from chemical analyses of fragments that were isolated after hydrazinolysis and subsequent nitrous acid deamination or after mild acidic hydrolysis of purified Pronase-derived glycosaminoglycan-peptides. The halobacterial glycosaminoglycan consists, on the average, of 10 repeating pentasaccharide units of the following structure. (formula: see text) The reducing end N-acetylgalactosamine residue is linked directly to the asparagine, without a special saccharide linker region.
NCBI PubMed ID: 3597425Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Methods: GLC-MS, gel filtration, partial acid hydrolysis, acid hydrolysis, GLC, deamination, methanolysis, desulfation, hydrazinolysis, reduction, permethylation analysis
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2. Compound ID: 10219
Structure type: oligomer
Compound class: N-glycan
Contained glycoepitopes: IEDB_115136,IEDB_140630,IEDB_142488,IEDB_146664,IEDB_423153,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 2451
Lis H, Sharon N "Protein glycosylation. Structural and functional aspects" -
European Journal of Biochemistry 218 (1993) 1-27
During the last decade, there have been enormous advances in our knowledge of glycoproteins and the stage has been set for the biotechnological production of many of them for therapeutic use. These advances are reviewed, with special emphasis on the structure and function of the glycoproteins (excluding the proteoglycans). Current methods for structural analysis of glycoproteins are surveyed, as are novel carbohydrate-peptide linking groups, and mono- and oligo-saccharide constituents found in these macromolecules. The possible roles of the carbohydrate units in modulating the physicochemical and biological properties of the parent proteins are discussed, and evidence is presented on their roles as recognition determinants between molecules and cells, or cell and cells. Finally, examples are given of changes that occur in the carbohydrates of soluble and cell-surface glycoproteins during differentiation, growth and malignancy, which further highlight the important role of these substances in health and disease.
NCBI PubMed ID: 8243456Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Membrane Research and Biophysics, Weizmann Institute of Science, Rehovot, Israel
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3. Compound ID: 11926
|
a-Galp-(1-4)-a-GlcpA-(1-4)-+
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D-gro-a-D-manHepp-(1-3)-a-D-Manp-(1-2)-L-gro-a-D-manHepp-(1-5)-a-Kdop
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L-gro-a-D-manHepp-(1-7)-+ |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_115136,IEDB_130650,IEDB_130701,IEDB_136906,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983930,SB_44,SB_67,SB_7,SB_72
The structure is contained in the following publication(s):
- Article ID: 4760
Jones MD, Vinogradov E, Nomellini JF, Smit J "The core and O-polysaccharide structure of the Caulobacter crescentus lipopolysaccharide" -
Carbohydrate Research 402 (2015) 111-117
Here we describe the analysis of the structure of the lipopolysaccharide (LPS) from Caulobacter crescentus strain JS1025, a derivative of C. crescentus CB15 NA1000 with an engineered amber mutation in rsaA, leading to the loss of the protein S-layer and gene CCNA_00471 encoding a putative GDP-l-fucose synthase. LPS was isolated using an aqueous membrane disruption method. Polysaccharide and core oligosaccharide were produced by mild acid hydrolysis and analyzed by nuclear magnetic resonance spectroscopy and chemical methods. Spectra revealed the presence of two polysaccharides, one of them, a rhamnan, could be removed using periodate oxidation. Another polymer, built from 4-amino-4-deoxy-d-rhamnose (perosamine), mannose, and 3-O-methyl-glucose, should be the O-chain of the LPS according to genetic data. The attribution of the rhamnan as a part of LPS or a separate polymer was not possible.
Lipopolysaccharide, nuclear magnetic resonance, extracellular polysaccharides, Caulobacter crescentus
NCBI PubMed ID: 25498010Publication DOI: 10.1016/j.carres.2014.10.003Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: J. Smit
Institutions: National Research Council of Canada, 100 Sussex Drive, Building Sussex, Room 3079, Ottawa, Ontario K1A 0R6, Canada, Department of Microbiology and Immunology, 2350 Health Sciences Mall, Life Sciences Centre, University of British Columbia, Vancouver, BC V6T 1Z3, Canada
Methods: 13C NMR, 1H NMR, methylation, periodate oxidation, gel filtration, NMR-2D, GC-MS, SDS-PAGE, sugar analysis, TLC, 31P NMR, acid hydrolysis, mild acid hydrolysis, NMR-1D, reduction with NaBD4, de-N-acylation
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4. Compound ID: 17626
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b-Xyl-(1-2)-+
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b-GlcA-(1-2)-+ |
| |
b-Xyl-(1-2)-+ | |
| | |
-3)-a-Man-(1-3)-a-Man-(1-3)-a-Man-(1-
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b-Xyl-(1-4)-+ |
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Structure type: structural motif or average structure
Compound class: glucuronoxylomannan
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_115576,IEDB_130701,IEDB_1394182,IEDB_140116,IEDB_140630,IEDB_144983,IEDB_145668,IEDB_152206,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_2270799,IEDB_423153,IEDB_76933,IEDB_983930,SB_197,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 6926
Doering TL "A unique alpha-1,3 mannosyltransferase of the pathogenic fungus Cryptococcus neoformans" -
Journal of Bacteriology 181 (1999) 5482-5488
The major virulence factor of the pathogenic fungusCryptococcus neoformans is an extensive polysaccharide capsule which surrounds the cell. Almost 90% of the capsule is composed of a partially acetylated linear α-1,3-linked mannan substituted with D-xylose and D-glucuronic acid. A novel mannosyltransferase with specificity appropriate for a role in the synthesis of this glucuronoxylomannan is active in cryptococcal membranes. This membrane-associated activity transfers mannose in vitro from GDP-mannose to an α-1,3-dimannoside acceptor, forming a second α-1,3 linkage. Product formation by the transferase is dependent on protein, time, temperature, divalent cations, and each substrate. It is not affected by amphomycin or tunicamycin but is inhibited by GDP and mannose-1-phosphate. The described activity is not detectable in the model yeast Saccharomyces cerevisiae, consistent with the absence of a similar polysaccharide structure in that organism. A second mannosyltransferase from C. neoformans membranes adds mannose in α-1,2 linkage to the same dimannoside acceptor. The two activities differ in pH optimum and cation preference. While the α-1,2 transferase does not have specificity appropriate for a role in glucuronoxylomannan synthesis, it may participate in production of mannoprotein components of the capsule. This study suggests two new targets for antifungal drug discovery.
Journal NLM ID: 2985120RWWW link: http://jb.asm.org/content/181/17/5482.longPublisher: American Society for Microbiology
Correspondence: doering@borcim.wustl.edu
Institutions: Department of Pharmacology, Cornell University Medical College, New York, New York
Methods: enzymatic digestion, enzymatic assay, radiolabelling
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5. Compound ID: 17676
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b-Manp-(1-4)-a-GlcpA-(1-2)-+
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a-Glcp-(1-2)-+ |
| |
-6)-b-Galf-(1-6)-b-Galf-(1- |
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Structure type: polymer chemical repeating unit
Contained glycoepitopes: IEDB_115136,IEDB_136095,IEDB_137472,IEDB_137485,IEDB_1394182,IEDB_140630,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_149176,IEDB_152206,IEDB_190606,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_72
The structure is contained in the following publication(s):
- Article ID: 6949
Ahrazem O, Prieto A, Gomez-Miranda B, Bernabé M, Leal JA "Comparison of cell-wall polysaccharides from Nectria cinnabarina with those from the group of Nectria with Sesquicillium anamorphs" -
Microbiology 147 (2001) 1839-1849
Alkali-extractable and water-soluble polysaccharides were purified from cell walls of five species of Sesquicillium or its teleomorphs, Nectria lasiacidis and Nectria impariphialis, and from Nectria cinnabarina, the type species of Nectria, a heterogeneous genus that belongs to the Hypocreales. Methylation and NMR analyses for determination of linkage types and structure were performed and indicated differences between the polysaccharides purified during the present study and those isolated from other nectrioid fungi, namely the presence of 5-O-substituted galactofuranose (→5)-Galf-(1→) in the main chain together with 2,6-di-O-substituted galactofuranose (→2,6)-Galf-(1→) residues in Sesquicillium buxi and Sesquicillium pseudosetosum. The polysaccharide from N. impariphialis was similar to those obtained from the above species, although an additional residue of 6-O-substituted glucopyranose (→6)-Glcp-(1→), was detected in some side chains. In N. lasiacidis and Sesquicillium candelabrum the polysaccharide contained an additional branching point of 5,6-di-O-substituted galactofuranose (→5,6)-Galf-(1→) linked to terminal N-acetylglucosamine GlcNAc-(1→). These chains were linked to a small mannan core. All these polysaccharides showed major differences to the polysaccharide of N. cinnabarina, which was formed by a main chain of (1→6)-β-linked galactofuranose units almost fully branched at positions 2-O by either single residues of glucopyranose or acidic chains containing glucuronic acid and mannose.
chemotaxonomy, complex galactans, Hypocreales
Journal NLM ID: 0376646WWW link: http://mic.sgmjournals.org/content/147/7/1839.abstractPublisher: Washington, DC: Kluwer Academic/Plenum Publishers
Correspondence: aleal@cib.csic.es
Institutions: Centro de Investigaciones Biológicas, CSIC, Velázquez 144, 28006-Madrid, Spain, Instituto de Quı́mica Orgánica, Departamento de Quı́mica Orgánica Biológica, CSIC, Juan de la Cierva 3, 28006-Madrid, Spain
Methods: 13C NMR, 1H NMR, GLC-MS, IR, acid hydrolysis, GLC, methanolysis, HPLC, TOCSY, NOESY, HMQC-TOCSY
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6. Compound ID: 17730
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b-Xyl-(1-2)-+
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b-GlcA-(1-2)-+ |
| |
b-Xyl-(1-2)-+ | |
| | |
-3)-a-Man-(1-3)-a-Man-(1-3)-a-Man-(1-
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b-Xyl-(1-4)-+ |
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Structure type: suggested polymer biological repeating unit
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_115576,IEDB_130701,IEDB_1394182,IEDB_140116,IEDB_140630,IEDB_144983,IEDB_145668,IEDB_152206,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_2270799,IEDB_423153,IEDB_76933,IEDB_983930,SB_197,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 6961
Bar-Peled M, Griffith CL, Doering TL "Functional cloning and characterization of a UDP-glucuronic acid decarboxylase: the pathogenic fungus Cryptococcus neoformans elucidates UDP-xylose synthesis" -
Proceedings of the National Academy of Sciences of the USA 21 (2001) 12003-12008
UDP-xylose is a sugar donor required for the synthesis of diverse and important glycan structures in animals, plants, fungi, and bacteria. Xylose-containing glycans are particularly abundant in plants and in the polysaccharide capsule that is the major virulence factor of the pathogenic fungus Cryptococcus neoformans. Biosynthesis of UDP-xylose is mediated by UDP-glucuronic acid decarboxylase, which converts UDP-glucuronic acid to UDP-xylose. Although this enzymatic activity was described over 40 years ago it has never been fully purified, and the gene encoding it has not been identified. We used homology to a bacterial gene, hypothesized to encode a related function, to identify a cryptococcal sequence as putatively encoding a UDP-glucuronic acid decarboxylase. A soluble 47-kDa protein derived from bacteria expressing the C. neoformans gene catalyzed conversion of UDP-glucuronic acid to UDP-xylose, as confirmed by NMR analysis. NADH, UDP, and UDP-xylose inhibit the activity. Close homologs of the cryptococcal gene, which we termed UXS1, appear in genome sequence data from organisms ranging from bacteria to humans.
Publication DOI: 10.1073/pnas.211229198Journal NLM ID: 7505876Publisher: National Academy of Sciences
Correspondence: peled@ccrc.uga.edu
Institutions: Complex Carbohydrate Research Center and Department of Botany, University of Georgia, Athens, GA 30602, USA, Department of Molecular Microbiology, Washington University School of Medicine, St. Louis, MO 63110, USA
Methods: 1H NMR, SDS-PAGE, HPLC, cloning, protein expression, UDP-GlcA decarboxylase assay
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7. Compound ID: 18020
Structure type: monomer
Compound class: glycoglycerolipid
Contained glycoepitopes: IEDB_115136,IEDB_140630
The structure is contained in the following publication(s):
- Article ID: 7063
Fontaine T, Lamarre C, Simenel C, Lambou K, Coddeville B, Delepierre M, Latge JP "Characterization of glucuronic acid containing glycolipid in Aspergillus fumigatus mycelium" -
Carbohydrate Research 344(15) (2009) 1960-1967
A glucuronic acid containing glycerolipid was isolated from the filamentous fungi Aspergillus fumigatus. This acidic glycolipid was extracted from the membrane of mycelium and purified by two successive chromatographic steps on DEAE-Sephadex and Silica columns. Chemical structural analysis was performed using methylation, gas-chromatography, gas-chromatography-mass spectrometry, nano-electrospray mass spectrometry and (1)H/(13)C NMR spectra. The corresponding structure is a 3-(O-α-glucuronyl)-1,2-diacyl-sn-glycerol, where acyl chains are mainly C(16:0), C(18:0), C(18:1), and C(18:2). This α-GlcA-diacylglycerol is not present in fungal conidia. This acidic glycerolipid is described here for the first time in a fungal species. Two homologs of UDP-glucose dehydrogenase that convert UDP-glucose into UDP-glucuronic acid, are present in A. fumigatus genome, UGD1 and UGD2. Gene deletion showed that only UGD1 is essential for the biosynthesis of GlcA-DG. However, no particular phenotype has been observed in the Ugd1Delta mutant. Biological function of this acidic glycolipid remains unknown in A. fumigatus.
glucuronic acid, UDP-Glucose dehydrogenase, glycerolipid, Aspergillus fumigatus
NCBI PubMed ID: 19709651Publication DOI: 10.1016/j.carres.2009.07.012Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Thierry Fontaine
Institutions: Unité des Aspergillus, Institut Pasteur, Paris, France, Unité de Résonance Magnétique Nucléaire des Biomolécules, CNRS URA 2185, Institut Pasteur, Paris, France, Laboratoire de Glycobiologie Structurale et Fonctionnelle, UMR 8576 CNRS, Université des sciences et Technologies de Lille Flandres-Artois, Villeneuve d’Ascq, France, CHUQ—Pav. St-François d’Assise, Centre de recherche, Québec, Québec, Canada
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, PCR, GC-MS, DNA techniques, ESI-MS, GC, composition analysis, methanolysis, genetic methods, extraction, HPTLC
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8. Compound ID: 18186
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b-Xylp-(1-2)-+
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b-Xylp-(1-2)-+ |
| |
b-GlcpA-(1-2)-+ | |
| | |
-3)-a-Manp-(1-3)-a-Manp-(1-3)-a-Manp-(1-
| |
b-Xylp-(1-4)-+ b-Xylp-(1-4)-+ |
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Structure type: suggested polymer biological repeating unit
Compound class: CPS, glucuronoxylomannan (GXM)
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_115576,IEDB_130701,IEDB_1394182,IEDB_140116,IEDB_140630,IEDB_144983,IEDB_145668,IEDB_152206,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_2270799,IEDB_423153,IEDB_76933,IEDB_983930,SB_197,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 7125
McFadden DC, Fries BC, Wang F, Casadevall A "Capsule structural heterogeneity and antigenic variation in Cryptococcus neoformans" -
Eukaryotic Cell 6(8) (2007) 1464-1473
Cryptococcus neoformans is a human pathogenic fungus with a capsule composed primarily of glucuronoxylomannan (GXM) that is important for virulence. Current views of GXM structure postulate a polymer composed of repeating mannose trisaccharide motifs bearing a single β(1,2) glucuronic acid with variable xylose and O-acetyl substitutions to form six triads. GXM from different strains is notoriously variable in triad composition, but it is not known if the polymer consists of one or more motif-repeating units. We investigated the polymeric organization of GXM by using mass spectrometry to determine if its compositional motif arrangement was similar to that of bacterial capsular polysaccharides, namely, a polymer of a single repeating unit. The results were consistent with, and confirmatory for, the current view that the basic unit of GXM is a repeating mannose trisaccharide motif, but we also found evidence for the copolymerization of different GXM repeating units in one polysaccharide molecule. Analysis of GXM from isogenic phenotypic switch variants suggested structural differences caused by glucuronic acid positional effects, which implied flexibility in the synthetic pathway. Our results suggest that cryptococcal capsule synthesis is fundamentally different from that observed in prokaryotes and employs a unique eukaryotic approach, which theoretically could synthesize an infinite number of structural combinations. The biological significance of this capsule construction scheme is that it is likely to confer a powerful avoidance strategy for interactions with the immune system and phagocytic environmental predators. Consistent with this premise, the antigenic variation of a capsular epitope recognized by a nonprotective antibody was observed under different growth conditions.
biosynthesis, antibodies, infection, polysaccharide capsule, Glucuronoxylomannan
Publication DOI: 10.1128/EC.00162-07Journal NLM ID: 101130731Publisher: American Society for Microbiology
Correspondence: Arturo Casadevall
Institutions: Department of Medicine, Division of Infectious Disease, Department of Microbiology and Immunology, Laboratory for Macromolecular Analysis and Proteomics, Albert Einstein College of Medicine, Bronx, New York 10461
Methods: 1H NMR, partial acid hydrolysis, TLC, ESI-MS, acid hydrolysis, MS/MS, electrophoresis, HPLC, light scattering, viscosity measurement
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9. Compound ID: 18187
|
b-GlcpA-(1-2)-+ b-Xylp-(1-2)-+
| |
-3)-a-Manp-(1-3)-a-Manp-(1-3)-a-Manp-(1-
| |
b-Xylp-(1-4)-+ b-Xylp-(1-4)-+ |
Show graphically |
Structure type: suggested polymer biological repeating unit
Compound class: CPS, glucuronoxylomannan (GXM)
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_115576,IEDB_130701,IEDB_1394182,IEDB_140116,IEDB_140630,IEDB_144983,IEDB_145668,IEDB_152206,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_423153,IEDB_76933,IEDB_983930,SB_197,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 7125
McFadden DC, Fries BC, Wang F, Casadevall A "Capsule structural heterogeneity and antigenic variation in Cryptococcus neoformans" -
Eukaryotic Cell 6(8) (2007) 1464-1473
Cryptococcus neoformans is a human pathogenic fungus with a capsule composed primarily of glucuronoxylomannan (GXM) that is important for virulence. Current views of GXM structure postulate a polymer composed of repeating mannose trisaccharide motifs bearing a single β(1,2) glucuronic acid with variable xylose and O-acetyl substitutions to form six triads. GXM from different strains is notoriously variable in triad composition, but it is not known if the polymer consists of one or more motif-repeating units. We investigated the polymeric organization of GXM by using mass spectrometry to determine if its compositional motif arrangement was similar to that of bacterial capsular polysaccharides, namely, a polymer of a single repeating unit. The results were consistent with, and confirmatory for, the current view that the basic unit of GXM is a repeating mannose trisaccharide motif, but we also found evidence for the copolymerization of different GXM repeating units in one polysaccharide molecule. Analysis of GXM from isogenic phenotypic switch variants suggested structural differences caused by glucuronic acid positional effects, which implied flexibility in the synthetic pathway. Our results suggest that cryptococcal capsule synthesis is fundamentally different from that observed in prokaryotes and employs a unique eukaryotic approach, which theoretically could synthesize an infinite number of structural combinations. The biological significance of this capsule construction scheme is that it is likely to confer a powerful avoidance strategy for interactions with the immune system and phagocytic environmental predators. Consistent with this premise, the antigenic variation of a capsular epitope recognized by a nonprotective antibody was observed under different growth conditions.
biosynthesis, antibodies, infection, polysaccharide capsule, Glucuronoxylomannan
Publication DOI: 10.1128/EC.00162-07Journal NLM ID: 101130731Publisher: American Society for Microbiology
Correspondence: Arturo Casadevall
Institutions: Department of Medicine, Division of Infectious Disease, Department of Microbiology and Immunology, Laboratory for Macromolecular Analysis and Proteomics, Albert Einstein College of Medicine, Bronx, New York 10461
Methods: 1H NMR, partial acid hydrolysis, TLC, ESI-MS, acid hydrolysis, MS/MS, electrophoresis, HPLC, light scattering, viscosity measurement
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10. Compound ID: 18188
Structure type: suggested polymer biological repeating unit
Compound class: CPS, glucuronoxylomannan (GXM)
Contained glycoepitopes: IEDB_115136,IEDB_115576,IEDB_130701,IEDB_1394182,IEDB_140116,IEDB_140630,IEDB_144983,IEDB_152206,IEDB_164174,IEDB_423153,IEDB_76933,IEDB_983930,SB_197,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 7125
McFadden DC, Fries BC, Wang F, Casadevall A "Capsule structural heterogeneity and antigenic variation in Cryptococcus neoformans" -
Eukaryotic Cell 6(8) (2007) 1464-1473
Cryptococcus neoformans is a human pathogenic fungus with a capsule composed primarily of glucuronoxylomannan (GXM) that is important for virulence. Current views of GXM structure postulate a polymer composed of repeating mannose trisaccharide motifs bearing a single β(1,2) glucuronic acid with variable xylose and O-acetyl substitutions to form six triads. GXM from different strains is notoriously variable in triad composition, but it is not known if the polymer consists of one or more motif-repeating units. We investigated the polymeric organization of GXM by using mass spectrometry to determine if its compositional motif arrangement was similar to that of bacterial capsular polysaccharides, namely, a polymer of a single repeating unit. The results were consistent with, and confirmatory for, the current view that the basic unit of GXM is a repeating mannose trisaccharide motif, but we also found evidence for the copolymerization of different GXM repeating units in one polysaccharide molecule. Analysis of GXM from isogenic phenotypic switch variants suggested structural differences caused by glucuronic acid positional effects, which implied flexibility in the synthetic pathway. Our results suggest that cryptococcal capsule synthesis is fundamentally different from that observed in prokaryotes and employs a unique eukaryotic approach, which theoretically could synthesize an infinite number of structural combinations. The biological significance of this capsule construction scheme is that it is likely to confer a powerful avoidance strategy for interactions with the immune system and phagocytic environmental predators. Consistent with this premise, the antigenic variation of a capsular epitope recognized by a nonprotective antibody was observed under different growth conditions.
biosynthesis, antibodies, infection, polysaccharide capsule, Glucuronoxylomannan
Publication DOI: 10.1128/EC.00162-07Journal NLM ID: 101130731Publisher: American Society for Microbiology
Correspondence: Arturo Casadevall
Institutions: Department of Medicine, Division of Infectious Disease, Department of Microbiology and Immunology, Laboratory for Macromolecular Analysis and Proteomics, Albert Einstein College of Medicine, Bronx, New York 10461
Methods: 1H NMR, partial acid hydrolysis, TLC, ESI-MS, acid hydrolysis, MS/MS, electrophoresis, HPLC, light scattering, viscosity measurement
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11. Compound ID: 18233
|
/Variants 0/-+
|
/Variants 1/-+ |
| |
-3)-a-Man-(1-3)-a-Man-(1-3)-a-Man-(1-
|
b-GlcA-(1-2)-+
/Variants 0/ is:
b-Man-(1-4)-b-Xyl-(1-6)-
OR (exclusively)
b-Man-(1-4)-b-Xyl-(1-4)-b-Xyl-(1-6)-
/Variants 1/ is:
b-Man-(1-4)-b-Xyl-(1-6)-
OR (exclusively)
b-Man-(1-4)-b-Xyl-(1-4)-b-Xyl-(1-6)- |
Show graphically |
Structure type: structural motif or average structure
Compound class: CPS, glucuronoxylomannan (GXM)
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_115576,IEDB_130701,IEDB_137485,IEDB_1394182,IEDB_140116,IEDB_140630,IEDB_144983,IEDB_152206,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_423153,IEDB_76933,IEDB_983930,SB_197,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 7134
Schutzbach J, Ankel H, Brockhausen I "Synthesis of cell envelope glycoproteins of Cryptococcus laurentii" -
Carbohydrate Research 342(7) (2007) 881-893
Fungi of the genus Cryptococcus are encapsulated basidiomycetes that are ubiquitously found in the environment. These organisms infect both lower and higher animals. Human infections that are common in immune-compromised individuals have proven difficult to cure or even control with currently available antimycotics that are quite often toxic to the host. The virulence of Cryptococcus has been linked primarily to its polysaccharide capsule, but also to cell-bound glycoproteins. In this review, we show that Cryptococcus laurentii is an excellent model for studies of polysaccharide and glycoprotein synthesis in the more pathogenic relative C. neoformans. In particular, we will discuss the structure and biosynthesis of O-linked carbohydrates on cell envelope glycoproteins of C. laurentii. These O-linked structures are synthesized by at least four mannosyltransferases, two galactosyltransferases, and at least one xylosyltransferase that have been characterized. These glycosyltransferases have no known homologues in human tissues. Therefore, enzymes involved in the synthesis of cryptococcal glycoproteins, as well as related enzymes involved in capsule synthesis, are potential targets for the development of specific inhibitors for treatment of cryptococcal disease.
synthesis, galactosyltransferase, sugar nucleotides, Mannosyltransferase, Cryptococcus neoformans, Cryptococcus laurentii, O-Linked glycoprotein synthesis, Xylosyltransferase, AIDS
NCBI PubMed ID: 17316583Publication DOI: 10.1016/j.carres.2007.01.002Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Inka.JSBach@kos.net (John Schutzbach)
Institutions: Department of Medicine and Department of Biochemistry, Queen’s University, Etherington Hall, Kingston, Ontario, Canada, Service de Virologie, Hôpital Saint-Vincent-de-Paul, Faculté de Médecine, Université René Descartes, Paris, France
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12. Compound ID: 18264
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b-Xylp-(1-2)-+
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b-Xylp-(1-2)-+ |
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b-GlcpA-(1-2)-+ | |
| | |
-3)-a-D-Manp-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1- |
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Structure type: polymer chemical repeating unit
Trivial name: glucuronoxylomannan (GXM)
Compound class: CPS
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_115576,IEDB_130701,IEDB_140116,IEDB_140630,IEDB_144983,IEDB_145668,IEDB_152206,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_2270799,IEDB_423153,IEDB_76933,IEDB_983930,SB_197,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 7145
McFadden D, Zaragoza O, Casadevall A "The capsular dynamics of Cryptococcus neoformans" -
Trends in Microbiology 14(11) (2006) 497-505
Cryptococcus neoformans is a soil-dwelling fungus that causes life-threatening illness in immunocompromised individuals and latently infects many healthy individuals. C. neoformans, unlike other human pathogenic fungi, is surrounded by a polysaccharide capsule that is essential for survival and enables C. neoformans to thwart the mammalian immune system. The capsule is a dynamic structure that undergoes changes in size and rearranges during budding. Here, the latest information and unresolved questions regarding capsule synthesis, structure, assembly, growth and rearrangements are discussed along with the concept that self-assembly is important in capsular dynamics.
virulence, polysaccharide capsule, Cryptococcus neoformans, Glucuronoxylomannan
NCBI PubMed ID: 17114598Publication DOI: 10.1016/j.tim.2006.09.003Journal NLM ID: 9310916Publisher: Cambridge: Elsevier Trends Journals
Correspondence: Casadevall A
Institutions: Department of Medicine, Division of Infectious Disease, Albert Einstein College of Medicine, Bronx, NY, USA, Microbiology and Immunology, Albert Einstein College of Medicine, Bronx, NY, USA, Servicio de Micología, Centro Nacional de Microbiología, Instituto de Salud Carlos III, Madrid, Spain, Northeast Biodefense Center, Department of Epidemiology, Columbia University, New York, NY, USA
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13. Compound ID: 18265
|
b-Xylp-(1-2)-+
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b-Xylp-(1-2)-+ |
| |
b-GlcpA-(1-2)-+ | |
| | |
-3)-a-D-Manp-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-
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b-Xylp-(1-4)-+ |
Show graphically |
Structure type: suggested polymer biological repeating unit
Trivial name: glucuronoxylomannan (GXM)
Compound class: CPS
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_115576,IEDB_130701,IEDB_140116,IEDB_140630,IEDB_144983,IEDB_145668,IEDB_152206,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_2270799,IEDB_423153,IEDB_76933,IEDB_983930,SB_197,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 7145
McFadden D, Zaragoza O, Casadevall A "The capsular dynamics of Cryptococcus neoformans" -
Trends in Microbiology 14(11) (2006) 497-505
Cryptococcus neoformans is a soil-dwelling fungus that causes life-threatening illness in immunocompromised individuals and latently infects many healthy individuals. C. neoformans, unlike other human pathogenic fungi, is surrounded by a polysaccharide capsule that is essential for survival and enables C. neoformans to thwart the mammalian immune system. The capsule is a dynamic structure that undergoes changes in size and rearranges during budding. Here, the latest information and unresolved questions regarding capsule synthesis, structure, assembly, growth and rearrangements are discussed along with the concept that self-assembly is important in capsular dynamics.
virulence, polysaccharide capsule, Cryptococcus neoformans, Glucuronoxylomannan
NCBI PubMed ID: 17114598Publication DOI: 10.1016/j.tim.2006.09.003Journal NLM ID: 9310916Publisher: Cambridge: Elsevier Trends Journals
Correspondence: Casadevall A
Institutions: Department of Medicine, Division of Infectious Disease, Albert Einstein College of Medicine, Bronx, NY, USA, Microbiology and Immunology, Albert Einstein College of Medicine, Bronx, NY, USA, Servicio de Micología, Centro Nacional de Microbiología, Instituto de Salud Carlos III, Madrid, Spain, Northeast Biodefense Center, Department of Epidemiology, Columbia University, New York, NY, USA
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14. Compound ID: 18266
|
b-Xylp-(1-2)-+
|
b-Xylp-(1-2)-+ |
| |
b-GlcpA-(1-2)-+ | |
| | |
-3)-a-D-Manp-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1-
| |
b-Xylp-(1-4)-+ b-Xylp-(1-4)-+ |
Show graphically |
Structure type: suggested polymer biological repeating unit
Trivial name: glucuronoxylomannan (GXM)
Compound class: CPS
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_115576,IEDB_130701,IEDB_140116,IEDB_140630,IEDB_144983,IEDB_145668,IEDB_152206,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_2270799,IEDB_423153,IEDB_76933,IEDB_983930,SB_197,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 7145
McFadden D, Zaragoza O, Casadevall A "The capsular dynamics of Cryptococcus neoformans" -
Trends in Microbiology 14(11) (2006) 497-505
Cryptococcus neoformans is a soil-dwelling fungus that causes life-threatening illness in immunocompromised individuals and latently infects many healthy individuals. C. neoformans, unlike other human pathogenic fungi, is surrounded by a polysaccharide capsule that is essential for survival and enables C. neoformans to thwart the mammalian immune system. The capsule is a dynamic structure that undergoes changes in size and rearranges during budding. Here, the latest information and unresolved questions regarding capsule synthesis, structure, assembly, growth and rearrangements are discussed along with the concept that self-assembly is important in capsular dynamics.
virulence, polysaccharide capsule, Cryptococcus neoformans, Glucuronoxylomannan
NCBI PubMed ID: 17114598Publication DOI: 10.1016/j.tim.2006.09.003Journal NLM ID: 9310916Publisher: Cambridge: Elsevier Trends Journals
Correspondence: Casadevall A
Institutions: Department of Medicine, Division of Infectious Disease, Albert Einstein College of Medicine, Bronx, NY, USA, Microbiology and Immunology, Albert Einstein College of Medicine, Bronx, NY, USA, Servicio de Micología, Centro Nacional de Microbiología, Instituto de Salud Carlos III, Madrid, Spain, Northeast Biodefense Center, Department of Epidemiology, Columbia University, New York, NY, USA
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15. Compound ID: 18267
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b-GlcpA-(1-2)-+ b-Xylp-(1-2)-+
| |
-3)-a-D-Manp-(1-3)-a-D-Manp-(1-3)-a-D-Manp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: glucuronoxylomannan (GXM)
Compound class: CPS
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_115576,IEDB_130701,IEDB_140116,IEDB_140630,IEDB_144983,IEDB_145668,IEDB_152206,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_423153,IEDB_76933,IEDB_983930,SB_197,SB_44,SB_67,SB_72
The structure is contained in the following publication(s):
- Article ID: 7145
McFadden D, Zaragoza O, Casadevall A "The capsular dynamics of Cryptococcus neoformans" -
Trends in Microbiology 14(11) (2006) 497-505
Cryptococcus neoformans is a soil-dwelling fungus that causes life-threatening illness in immunocompromised individuals and latently infects many healthy individuals. C. neoformans, unlike other human pathogenic fungi, is surrounded by a polysaccharide capsule that is essential for survival and enables C. neoformans to thwart the mammalian immune system. The capsule is a dynamic structure that undergoes changes in size and rearranges during budding. Here, the latest information and unresolved questions regarding capsule synthesis, structure, assembly, growth and rearrangements are discussed along with the concept that self-assembly is important in capsular dynamics.
virulence, polysaccharide capsule, Cryptococcus neoformans, Glucuronoxylomannan
NCBI PubMed ID: 17114598Publication DOI: 10.1016/j.tim.2006.09.003Journal NLM ID: 9310916Publisher: Cambridge: Elsevier Trends Journals
Correspondence: Casadevall A
Institutions: Department of Medicine, Division of Infectious Disease, Albert Einstein College of Medicine, Bronx, NY, USA, Microbiology and Immunology, Albert Einstein College of Medicine, Bronx, NY, USA, Servicio de Micología, Centro Nacional de Microbiología, Instituto de Salud Carlos III, Madrid, Spain, Northeast Biodefense Center, Department of Epidemiology, Columbia University, New York, NY, USA
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