Found 213 structures.
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1. Compound ID: 199
Structure type: polymer chemical repeating unit
Trivial name: glucan
Compound class: EPS, cell wall polysaccharide
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158538,IEDB_232584,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 48
Dueñas-Chasco MT, Rodríguez-Carvajal MA, Tejero-Mateo P, Espartero JL, Irastorza-Iribas A, Gil-Serrano AM "Structural analysis of the exopolysaccharides produced by Lactobacillus spp. G-77" -
Carbohydrate Research 307(1-2) (1998) 125-133
The exopolysaccharide produced by a ropy strain of Lactobacillus spp. G-77 in a semi-defined medium, was found to be a mixture of two homopolymers composed of D-Glc. The two poly-saccharides were separated and, on the basis of monosaccharide and methylation analyses, 1H, 13C, 1D and 2D NMR experiments, one of the polysaccharides was shown to be a 2-substituted-(1-3)-β-D-glucan, identical to that described for the EPS from Pediococcus damnosus 2.6 (M.T. Duenas-Chasco, M.A. Rodriguez-Carvajal, P. Tejero-Mateo, G. Franco-Rodriguez, J. L. Espartero, A. Irastorza-Iribar, and A.M. Gil-Serrano, Carbohydr. Res., 303 (1997) 453-458), and the other polysaccharide was shown to consist of repeating units with the following structure [formula: see text]
repeating unit, exopolysaccharide, Lactobacillus spp. G-77
NCBI PubMed ID: 9658568Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Departamento de Quimica Aplicada, Facultad de Ciencias Quimicas, Universidad del Pais Vasco, San Sebastian, Spain, Departamento de Quimica Organica, Universidad del Sevillia, Sevillia, Spain, Departamento de Quimica Organica y Farmaceutica, Facultad de Farmacia, Universidad del Sevillia, Sevillia, Spain
Methods: NMR-2D, methylation, NMR, sugar analysis
- Article ID: 3809
Zdorovenko EL, Kachala VV, Sidarenka AS, Izhik AV, Kisileva EP, Shashkov AS, Novik GI, Knirel YA "Structure of the cell-wall polysaccharides of probiotic bifidobacteria Bifidobacterium bifidum BIM B-465" -
Carbohydrate Research 344(17) (2009) 2417-2420
The composition and structure of cell wall polysaccharides of a biotechnologically promising probiotic strain of bifidobacteria Bifidobacteriumbifidum BIM B-465 were established by monosaccharide and methylation analyses along with 2D (1)H-(1)H homonuclear and (1)H-(13)C heteronuclear correlation NMR spectroscopy. The major polysaccharide represents a branched glucogalactan consisting of heptasaccharide repeating units having the following structure: →6)-α-D-Glcp-(1→3)-β-D-Galf-(1→3)-α-D-Glcp-(1→2)-β-D-Galf-(1→3)-α-D-Galp-(1→3)-α-D-Glcp-(1→ [structure: see the text]. The second isolated polysaccharide is a branched glucan with the main chain of (1→6)-linked α-D-glucopyranose residues, approximately 60% of which are 2-substituted with a single α-D-glucopyranosyl group. This polysaccharide is a characteristic of various microorganisms, including some lactobacteria studied earlier.
structure, cell wall polysaccharide, glucogalactan, Bifidobacterium bifidum, probiotic polysaccharide
NCBI PubMed ID: 19804881Publication DOI: 10.1016/j.carres.2009.08.039Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evelina@mail.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, sugar analysis, GLC, NMR-1D
- Article ID: 5832
Pyclik M, Srutkova D, Schwarzer M, Gorska S "Bifidobacteria cell wall-derived exo-polysaccharides, lipoteichoic acids, peptidoglycans, polar lipids and proteins - their chemical structure and biological attributes" -
International Journal of Biological Macromolecules 147 (2020) 333-349
A variety of health benefits has been documented to be associated with the consumption of probiotic bacteria, namely bifidobacteria and lactobacilli. Thanks to the scientific advances in recent years we are beginning to understand the molecular mechanisms by which bacteria in general and probiotic bacteria in particular act as host physiology and immune system modulators. More recently, the focus has shifted from live bacteria towards bacteria-derived defined molecules, so called postbiotics. These molecules may represent safer alternative compared to the live bacteria while retaining the desired effects on the host. The excellent source of effector macromolecules is the bacterial envelope. It contains compounds that are pivotal in the adhesion phenomenon, provide direct bacteria-to-host signaling capacity and the associated physiological impact and immunomodulatory properties of bacteria. Here we comprehensively review the structure and biological role of Bifidobacterium surface and cell wall molecules: exopolysaccharides, cell wall polysaccharides, lipoteichoic acids, polar lipids, peptidoglycans and proteins. We discuss their involvement in direct signaling to the host cells and their described immunomodulatory effects.
exopolysaccharide, Bacterial antigens, Bifidobacterium, peptidoglycan, lipoteichoic acid, probiotics
NCBI PubMed ID: 31899242Publication DOI: 10.1016/j.ijbiomac.2019.12.227Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: schwarzer@biomed.cas.cz; sabina.gorska@hirszfeld.pl
Institutions: Laboratory of Microbiome Immunobiology, Hirszfeld Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland, Laboratory of Gnotobiology, Institute of Microbiology of the Czech Academy of Sciences, Novy Hradek, Czech Republic
- Article ID: 5880
De Vuyst L, De Vin F "Exopolysaccharides from Lactic Acid Bacteria" -
Book: Comprehensive Glycoscience: From Chemistry to Systems Biology. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering (2007) 477-519
carbohydrates, polysaccharides, Lactic acid bacteria, exopolysaccharides, glycolipids, glycoproteins, Glycomics
Publication DOI: 10.1016/B978-044451967-2/00129-XPublisher: Elsevier
Correspondence: ldvuyst@vub.ac.be
Editors: Barchi J, Kamerling H
Institutions: Department of Applied Biological Sciences and Engineering, Research Group of Industrial Microbiology and Food Biotechnology, Vrije Universiteit Brussel, Brussels, Belgium
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2. Compound ID: 216
|
a-L-Fuc-(1-3)-b-D-GlcpNAc-(1-7)-+
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{{{-a-D-Glcp-(1-6)-}}}a-D-Glcp-(1-2)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo |
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Structure type: oligomer
Contained glycoepitopes: IEDB_130650,IEDB_135813,IEDB_136045,IEDB_137340,IEDB_140088,IEDB_141807,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144998,IEDB_145669,IEDB_146664,IEDB_150092,IEDB_151531,IEDB_152214,IEDB_158538,IEDB_174333,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_192,SB_86
The structure is contained in the following publication(s):
- Article ID: 53
Edwards NJ, Monteiro MA, Walsh EJ, Moran AP, Roberts IS, High NJ "Lewis X structures in the O antigen side-chain promote adhesion of Helicobacter pylori to the gastric epithelium" -
Molecular Microbiology 35(6) (2000) 1530-1539
Helicobacter pylori NCTC11637 expresses a lipopolysaccharide (LPS) that comprises an O antigen side-chain with structural homology to the human blood group antigen Lewis X (Le(x)). The role of this molecule in adhesion of H. pylori to gastric epithelial cells was investigated. Mutants expressing truncated LPS structures were generated through insertional mutagenesis of rfbM and galE; genes encode GDP mannose pyrophosphorylase and galactose epimerase respectively. Compositional and structural analysis revealed that the galE mutant expressed a rough LPS that lacked an O antigen side-chain. In contrast, an O antigen side-chain was still synthesized by the rfbM mutant, but it lacked fucose and no longer reacted with anti-Le(x) monoclonal antibodies (Mabs). The ability of these mutants to bind to paraffin-embedded sections from the antrum region of a human stomach was assessed. Adhesion of the wild type was characterized by tropic binding to the apical surface of mucosal epithelial cells and cells lining gastric pits. In contrast, both the rfbM and galE mutants failed to demonstrate tropic binding and adhered to the tissue surface in a haphazard manner. These results indicate that LPS and, more specifically, Le(x) structures in the O antigen side-chain play an important role in targeting H. pylori to specific cell lineages within the gastric mucosa. The role of Le(x) in this interaction was confirmed by the tropic binding of synthetic Le(x), conjugated to latex beads, to gastric tissue. The observed pattern of adhesion was indistinguishable from that of wild-type H. pylori
NCBI PubMed ID: 10760152Journal NLM ID: 8712028Publisher: Blackwell Publishing
Correspondence: Nicky.High@man.ac
Institutions: School of Biological Sciences, The University of Manchester, Manchester, UK, Institute for Biological Sciences, National Research Council, Ottawa, ON, Canada, Institute of Pathology, University of Erlangen-Nuremberg, Erlangen, Germany, Department of Microbiology, National University of Ireland Galway, Galway, Ireland
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3. Compound ID: 217
Structure type: homopolymer
Trivial name: glucan, α-D-glucan, dextran, α-1,6-glucan, α-(1,6)-glucan, dextran, α-(1,6)-glucan, α-1,6 dextran, β-1,3-D-glucan
Compound class: EPS, O-polysaccharide, cell wall polysaccharide, glucan, polysaccharide
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158538,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 53
Edwards NJ, Monteiro MA, Walsh EJ, Moran AP, Roberts IS, High NJ "Lewis X structures in the O antigen side-chain promote adhesion of Helicobacter pylori to the gastric epithelium" -
Molecular Microbiology 35(6) (2000) 1530-1539
Helicobacter pylori NCTC11637 expresses a lipopolysaccharide (LPS) that comprises an O antigen side-chain with structural homology to the human blood group antigen Lewis X (Le(x)). The role of this molecule in adhesion of H. pylori to gastric epithelial cells was investigated. Mutants expressing truncated LPS structures were generated through insertional mutagenesis of rfbM and galE; genes encode GDP mannose pyrophosphorylase and galactose epimerase respectively. Compositional and structural analysis revealed that the galE mutant expressed a rough LPS that lacked an O antigen side-chain. In contrast, an O antigen side-chain was still synthesized by the rfbM mutant, but it lacked fucose and no longer reacted with anti-Le(x) monoclonal antibodies (Mabs). The ability of these mutants to bind to paraffin-embedded sections from the antrum region of a human stomach was assessed. Adhesion of the wild type was characterized by tropic binding to the apical surface of mucosal epithelial cells and cells lining gastric pits. In contrast, both the rfbM and galE mutants failed to demonstrate tropic binding and adhered to the tissue surface in a haphazard manner. These results indicate that LPS and, more specifically, Le(x) structures in the O antigen side-chain play an important role in targeting H. pylori to specific cell lineages within the gastric mucosa. The role of Le(x) in this interaction was confirmed by the tropic binding of synthetic Le(x), conjugated to latex beads, to gastric tissue. The observed pattern of adhesion was indistinguishable from that of wild-type H. pylori
NCBI PubMed ID: 10760152Journal NLM ID: 8712028Publisher: Blackwell Publishing
Correspondence: Nicky.High@man.ac
Institutions: School of Biological Sciences, The University of Manchester, Manchester, UK, Institute for Biological Sciences, National Research Council, Ottawa, ON, Canada, Institute of Pathology, University of Erlangen-Nuremberg, Erlangen, Germany, Department of Microbiology, National University of Ireland Galway, Galway, Ireland
- Article ID: 1535
Langdon R, Craig JE, Goldrick M, Houldsworth R, High NJ "Analysis of the role of HP0208, a phase-variable open reading frame, and its homologues HP1416 and HP0159 in the biosynthesis of Helicobacter pylori lipopolysaccharide" -
Journal of Medical Microbiology (2005) 697-706
The roles of the three ORFs HP0208, HP0159 and HP1416 in the biosynthesis of Helicobacter pylori 26695 LPS were investigated in this study. These ORFs represent a paralogous family of genes with homology to the Salmonella enterica serovar Typhimurium (hereafter referred to as S. typhimurium) waaJ gene, which encodes an α-1,2-glycosyltransferase required for core LPS biosynthesis. HP0208 contains multiple tandem repeats of the dimer 5'GA at its 5' end and its expression is predicted to be subject to phase variation. The number of 5'GA repeats present in this ORF was found to be non-permissive for the expression of HP0208 in the majority of H. pylori strains examined. To determine a role for this ORF in LPS biosynthesis a non-phase-variable, constitutively expressed variant of HP0208 was constructed and introduced into the genome of H. pylori 26695. Analysis of the LPS profile of this strain by Tricine-SDS-PAGE and immunoblotting with anti-Lewis Y antigen (Le(y)) mAbs confirmed a role for HP0208 in the biosynthesis of core LPS. A role for HP0159 and HP1416 in the biosynthesis of core LPS was also established. Although homologous to waaJ, H. pylori HP0208, HP0159 and HP1416 failed to complement an S. typhimurium waaJ mutant, suggesting that these ORFs encode functionally different enzymes
Lipopolysaccharide, biosynthesis, antigen, LPS, core, Phase variation, expression, gene, phase, role, strain, variation, analysis, MAb, mutant, Salmonella, families, Salmonella enterica, Helicobacter pylori, enzyme, variant, Enzymes, homology, genome, Helicobacter, Typhimurium, tandem, homologous, complement, multiple, anti-Lewis, immunoblotting, profile
NCBI PubMed ID: 16014421Journal NLM ID: 0224131Publisher: Reading, England: Society for General Microbiology
Institutions: University of Manchester, Faculty of Life Sciences, 1.800 Stopford Building, Oxford Road, Manchester M13 9PT, UK
Methods: genetic methods
- Article ID: 3204
Zdorovenko EL, Varbanets LD, Zatonsky GV, Ostapchuk AN "Structures of two putative O-specific polysaccharides from the Rahnella aquatilis 3-95 lipopolysaccharide" -
Carbohydrate Research 341(1) (2006) 164-168
Two polysaccharide preparations (OPSI and OPSII) were obtained by mild acid degradation of the lipopolysaccharide of Rahnella aquatilis 3-95. Studies by chemical methods and 1H and 13C NMR spectroscopy showed that OPSI has a linear trisaccharide repeat of -d-mannose and OPSII is a mixture of the same mannan and an -(16)-linked d-glucan.
Lipopolysaccharide, O-antigen, bacterial polysaccharide structure, Rahnella aquatilis
NCBI PubMed ID: 16313891Publication DOI: 10.1016/j.carres.2005.11.005Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: evelina@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, D.K. Zabolotny Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, ul. Zabolotnogo 154, 03143 Kiev, Ukraine
Methods: 13C NMR, 1H NMR, methylation, sugar analysis, mild acid hydrolysis
- Article ID: 4328
Knirel YA "Structure of O-antigens" -
Book: Bacterial lipopolysaccharides: Structure, chemical synthesis, biogenesis and interaction with host cells (2011) Chapter 3, 41-115
The lipopolysaccharide (LPS) is the major constituent of the outer leaflet of the outer membrane of Gram-negative bacteria. Its lipid A moiety is embedded in the membrane and serves as an anchor for the rest of the LPS molecule. The outermost repetitive glycan region of the LPS is linked to the lipid A through a core oligosaccharide (OS), and is designated as the O-specific polysaccharide (O-polysaccharide, OPS) or O-antigen. The O-antigen is the most variable portion of the LPS and provides serological specificity, which is used for bacterial serotyping. The OPS also provides protection to the microorganisms from host defenses such as complement mediated killing and phagocytosis, and is involved in interactions of bacteria with plants and bacteriophages. Studies of the OPSs ranging from the elucidation of their chemical structures and conformations to their biological and physico-chemical properties help improving classification schemes of Gram-negative bacteria. Furthermore, these studies contributed to a better understanding of the mechanisms of pathogenesis of infectious diseases, as well as provided information to develop novel vaccines and diagnostic reagents.
Lipopolysaccharide, synthesis, lipopolysaccharides, structure, Bacterial, host, O-antigen, O antigen, cell, O antigens, O-antigens, chemical, interaction, cells, PDF, chemical synthesis, biogenesis
Publication DOI: 10.1007/978-3-7091-0733-1_3Publisher: Springer
Correspondence: knirel@ioc.ac.ru
Editors: Knirel YA, Valvano MA
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
- Article ID: 4549
Kiseleva EP, Mikhailopulo KI, Novik GI, Szwajcer Dey E, Zdorovenko EL, Shashkov AS, Knirel YA "Isolation and structural identification of glycopolymers of Bifidobacterium bifidum BIM B-733D as putative players in pathogenesis of autoimmune thyroid diseases" -
Beneficial Microbes 4(4) (2013) 375-391
Bifidobacterium bifidum 791 (commercially available as B. bifidum BIM B-733D) cell-surface biopolymers (BPs) interact selectively with human serum thyroid peroxidase (TPO) and thyroglobulin (Tg) autoantibodies (anti TPO and anti Tg, respectively). BPanti-TPO and BPanti-Tg were isolated from the soluble fraction of B. bifidum BIM B-733D by affinity chromatography with anti-TPO or anti-Tg, respectively. Homogeneity of affinity eluates (AEanti-TPO and AEanti-Tg) was tested by size exclusion chromatography. For each AE, the elution profiles generated on the basis of absorbance at 280 nm do not conform to ELISA data for functional activity characteristic of BPs. Moreover, high functional activity was detected in chromatographic fractions that had significantly different molecular weights and no absorbance at 280 nm, which suggests a non-protein (carbohydrate) nature of BPanti-TPO and BPanti-Tg. The semi-preparative size exclusion chromatography of AEanti-TPO and AEanti-Tg with detection by refractometer gave 5,000-7,000 Da fractions containing substances that interact selectively with either anti TPO (BPanti-TPO) or anti-Tg (BPanti-Tg) according to ELISA data. Analysis by two-dimensional NMR spectroscopy including a 1H, 13C-heteronuclear single-quantum coherence experiment indicated that both substances are linear α-1,6-glucans. For the first time, an immunological similarity (molecular mimicry) of glycopolymers of B. bifidum BIM B-733D and human thyroid proteins, TPO and Tg, was shown. On the whole, our data point to a possible role of bifidobacteria in the pathogenesis of autoimmune thyroid diseases (ATD). The main requirements for triggering/acceleration or prevention/abrogation of ATD by bifidobacteria through molecular mimicry mechanism are hypothesised to be (1) genetic predisposition to ATD and (2) intestinal epithelium penetration by α-1,6-glucan.
Autoantibodies, molecular mimicry, Bifidobacterium, α-1, 6-glucan
NCBI PubMed ID: 24311320Publication DOI: 10.3920/BM2013.0015Journal NLM ID: 101507616Publisher: Wageningen: Wageningen Academic Publishers
Correspondence: epkiseleva@yandex.ru
Institutions: The Institute of Bioorganic Chemistry, National Academy of Sciences of Belaru, Acad. Kuprevicha 5/2, 220141 Minsk, Republic of Belarus.
Methods: 13C NMR, 1H NMR, NMR-2D, ELISA, serological methods
- Article ID: 4663
Altman E, Chandan V, Harrison B "The potential of dextran-based glycoconjugates for development of Helicobacter pylori vaccine" -
Glycoconjugate Journal 31(1) (2014) 13-24
We have recently demonstrated that synthetic glycoconjugates based on delipidated lipopolysaccharide (LPS) of Helicobacter pylori and containing an α(1-6)-glucan chain induced broadly cross-reactive functional antibodies in immunized animals. To investigate the candidacy of α(1-6)-glucan as an alternative vaccine strategy we prepared glycoconjugates based on dextrans produced by lactic acid bacteria Leuconostoc mesenteroides B512F and consisting of linear α(1-6)-glucan chains with limited branching. Three dextrans with averaged molecular masses of 5,000 Da, 3,500 Da and 1,500 Da, respectively, were modified with a diamino group-containing linker and conjugated to a carrier protein, tetanus toxoid (TT) or diphtheria toxoid (DT), and their immunological properties investigated. The conjugates were immunogenic in both rabbits and mice and induced specific IgG responses against α(1-6)-glucan-expressing H. pylori LPS. Studies performed with post-immune sera of mice and rabbits immunized with dextran-based conjugates demonstrated cross-reactivity with LPS from typeable and non-typeable strains of H. pylori and selected mutants. The post-immune sera from rabbits that received the conjugates exhibited functional activity against α(1-6)-glucan-positive strains of H. pylori. These data provide evidence that dextran-based conjugates may offer a simplified approach to the development of carbohydrate-based vaccines against H. pylori.
Helicobacter pylori, Helicobacter, conjugate vaccine, glycoconjugate, Dextran, Bactericidal assay
NCBI PubMed ID: 23990317Publication DOI: 10.1007/s10719-013-9496-4Journal NLM ID: 8603310Publisher: Kluwer Academic Publishers
Correspondence: Eleonora.altman@nrc-cnrc.gc.ca
Institutions: National Research Council Canada, Ottawa, Ontario, K1A 0R6, Canada
Methods: 1H NMR, methylation, MALDI-TOF MS, biological assays, microscopy, conjugation, MALDI-TOF/TOF MS, bactericidal activity
- Article ID: 4841
Dolfi S, Sveronis A, Silipo A, Rizzo R, Cescutti P "A novel rhamno-mannan exopolysaccharide isolated from biofilms of Burkholderia multivorans C1576" -
Carbohydrate Research 411 (2015) 42-48
Burkholderia multivorans C1576 is a Gram negative opportunistic pathogen causing serious lung infection in cystic fibrosis patients. Considering that bacteria naturally form biofilms, and exopolysaccharides are recognized as important factors for biofilm architecture set-up, B. multivorans was grown both in biofilm and in non-biofilm mode on two different media in order to compare the exopolysaccharides biosynthesized in these different experimental conditions. The exopolysaccharides produced were purified and their structure was determined resorting mainly to NMR spectroscopy, ESI mass spectrometry and gas chromatography coupled to mass spectrometry. The experimental data showed that both in biofilm and non-biofilm mode B. multivorans C1576 produced a novel exopolysaccharide having the following structure: [Formula: see text]. About 50% of the 2-linked rhamnose residues are substituted on C-3 with a methyl ether group. The high percentage of deoxysugar Rha units, coupled with OMe substitutions, suggest a possible role for polymer domains with marked hydrophobic characteristics able to create exopolysaccharide junction zones favouring the stability of the biofilm matrix.
NMR, Exopolysaccharide structure, cystic fibrosis, Biofilm, Burkholderia multivorans C1576
NCBI PubMed ID: 25974852Publication DOI: 10.1016/j.carres.2015.04.012Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: pcescutti@units.it
Institutions: Department of Chemical Sciences, University of Naples 'Federico II', Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, Italy, Department of Life Sciences, Bldg C11, University of Trieste, Via Licio Giorgieri 1, 34127 Trieste, Italy
Methods: 13C NMR, 1H NMR, NMR-2D, partial acid hydrolysis, GC-MS, ESI-MS, GLC, de-O-acetylation, composition analysis, NMR-1D
- Article ID: 4874
Arbatsky NP, Shneider MM, Shashkov AS, Popova AV, Miroshnikov KA, Volozhantsev NV, Knirel YA "Structure of the N-acetylpseudaminic acid-containing capsular polysaccharide of Acinetobacter baumannii NIPH67" -
Russian Chemical Bulletin = Izvestiia Akademii nauk. Seriia khimicheskaia 65(2) (2016) 588-591
Capsular polysaccharide (CPS) was isolated from a nosocomial pathogen Acinetobacter baumannii (A. baumannii) NIPH67 and studied by sugar analysis, Smith degradation, and 1H and 13C NMR spectroscopy. The CPS was found to contain 5,7-diacetamido-3,5,7,9-tetradeoxy-L-glycero-L-manno-non-2-ulosonic acid (di-N-acetylpseudaminic acid, Pse5Ac7Ac), and the structure of the linear trisaccharide repeating unit of the CPS was established as →4)-α-Psep5Ac7Ac-(2→6)-β-D-Galp-(1→3)-α-D-GalpNAc-(1→. The genetic content of the capsule biosynthesis cluster of A. baumannii NIPH67, designated KL33, is consistent with the established CPS structure, and thus the capsule of the investigated strain was assigned to K33 group. Functions of proteins including two glycosyltransferases encoded by the genes of the K33 locus were assigned based on the structure of CPS and by the comparison with related proteins of other capsular types of A. baumannii.
capsular polysaccharide, Acinetobacter baumannii, pseudaminic acid, glycosyltransferase, biotechnology, K locus, KL33 gene cluster, structure of capsular polysaccharide
Publication DOI: 10.1007/s11172-016-1342-yJournal NLM ID: 100912060Publisher: New York: Consultants Bureau
Correspondence: yknirel@gmail.com
Institutions: N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow, Russian Federation, M. M. Shemyakin and Yu. A. Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 ul. MiklukhoMaklaya, 117997 Moscow, Russian Federation, Moscow Institute of Physics and Technology,9 Institutsky per., 141700 Dolgoprudnyi, Moscow Region, Russian Federation, State Research Center for Applied Microbiology and Biotechnology, 142279 Obolensk, Moscow Region, Russian Federation
Methods: 13C NMR, 1H NMR, NMR-2D, acid hydrolysis, GLC, Smith degradation, composition analysis, mild alkaline degradation, GPC, function analysis of gene clusters
- Article ID: 5142
Clarke BR, Ovchinnikova OG, Kelly SD, Williamson ML, Butler JE, Liu B, Wang L, Gou X, Follador R, Lowary TL, Whitfield C "Molecular basis for the structural diversity in serogroup O2-antigen polysaccharides in Klebsiella pneumoniae" -
Journal of Biological Chemistry 293(13) (2018) 4666-4679
Klebsiella pneumoniae is a major health threat. Vaccination and passive immunization are considered as alternative therapeutic strategies for managing Klebsiella infections. Lipopolysaccharide O antigens are attractive candidates because of the relatively small range of known O-antigen polysaccharide structures, but immunotherapeutic applications require a complete understanding of the structures found in clinical settings. Currently, the precise number of Klebsiella O antigens is unknown because available serological tests have limited resolution, and their association with defined chemical structures is sometimes uncertain. Molecular serotyping methods can evaluate clinical prevalence of O serotypes but require a full understanding of the genetic determinants for each O-antigen structure. This is problematic with Klebsiella pneumoniae because genes outside the main rfb (O-antigen biosynthesis) locus can have profound effects on the final structure. Here, we report two new loci encoding enzymes that modify a conserved polysaccharide backbone comprising disaccharide repeat units [→3)-α-d-Galp-(1→3)-β-d-Galf-(1→] (O2a antigen). We identified in serotype O2aeh a three-component system that modifies completed O2a glycan in the periplasm by adding 1,2-linked α-Galp side-group residues. In serotype O2ac, a polysaccharide comprising disaccharide repeat units [→5)-β-d-Galf-(1→3)-β-d-GlcpNAc-(1→] (O2c antigen) is attached to the non-reducing termini of O2a-antigen chains. O2c-polysaccharide synthesis is dependent on a locus encoding three glycosyltransferase enzymes. The authentic O2aeh and O2c antigens were recapitulated in recombinant Escherichia coli hosts to establish the essential gene set for their synthesis. These findings now provide a complete understanding of the molecular genetic basis for the known variations in Klebsiella O-antigen carbohydrate structures based on the O2a backbone.
polysaccharide, O antigen, polysaccharide structure, Gram-negative bacteria, glycosyltransferase, serotyping, lipopolysaccharide (LPS), carbohydrate structure, nuclear magnetic resonance (NMR), Klebsiella pneumonia
NCBI PubMed ID: 29602878Publication DOI: 10.1074/jbc.RA117.000646Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: cwhitfie@uoguelph.ca
Institutions: TEDA Institute of Biological Sciences and Biotechnology, Nankai University, 23 Hongda St. TEDA, Tianjin, China, LimmaTech Biologics AG, 8952 Schlieren, Switzerland, and the Department of Chemistry and Alberta Glycomics Centre, University of Alberta, Edmonton, AB, Canada, the Department of Molecular and Cellular Biology, University of Guelph, Guelph, Ontario, Canada N1G 2W1
Methods: gel filtration, 13C NMR, 1H NMR, NMR-2D, PCR, DNA sequencing, SDS-PAGE, DNA techniques, bioinformatic analysis, mmunoblotting
- Article ID: 5267
Agarwal S, Specht CA, Haibin H, Ostroff GR, Ram S, Rice PA, Levitz SM "Linkage specificity and role of properdin in activation of the alternative complement pathway by fungal glycans" -
mBio 2(5) (2011) 1-10
Fungal cell walls are predominantly composed of glucans, mannans, and chitin. Recognition of these glycans by the innate immune system is a critical component of host defenses against the mycoses. Complement, an important arm of innate immunity, plays a significant role in fungal pathogenesis, especially the alternative pathway (AP). Here we determine that the glycan monosaccharide composition and glycosidic linkages affect AP activation and C3 deposition. Furthermore, properdin, a positive regulator of the AP, contributes to these functions. AP activation by glycan particles that varied in composition and linkage was measured by C3a generation in serum treated with 10 mM EGTA and 10 mM Mg(2+) (Mg-EGTA-treated serum) (AP specific; properdin functional) or Mg-EGTA-treated serum that lacked functional properdin. Particles that contained either β1→3 or β1→6 glucans or both generated large and similar amounts of C3a when the AP was intact. Blocking properdin function resulted in 5- to 10-fold-less C3a production by particulate β1→3 glucans. However, particulate β1→6 glucans generated C3a via the AP only in the presence of intact properdin. Interestingly, zymosan and glucan-mannan particles (GMP), which contain both β-glucans and mannans, also required properdin to generate C3a. The β1→4 glycans chitin and chitosan minimally activated C3 even when properdin was functional. Finally, properdin binding to glucan particles (GP) and zymosan in serum required active C3. Properdin colocalized with bound C3, suggesting that in the presence of serum, properdin bound indirectly to glycans through C3 convertases. These findings provide a better understanding of how properdin facilitates AP activation by fungi through interaction with the cell wall components.
properdin
NCBI PubMed ID: 21878570Publication DOI: 10.1128/mBio.00178-11Journal NLM ID: 101519231Publisher: Washington, DC: American Society for Microbiology
Correspondence: sarika.agarwal@umassmed.edu
Institutions: Department of Medicine, University of Massachusetts Medical School, Worcester, Massachusetts, USA, Program in Molecular Medicine, University of Massachusetts Medical School, Worcester, Massachusetts, USA
Methods: enzyme immunoassay, electrophoresis, extraction, confocal microscopy, flow cytometry
- Article ID: 5283
Chi Z, Su CD, Lu WD "A new exopolysaccharide produced by marine Cyanothece sp. 113" -
Bioresource Technology 98(6) (2007) 1329-1332
Cyanothece sp. 113, a unicellular, aerobic, diazotrophic and photosynthetic marine cyanobacterium, produced 22.34 g/l of exopolysaccharide in 11 days at 29 °C, aeration rate of 7.0 l/min and continuous illumination with 4300 lux. After purification, the spectra of UV, IR, 1H NMR, 13C NMR and GC-MS analysis showed that the purified exopolysaccharide was α-D-1,6-homoglucan. This is first report describing linear α-D-1,6-homoglucan exopolysaccharide produced by marine cyanobacteria.
exopolysaccharide, glucan, aeration rate, Cyanothece, marine cyanobacteria
NCBI PubMed ID: 16782333Publication DOI: 10.1016/j.biortech.2006.05.001Journal NLM ID: 9889523Publisher: Elsevier
Correspondence: zhenming@sdu.edu.cn
Institutions: UNESCO Chinese Center of Marine Biotechnology, Ocean University of China, Qingdao, China
Methods: 13C NMR, 1H NMR, GC-MS, acid hydrolysis, FTIR, GPC, UV, extraction, cell growth, ethanol precipitation
- Article ID: 5333
Palomba S, Cavella S, Torrieri E, Piccolo A, Mazzei P, Blaiotta G, Ventorino V, Pepe O "Polyphasic screening, homopolysaccharide composition, and viscoelastic behavior of wheat Sourdough from a Leuconostoc lactis and Lactobacillus curvatus exopolysaccharide-producing starter culture" -
Applied and Environmental Microbiology 78(8) (2012) 2737-2747
After isolation from different doughs and sourdoughs, 177 strains of lactic acid bacteria were screened at the phenotypic level for exopolysaccharide production on media containing different carbohydrate sources. Two exopolysaccharide-producing lactic acid bacteria (Lactobacillus curvatus 69B2 and Leuconostoc lactis 95A) were selected through quantitative analysis on solid media containing sucrose and yeast extract. The PCR detection of homopolysaccharide (gtf and lev) and heteropolysaccharide (epsA, epsB, epsD and epsE, and epsEFG) genes showed different distributions within species and strains of the lactic acid bacteria studied. Moreover, in some strains both homopolysaccharide and heteropolysaccharide genes were detected. Proton nuclear magnetic resonance spectra suggest that Lactobacillus curvatus 69B2 and Leuconostoc lactis 95A produced the same exopolysaccharide, which was constituted by a single repeating glucopyranosyl unit linked by an α-(1→6) glycosidic bond in a dextran-type carbohydrate. Microbial growth, acidification, and viscoelastic properties of sourdoughs obtained by exopolysaccharide-producing and nonproducing lactic acid bacterial strains were evaluated. Sourdough obtained after 15 h at 30°C with exopolysaccharide-producing lactic acid bacteria reached higher total titratable acidity as well as elastic and dissipative modulus curves with respect to the starter not producing exopolysaccharide, but they showed similar levels of pH and microbial growth. On increasing the fermentation time, no difference in the viscoelastic properties of exopolysaccharide-producing and nonproducing samples was observed. This study suggests that dextran-producing Leuconostoc lactis 95A and Lactobacillus curvatus 69B2 can be employed to prepare sourdough, and this would be particularly useful to improve the quality of baked goods while avoiding the use of commercially available hydrocolloids as texturizing additives.
exopolysaccharide, Dextran, α-D-glucan, Leuconostoc lactis, Lactobacillus curvatus
NCBI PubMed ID: 22307283Publication DOI: 10.1128/AEM.07302-11Journal NLM ID: 7605801Publisher: American Society for Microbiology
Correspondence: olipepe@unina.it
Institutions: Dipartimento di Scienza degli Alimenti, Università degli Studi di Napoli Federico II, Portici, Italy, Centro Interdipartimentale di Ricerca Sulla Risonanza Magnetica Nucleare (CERMANU), Università Degli Studi di Napoli Federico II, Portici, Italy
Methods: 13C NMR, 1H NMR, NMR-2D, DNA techniques, extraction, rheological study
- Article ID: 5632
Lee G, Nowak W, Jaroniec J, Zhang Q, Marszalek PE "Molecular dynamics simulations of forced conformational transitions in 1,6-linked polysaccharides" -
Biophysical Journal 87(3) (2004) 1456-1465
Recent atomic force microscopy stretching measurements of single polysaccharide molecules suggest that their elasticity is governed by force-induced conformational transitions of the pyranose ring. However, the mechanism of these transitions and the mechanics of the pyranose ring are not fully understood. Here we use steered molecular dynamics simulations of the stretching process to unravel the mechanism of forced conformational transitions in 1,6 linked polysaccharides. In contrast to most sugars, 1,6 linked polysaccharides have an extra bond in their inter-residue linkage, C5-C6, around which restricted rotations occur and this additional degree of freedom increases the mechanical complexity of these polymers. By comparing the computational results with the atomic force microscopy data we determine that forced rotations around the C5-C6 bond have a significant and different impact on the elasticity of α- and β-linked polysaccharides. β-linkages of a polysaccharide pustulan force the rotation around the C5-C6 bonds and produce a Hookean-like elasticity but do not affect the conformation of the pyranose rings. However, α-linkages of dextran induce compound conformational transitions that include simultaneous rotations around the C5-C6 bonds and chair-boat transitions of the pyranose rings. These previously not-recognized transitions are responsible for the characteristic plateau in the force-extension relationship of dextran
molecular dynamics, Glucans, atomic force microscopy, Dextran
NCBI PubMed ID: 15345528Publication DOI: 10.1529/biophysj.104.042879Journal NLM ID: 0370626Publisher: Cambridge, MA: Cell Press
Correspondence: Marszalek PE
Institutions: Department of Mechanical Engineering and Materials Science, Duke University, Durham, USA, Center for Bioinspired Materials and Material Systems, Duke University, Durham, USA, Institute of Physics, Nicholaus Copernicus University, Toruń, Poland
Methods: molecular modeling, AFM
- Article ID: 6270
Lobo RE, Orrillo PA, Ribotta SB, de Valdez GF, García MS, Cabello JCR, Torino MI "Structural characterization of a homopolysaccharide produced by Weissella cibaria FMy 2-21-1 and its potential application as a green corrosion inhibiting film" -
International Journal of Biological Macromolecules 212 (2022) 193-201
Steel corrosion is a global issue that affects safety and the economy. Currently, the homopolysaccharide (HoPS) structure of a novel lactic acid bacterium (LAB) is under study, as well as its application as a green corrosion inhibitor. Weissella cibaria FMy 2-21-1 is a LAB strain capable of producing HoPS in sucrose enriched media. The isolated and purified HoPS was characterized by different spectroscopic analyses as a linear α-1,6 dextran adopting a random coil conformation, with high molecular weight and extended size in water. The polysaccharide showed a semi-crystalline organization, which is a requirement for film formation. Its biocoating showed a grainy network structure, with a slightly lesser hydrophobic role in the aqueous environment than in the ionic one. The electrochemical measurements of the steel-HoPS coating showed that the biopolymer layer acts as an anodic-type corrosion inhibitor, with high resistance to corrosion by water and with chloride ions which prevent pitting, a corrosion process typical of bare steel. Few reports have cited the application of LAB HoPS as corrosive coating inhibitors. This work is the first to explore the influence of a structurally characterized dextran from Weissella cibaria strain as a potential steel corrosion inhibitor in ionic environments.
Lactic acid bacteria, LAB, biocoating, corrosion inhibitor, HoPS structure, Weissella cibaria
NCBI PubMed ID: 35594939Publication DOI: 10.1016/j.ijbiomac.2022.05.105Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: mitorino@cerela.org.ar
Institutions: Centro de Referencia para Lactobacilos (CERELA)-CCT CONICET NOA Sur, Batalla de Chacabuco 145, San Miguel de Tucumán 4000, Tucumán, Argentina, Instituto de Química del Noroeste Argentino (INQUINOA) - Universidad Nacional de Tucumán (UNT) - CCT CONICET NOA Sur, Instituto de Química Física, Facultad de Bioquímica, Química y Farmacia, UNT, Batalla de Ayacucho 471, San Miguel de Tucumán 4000, Tucumán, Argentina, BIOFORGE (Group for Advanced Materials and Nanobiotechnology), University of Valladolid, CIBER-BBN, Valladolid, Spain
Methods: 13C NMR, 1H NMR, NMR-2D, UV, CD, statistical analysis, AFM, XRD, DLS, SLS, Congo red test, FT-R, SERS, electrochemical measurements
- Article ID: 6786
Youssef F, Roukas T, Biliaderis CG "Pullulan production by a non-pigmented strain of Aureobasidium pullulans using batch and fed-batch culture" -
Process Biochemistry 34 (1999) 355-366
The production of pigment-free pullulan by Aureobasidium pullulans in batch and fed-batch culture was investigated. Batch culture proved to be a better fermentation system for the production of pullulan than the fed-batch culture system. A maximum polysaccharide concentration (31.3 g l−1), polysaccharide productivity (4.5 g l−1 per day), and sugar utilization (100%) were obtained in batch culture. In fed-batch culture, feed medium composition influenced the kinetics of fermentation. For fed-batch culture, the highest values of pullulan concentration (24.5 g l−1) and pullulan productivity (3.5 g l−1 per day) were obtained in culture grown with feeding substrate containing 50 g l−1 sucrose and all nutrients. The molecular size of pullulan showed a decline as fermentation progressed for both fermentation systems. At the end of fermentation, the polysaccharide isolated from the fed-batch culture had a slightly higher molecular weight than that of batch culture. Structural characterization of pullulan samples (methylation and enzymic hydrolysis with pullulanase) revealed the presence of mainly α-(1→4) (~66%) and α-(1→6) (~31%) glucosidic linkages; however, a small amount (<3%) of triply linked (1,3,4-, 1,3,6-, 1,2,4- and 1,4,6-Glc p) residues were detected. The molecular homogeneity of the alcohol-precipitated polysaccharides from the fermentation broths as well as the structural features of pullulan were confirmed by 13C-NMR and pullulanase treatments followed by gel filtration chromatography of the debranched digests.
pullulan, Aureobasidium pullulans, batch culture, fed-batch culture
Publication DOI: 10.1016/S0032-9592(98)00106-XJournal NLM ID: 9211419Publisher: Barking, Essex: Elsevier Applied Science
Correspondence: roukas@agro.auth.gr
Institutions: Mediterranean Agronomic Institute of Chania, Alsyllion Agrokepion, PO Box 85, Chania, Crete GR-73 100, Greece, Department of Food Science and Technology, Aristotle University of Thessaloniki, Box 250, 540 06 Thessaloniki, Greece
Methods: gel filtration, 13C NMR, GC-MS, GC, enzymatic digestion, methylation analysis
- Article ID: 6848
Rout D, Mondal S, Chakraborty I, Pramanik M, Islam SS "Structural characterisation of an immunomodulating polysaccharide isolated from aqueous extract of Pleurotus florida fruit-bodies" -
Medicinal Chemistry Research 13(6-7) (2004) 509-517
The water-soluble glucan was obtained from Pleurotus florida fruit bodies by hot water extraction, ethanol precipitation, DEAE cellulose dialysis and Sephadex G-75 gel filtration. The structural information of the glucan was achieved by chemical (hydrolysis, methylation, periodate oxidation) and spectroscopic (H-1 and C-13) analyses, indicated a repeating unit built up of (1 -> 6)-linked D-glucose. The following structure has been determined for the repeating unit: -> 6)-alpha-D-Glc(p)-(1 -> This fraction exhibited significant macrophage activity through the release of nitric oxide.
glucan, fungi, branched (1-3)-beta-D-glucan, antitumor polysaccharides, alkaline extract, chinese mushroom
Publication DOI: 10.1007/s00044-004-0050-6Journal NLM ID: 9211347Publisher: Cambridge, MA: Birkhäuser Boston; New York: Springer
Correspondence: sirajul_1999@yahoo.com
Institutions: Department of Chemistry & Chemical Technology, Vidyasagar University, Midnapore, West Bengal, 721 102, India
Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GLC-MS, sugar analysis, acid hydrolysis, GLC, periodate oxidation
- Article ID: 7855
Elsayed EA, El Enshasy H, Wadaan MA, Aziz R "Mushrooms: a potential natural source of anti-inflammatory compounds for medical applications" -
Mediators of Inflammation 2014 (2014) ID 805841
For centuries, macrofungi have been used as food and medicine in different parts of the world. This is mainly attributed to their nutritional value as a potential source of carbohydrates, proteins, amino acids, and minerals. In addition, they also include many bioactive metabolites which make mushrooms and truffles common components in folk medicine, especially in Africa, the Middle East, China, and Japan. The reported medicinal effects of mushrooms include anti-inflammatory effects, with anti-inflammatory compounds of mushrooms comprising a highly diversified group in terms of their chemical structure. They include polysaccharides, terpenoids, phenolic compounds, and many other low molecular weight molecules. The aims of this review are to report the different types of bioactive metabolites and their relevant producers, as well as the different mechanisms of action of mushroom compounds as potent anti-inflammatory agents.
reishi, Ganoderma, ganoderic acid
NCBI PubMed ID: 25505823Publication DOI: 10.1155/2014/805841Journal NLM ID: 9209001Publisher: Sylvania, OH: Hindawi Pub. Corp.
Correspondence: Elsayed EA
Institutions: Bioproducts Research Chair, Zoology Department, Faculty of Science, King Saud University, Riyadh, Saudi Arabia, Natural and Microbial Products Department, National Research Centre, Cairo, Egypt, Institute of Bioproduct Development, Universiti Teknologi Malaysia, Skudai, Malaysia, City of Scientific Research and Technology Application, New Burg Al Arab, Alexandria, Egypt
- Article ID: 7894
Synytsya A, Novák M "Structural diversity of fungal glucans" -
Carbohydrate Polymers 92(1) (2013) 729-809
Fungal glucans represent various structurally different d-glucose polymers with a large diversity of molecular mass and configuration. According to glucose anomeric structure, it is possible to distinguish α-D-glucans, β-D-glucans and mixed α,β-D-glucans. Further discrimination could be made on the basis of glycosidic bond position in a pyranoid ring, distribution of specific glycosidic bonds along a chain, branching and molecular mass. Fungal glucans can be chemically modified to obtain various derivatives of potential industrial or medicinal importance. NMR spectroscopy is a powerful tool in structural analysis of fungal glucans. Together with chemolytic methods like methylation analysis and periodate oxidation, NMR is able to determine exact structure of these polysaccharides. Fungal glucans or their derivatives exert various biological activities, which are usually linked to structure, molecular mass and substitution degree.
nuclear magnetic resonance, chemical modification, fungal glucans, structural diversity, structure–activity relationship
NCBI PubMed ID: 23218369Publication DOI: 10.1007/s11101-013-9301-9Journal NLM ID: 8307156Publisher: Elsevier
Correspondence: Synytsya A
Institutions: Department of Carbohydrates and Cereals, Institute of Chemical Technology in Prague, Prague, Czech Republic
Methods: 13C NMR, 1H NMR, enzymatic hydrolysis, extraction, ROESY, methylation analysis, HMBC, SEM, HMQC, NOESY, HSQC, immunocytochemical analyses, HSBC
- Article ID: 8226
Kagimura FY, da Cunha MAA, Barbosa AM, Dekker RFH, Malfatti CRM "Biological activities of derivatized D-glucans: A review" -
International Journal of Biological Macromolecules 72 (2015) 588-598
D-Glucans have triggered increasing interest in commercial applications in the chemical and pharmaceutical sectors because of their technological properties and biological activities. The glucans are foremost among the polysaccharide groups produced by microorganisms with demonstrated activity in stimulating the immune system, and have potential in treating human disease conditions. Chemical alterations in the structure of D-glucans through derivatization (sulfonylation, carboxymethylation, phosphorylation, acetylation) contributes to their increased solubility that, in turn, can alter their biological activities such as antioxidation and anticoagulation. This review surveys and cites the latest advances on the biological and technological potential of D-glucans following chemical modifications through sulfonylation, carboxymethylation, phosphorylation or acetylation, and discusses the findings of their activities. Several studies suggest that chemically modified D-glucans have potentiated biological activity as anticoagulants, antitumors, antioxidants, and antivirals. This review shows that indepth future studies on chemically modified glucans with amplified biological effects will be relevant in the biotechnological field because of their potential to prevent and treat numerous human disease conditions and their clinical complications
exopolysaccharides, α- and β-Glucans, biomolecules
NCBI PubMed ID: 25239192Publication DOI: 10.1016/j.ijbiomac.2014.09.008Journal NLM ID: 7909578Publisher: Butterworth-Heinemann
Correspondence: mcunha@utfpr.edu.br
Institutions: Departamento de Química, Universidade Tecnológica Federal do Paraná, Pato Branco, Brazil, Departamento de Química - CCE, Universidade Estadual de Londrina, Londrina, Brazil, Biorefining and Biotechnology Consultancy, Londrina, Brazil, Universidade Estadual do Centro-Oeste (Programa de Pós-Graduac¸ ão em Ciências Farmacêuticas), Campus CEDETEG, Guarapuava, Brazil
- Article ID: 12089
Kačuráková M, Capek P, Sasinková V, Wellner N, Ebringerova A "FT-IR study of plant cell wall model compounds: pectic polysaccharides and hemicelluloses" -
Carbohydrate Polymers 43(2) (2000) 195-203
Pectic polysaccharides and hemicelluloses extracted from plants were studied in highly hydrated films on BaF2 discs. Distinctive absorption band maxima in the mid-infrared region at 1200–800 1/cm were shown to be useful for the identification of polysaccharides with different structure and composition. Two series of the hexopyranose and pentopyranose monosaccharides, which are the structural units of the plant cell wall polysaccharides, were also studied by FT-IR spectroscopy in solution (i.e. comparable to the amorphous state of the polymers). Their spectral data showed that the main IR band positions are influenced by the relative position of axial and equatorial (OH) groups on the pyranoid ring.
polysaccharides, cell wall, monosaccharides, FT-IR spectroscopy
Publication DOI: 10.1016/S0144-8617(00)00151-XJournal NLM ID: 8307156Publisher: Elsevier
Institutions: Institute of Chemistry, Slovak Academy of Sciences, Bratislava, Slovakia, Institute of Food Research, Norwich Research Park, Colney, UK
Methods: 13C NMR, 1H NMR, methylation, IR, acid hydrolysis, acetylation, methylation analysis
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4. Compound ID: 800
|
a-D-Glcp-(1-6)-+
|
-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-4)-a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1- |
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Structure type: polymer chemical repeating unit
; 65000-87000
Trivial name: glycan PS1A1
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158538,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 210
Wang R, Klegerman ME, Marsden I, Sinnott M, Groves MJ "An anti-neoplastic glycan isolated from Mycobacterium bovis (BCG vaccine)" -
Biochemical Journal 311 (1995) 867-872
Tice substrain BCG is used clinically as an immunotherapeutic agent against superficial bladder cancer. A bioling-water extract of this BCG showed anti-tumour activity against a muringe S180 sarcoma model and was fractionated into three fractions, A, B and C, by the use of Sephades LH-20 chromatography. An antitumour glucan, PS1A1, was isolated from fraction PS1A with Sephadex G-75. The molecular mass of PS1A1 was between 65 and 87 kDa by Sephadex G-100 chromatography. The structure of PS1A1 was investigated by one- and two-dimensional NMR spectroscopy and methylation analysis and was demonstrated to by primarily 1→6-a-linked glucose units. We postulate that the repeating unit is: [see formula in text]
NMR, structure, glycan, Mycobacterium, Mycobacteria, immunotherapeutic, BCG vaccine
NCBI PubMed ID: 7487943Journal NLM ID: 2984726RPublisher: London, UK : Published by Portland Press on behalf of the Biochemical Society
Institutions: Institute fro Tuberculosis Research (College of Pharmace), Universit of Illinois at Chicago (M/C 964), 950 South Halsted Street, Room 2014 SEL, Chicago, IL 60607-7019, Department of Chemistry (College of Liberal Arts and Sciences), Universtiy of Illinois at Chicago (M/C 111), 845 West Taylor Street, Room 4176 SES, Chicago, IL 60607-7061, USA
Methods: NMR-2D, methylation, NMR
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5. Compound ID: 917
|
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
|
Subst-(1-7)-+ | P-7)-+
| | |
a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-2)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
Subst = O-antigen |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_136044,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158538,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 261
Holst O "On the occurrence of D-glycero-D-manno-heptose in lipopolysaccharides" -
Polish Journal of Chemistry 73 (1999) 1055-1067
Lipopolysaccharides (LPS) consist of three regions, i.e. the lipid A, the core region, and the O-specific polysaccharide. The core region and the lipid A represent a common structural unit occurring in all LPS. The structures of the core region of various bacteria have been investigated intensively for the past ten years, and several core regions containing D-glycero-D-manno-heptose which is the biosynthetic precursor of the common core constituent L-glycero-D-manno-heptose have been identified. In this review, these core structures are summarized and briefly discussed.
Lipopolysaccharide, lipopolysaccharides, core, D-glycero-D-manno-heptose, composition, occurrence
Journal NLM ID: 7901356WWW link: http://www.ichf.edu.pl/pjch/pj-1999/pj0799.htm#1055Publisher: Państwowe Wydawnictwo Naukowe
Institutions: Research Center Borstel, Center for Medicine and Biosciences, 23845 Borstel, Germany
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6. Compound ID: 918
|
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
|
a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-2)-+ | P-7)-+
| | |
D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-6)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/ |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_136044,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158538,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 261
Holst O "On the occurrence of D-glycero-D-manno-heptose in lipopolysaccharides" -
Polish Journal of Chemistry 73 (1999) 1055-1067
Lipopolysaccharides (LPS) consist of three regions, i.e. the lipid A, the core region, and the O-specific polysaccharide. The core region and the lipid A represent a common structural unit occurring in all LPS. The structures of the core region of various bacteria have been investigated intensively for the past ten years, and several core regions containing D-glycero-D-manno-heptose which is the biosynthetic precursor of the common core constituent L-glycero-D-manno-heptose have been identified. In this review, these core structures are summarized and briefly discussed.
Lipopolysaccharide, lipopolysaccharides, core, D-glycero-D-manno-heptose, composition, occurrence
Journal NLM ID: 7901356WWW link: http://www.ichf.edu.pl/pjch/pj-1999/pj0799.htm#1055Publisher: Państwowe Wydawnictwo Naukowe
Institutions: Research Center Borstel, Center for Medicine and Biosciences, 23845 Borstel, Germany
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7. Compound ID: 919
|
a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
|
a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-2)-+ | P-7)-+
| | |
Subst-(1-3)-b-D-Galp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-6)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdop-(2--/lipid A/
Subst = Lewis (y) antigen |
Show graphically |
Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_136044,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158538,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 261
Holst O "On the occurrence of D-glycero-D-manno-heptose in lipopolysaccharides" -
Polish Journal of Chemistry 73 (1999) 1055-1067
Lipopolysaccharides (LPS) consist of three regions, i.e. the lipid A, the core region, and the O-specific polysaccharide. The core region and the lipid A represent a common structural unit occurring in all LPS. The structures of the core region of various bacteria have been investigated intensively for the past ten years, and several core regions containing D-glycero-D-manno-heptose which is the biosynthetic precursor of the common core constituent L-glycero-D-manno-heptose have been identified. In this review, these core structures are summarized and briefly discussed.
Lipopolysaccharide, lipopolysaccharides, core, D-glycero-D-manno-heptose, composition, occurrence
Journal NLM ID: 7901356WWW link: http://www.ichf.edu.pl/pjch/pj-1999/pj0799.htm#1055Publisher: Państwowe Wydawnictwo Naukowe
Institutions: Research Center Borstel, Center for Medicine and Biosciences, 23845 Borstel, Germany
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8. Compound ID: 1023
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a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
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Subst-(1-7)-+ | P-7)-+
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{{{-a-D-Glcp-(1-6)-}}}a-D-Glcp-(1-2)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-a-Kdo-(2--/lipid A/
Subst = O-antigen (ID 333) |
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Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_136044,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158538,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 310
Logan SM, Conlan JW, Monteiro MA, Wakarchuk WW, Altman E "Functional genomics of Helicobacter pylori: identification of a b-1,4 galactosyltransferase and generation of mutants with altered lipopolysaccharide" -
Molecular Microbiology 35(5) (2000) 1156-1167
A previously annotated open reading frame (ORF) (HP0826) from Helicobacter pylori was cloned and expressed in Escherichia coli cells and determined to be a β-1,4-galactosyltransferase that used GlcNAc as an acceptor. Mutational analysis in H. pylori strains demonstrated that this enzyme plays a key role in the biosynthesis of the type 2 N-acetyl-lactosamine (LacNAc) polysaccharide O-chain backbone, by catalysing the addition of Gal to GlcNAc. To examine the potential role of this O-chain structure in bacterial colonization of the host stomach, the mutation was introduced into H. pylori strain SS1 which is known to be capable of colonizing the gastric mucosa of mice. Compared with the parental strain, mutated SS1 was less efficient at colonizing the murine stomach.
Lipopolysaccharide, mutants, Helicobacter pylori, galactosyltransferase, Helicobacter, genomics
NCBI PubMed ID: 10712696Publication DOI: 10.1046/j.1365-2958.2000.01784.xJournal NLM ID: 8712028Publisher: Blackwell Publishing
Correspondence: susan.logan@nrc.ca
Institutions: Institute for Biological Sciences, National Research Council of Canada, Ottawa, Ontario, Canada, K1A OR6.
Methods: methylation, FAB-MS
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9. Compound ID: 1449
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a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
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Subst-(1-7)-+ | EtN-(1--P--7)--+
| | |
{{{-a-D-Glcp-(1-6)-}}}a-D-Glcp-(1-2)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
Subst = O-side chain antigen (ID 332) |
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Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_120354,IEDB_123890,IEDB_130650,IEDB_136044,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158538,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 461
Moran AP, Shiberu B, Ferris JA, Knirel YA, Senchenkova SN, Perepelov AV, Jansson P, Goldberg JB "Role of Helicobacter pylori rfaJ genes (HP0159 and HP1416) in lipopolysaccharide synthesis" -
FEMS Microbiology Letters 241(1) (2004) 57-65
The genome of Helicobacter pylori 26695 has been sequenced and the lipopolysaccharide (LPS) O sidechain of this strain has been shown to express both Lewis x and Lewis y units. To determine the role of HP0159 and HP1416, genes recognized as rfaJ homologs and implicated in LPS synthesis, isogenic mutants of H. pylori 26695 were generated. The LPS of mutant 26695::HP0159Kan did not express either Lewis epitope as detected by immunoblotting, whereas the control strain and 26695::HP1416Kan produced both epitopes. Structural analysis of the LPS of the mutants showed that HP0159 encodes an α(1,2/3)-glucosyltransferase whereas HP1416 encodes an α(1,2/4)-glucosyltransferase.
Lipopolysaccharide, core oligosaccharide, Helicobacter pylori, glycosyltransferase, Lewis antigen
NCBI PubMed ID: 15556710Publication DOI: 10.1016/j.femsle.2004.10.004Journal NLM ID: 7705721Publisher: Blackwell Publishing
Correspondence: jbg2b@virginia.edu
Institutions: Department of Microbiology, National University of Ireland, Galway, Ireland
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10. Compound ID: 1474
Structure type: oligomer
Aglycon: protein
Compound class: S-layer glycoprotein
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_150900,IEDB_158538,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 467
Schäffer C, Messner P "Surface-layer glycoproteins: an example for the diversity of bacterial glycosylation with promising impacts on nanobiotechnology" -
Glycobiology 14(8) (2004) 31R-42R
Bacterial cell surface layers, referred to simply as S-layers, have been described for all major phylogenetic groups of bacteria, which may indicate their pivotal role for a bacterium in its natural habitat. They have the unique ability to assemble into two-dimensional crystalline arrays that completely cover the bacterial cells. Glycosylation represents the most frequent modification of S-layer proteins. S-layer glycoproteins constitute a class of glycoconjugates first isolated in the mid-1970s, but S-layer glycoprotein research is still being regarded as an 'exotic field of glycobiology,' possibly because of its 'noneukaryotic' character. Extensive work over the past 30 years provided evidence of an enormous diversity of S-layer glycoproteins that have been created in nature over 3 billion years of prokaryotic evolution. These glycoconjugates are substantially different from eukaryotic glycoproteins, with regard to both composition and structure; nevertheless, some general structural concepts may be deduced. The awareness of the high application potential of S-layer glycoproteins, especially in combination with their intrinsic cell surface display feature, in the field of modern nanobiotechnology as a base for glycoengineering has recently led to the investigation of the S-layer protein glycosylation process at the molecular level, which has lagged behind the structural studies due to the lack of suitable molecular tools. From that work an even more interesting picture of this class of glycoconjugates is emerging. The availability of purified enzymes from S-layer glycan biosynthesis pathways exhibiting increased stabilities and/or rare sugar specificities in conjunction with preliminary genomic data on S-layer glycan biosynthesis clusters will pave the way for the rational design of S-layer neoglycoproteins.
LPS, bacterial glycosylation, genomic glycosylation loci, glycan diversity, glycoengineering, S-layer nanoglycobiology
NCBI PubMed ID: 15044388Publication DOI: 10.1093/glycob/cwh064Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: paul.messner@boka.ac.at
Institutions: Center for NanoBiotechnology, University of Applied Life Sciences and Natural Resources, Gregor-Mendel-Strasse 33, A-1180 Wien, Austria
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11. Compound ID: 1810
Structure type: polymer chemical repeating unit
Trivial name: glucan
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158538,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 568
Dinadayala P, Lemassu A, Granovski P, Cérantola S, Winter N, Daffé M "Revisiting the structure of the anti-neoplastic glucans of Mycobacterium bovis Bacille Calmette-Guérin. Structural analysis of the extracellular and boiling water extract-derived glucans of the vaccine substrains" -
Journal of Biological Chemistry 279(13) (2004) 12369-78
The attenuated strain of Mycobacterium bovis, Bacille Calmette-Guérin (BCG), used worldwide to prevent tuberculosis and leprosy is also clinically used as an immunotherapeutic agent against superficial bladder cancer. An anti-tumor polysaccharide has been isolated from the boiling-water extract of the Tice substrain of BCG and tentatively characterized as consisting primarily of repeating units of 6-linked-glucosyl residues. M. tuberculosis and other mycobacterial species produce a glycogen-like α-glucan, composed of repeating units of 4-linked-glucosyl residues substituted at some positions 6 by short oligoglucosyl units, that also exhibits an anti-tumor activity. Therefore, the impression prevails that mycobacteria synthesize different types of anti-neoplastic glucans or, alternatively, the BCG substrains are singular in producing a unique type of glucan that may confer to them their immunotherapeutic property. The present study addresses this question through the comparative analysis of α-glucans purified from the extracellular materials and boiling-water extracts of three vaccine substrains. The polysaccharides were purified and their structural features were established by mono-and two-dimensional NMR spectroscopy and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of the enzymatic and chemical degradation products of the purified compounds. The glucans isolated by the two methods from the three substrains of BCG were shown to exhibit identical structural features shared with the glycogen-like α-glucan of M. tuberculosis and other mycobacteria. Incidentally, we observed an occasional release of dextrans from Sephadex columns that may explain the reported occurrence of 6-substituted-α-glucans in mycobacteria.
structure, NMR spectroscopy, Mycobacterium, vaccine, glucan, tuberculosis
NCBI PubMed ID: 14715664Publication DOI: 10.1074/jbc.M308908200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: mamadou.daffe@ipbs.fr
Institutions: Departement Mecanismes Moleculaires des Infections Mycobacteriennes, Institut de Pharmacologie et Biologie Structurale, UMR 5089 du CNRS et de l'Universite Paul Sabatier, 205 route de Narbonne, 31077 Toulouse cedex 04, France
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, GC, RT-PCR, aminopyrene trisulfonic acid derivatization
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12. Compound ID: 1812
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a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-+
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-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1-4)-a-D-Glcp-(1- |
Show graphically |
Structure type: polymer chemical repeating unit
Trivial name: repeating unit types of the glycogen-like glucan
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158538,IEDB_420417,IEDB_420418,IEDB_420419,IEDB_420421,IEDB_857742,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 568
Dinadayala P, Lemassu A, Granovski P, Cérantola S, Winter N, Daffé M "Revisiting the structure of the anti-neoplastic glucans of Mycobacterium bovis Bacille Calmette-Guérin. Structural analysis of the extracellular and boiling water extract-derived glucans of the vaccine substrains" -
Journal of Biological Chemistry 279(13) (2004) 12369-78
The attenuated strain of Mycobacterium bovis, Bacille Calmette-Guérin (BCG), used worldwide to prevent tuberculosis and leprosy is also clinically used as an immunotherapeutic agent against superficial bladder cancer. An anti-tumor polysaccharide has been isolated from the boiling-water extract of the Tice substrain of BCG and tentatively characterized as consisting primarily of repeating units of 6-linked-glucosyl residues. M. tuberculosis and other mycobacterial species produce a glycogen-like α-glucan, composed of repeating units of 4-linked-glucosyl residues substituted at some positions 6 by short oligoglucosyl units, that also exhibits an anti-tumor activity. Therefore, the impression prevails that mycobacteria synthesize different types of anti-neoplastic glucans or, alternatively, the BCG substrains are singular in producing a unique type of glucan that may confer to them their immunotherapeutic property. The present study addresses this question through the comparative analysis of α-glucans purified from the extracellular materials and boiling-water extracts of three vaccine substrains. The polysaccharides were purified and their structural features were established by mono-and two-dimensional NMR spectroscopy and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry of the enzymatic and chemical degradation products of the purified compounds. The glucans isolated by the two methods from the three substrains of BCG were shown to exhibit identical structural features shared with the glycogen-like α-glucan of M. tuberculosis and other mycobacteria. Incidentally, we observed an occasional release of dextrans from Sephadex columns that may explain the reported occurrence of 6-substituted-α-glucans in mycobacteria.
structure, NMR spectroscopy, Mycobacterium, vaccine, glucan, tuberculosis
NCBI PubMed ID: 14715664Publication DOI: 10.1074/jbc.M308908200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: mamadou.daffe@ipbs.fr
Institutions: Departement Mecanismes Moleculaires des Infections Mycobacteriennes, Institut de Pharmacologie et Biologie Structurale, UMR 5089 du CNRS et de l'Universite Paul Sabatier, 205 route de Narbonne, 31077 Toulouse cedex 04, France
Methods: 13C NMR, 1H NMR, NMR-2D, GC-MS, sugar analysis, GC, RT-PCR, aminopyrene trisulfonic acid derivatization
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13. Compound ID: 1876
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a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
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a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-2)-+ | P-7)-+
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Subst-(?-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-6)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-7)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
Subst = Lewis (x/y) antigen-O-antigen |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_136044,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158538,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 614
Aspinall GO, Monteiro MA, Shaver RT, Kurjanczyk LA, Penner JL "Lipopolysaccharides of Helicobacter pylori serogroups O:3 and O:6. Structures of a class of lipopolysaccharides with reference to the location of oligomeric units of D-glycero-a-D-manno-heptose residues" -
European Journal of Biochemistry 248 (1997) 592-601
Lipopolysaccharides (LPS) from antigenically different strains assigned to serogroups O:3 and O:6 of Helicobacter pylori were isolated as water-soluble material of high Mr and as water-insoluble gels of low M,. Chemical and spectroscopic analyses of the soluble LPS and oligosaccharides liberated from the water-insoluble gels led to proposed structures with Lewis (Le) antigen determinants terminating regular repeating units of different types, linked in turn to inner core regions of invariable structure. The O:6 LPS has two populations of related molecules with chains of 3-linked D-glycero-a-D-manno-heptose residues similar to those in the MO19 strain, one with and the other without a single terminal Lewis (LeY') epitope. In contrast, in the O:3 LPS, Lewis (LeX and LeY) epitopes terminate a partially fucosylated N-acetyllactosaminoglycan, but a heptan chain similar to that in the O:6 LPS was shown to connect the outer chains to the inner core. These LPS provide examples of the molecular mimicry of cell-surface glycoconjugates. Structural variations of LPS between strains, and differences in some aspects of structure within strains, between high Mr and low Mr LPS indicate a class of LPS whose mechanisms of biosynthesis lead to overall architectures different from those characteristic of most LPS from enteric bacteria.
Lipopolysaccharide, LPS, core, O-antigen, core oligosaccharide, molecular mimicry, Helicobacter pylori, D-glycero-D-manno-heptose, Helicobacter, molecular mimicry.
NCBI PubMed ID: 9346320Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Chemistry, York University, Toronto, Ontario, Canada, Depanment of Chemistry, York University, Toronto, Ontario, Canada, Department of Microbiology, University of Toronto, Ontario, Canada
Methods: FAB-MS
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14. Compound ID: 1898
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a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
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a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-2)-+ | P-7)-+
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Subst-(?-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-6)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-7)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
Subst = Lewis (x/y) antigen-O-antigen |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_136044,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158538,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 614
Aspinall GO, Monteiro MA, Shaver RT, Kurjanczyk LA, Penner JL "Lipopolysaccharides of Helicobacter pylori serogroups O:3 and O:6. Structures of a class of lipopolysaccharides with reference to the location of oligomeric units of D-glycero-a-D-manno-heptose residues" -
European Journal of Biochemistry 248 (1997) 592-601
Lipopolysaccharides (LPS) from antigenically different strains assigned to serogroups O:3 and O:6 of Helicobacter pylori were isolated as water-soluble material of high Mr and as water-insoluble gels of low M,. Chemical and spectroscopic analyses of the soluble LPS and oligosaccharides liberated from the water-insoluble gels led to proposed structures with Lewis (Le) antigen determinants terminating regular repeating units of different types, linked in turn to inner core regions of invariable structure. The O:6 LPS has two populations of related molecules with chains of 3-linked D-glycero-a-D-manno-heptose residues similar to those in the MO19 strain, one with and the other without a single terminal Lewis (LeY') epitope. In contrast, in the O:3 LPS, Lewis (LeX and LeY) epitopes terminate a partially fucosylated N-acetyllactosaminoglycan, but a heptan chain similar to that in the O:6 LPS was shown to connect the outer chains to the inner core. These LPS provide examples of the molecular mimicry of cell-surface glycoconjugates. Structural variations of LPS between strains, and differences in some aspects of structure within strains, between high Mr and low Mr LPS indicate a class of LPS whose mechanisms of biosynthesis lead to overall architectures different from those characteristic of most LPS from enteric bacteria.
Lipopolysaccharide, LPS, core, O-antigen, core oligosaccharide, molecular mimicry, Helicobacter pylori, D-glycero-D-manno-heptose, Helicobacter, molecular mimicry.
NCBI PubMed ID: 9346320Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Chemistry, York University, Toronto, Ontario, Canada, Depanment of Chemistry, York University, Toronto, Ontario, Canada, Department of Microbiology, University of Toronto, Ontario, Canada
Methods: FAB-MS
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15. Compound ID: 1899
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a-D-Glcp-(1-3)-a-D-Glcp-(1-4)-b-D-Galp-(1-7)-+
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a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-6)-a-D-Glcp-(1-2)-+ | P-7)-+
| | |
Subst-(?-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-3)-D-gro-a-D-manHepp-(1-6)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-7)-D-gro-a-D-manHepp-(1-2)-D-gro-a-D-manHepp-(1-2)-L-gro-a-D-manHepp-(1-3)-L-gro-a-D-manHepp-(1-5)-Kdo
Subst = Lewis (y) antigen-O-antigen |
Show graphically |
Structure type: oligomer
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_136044,IEDB_137472,IEDB_140088,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_158538,IEDB_190606,IEDB_2189046,IEDB_2189047,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88
The structure is contained in the following publication(s):
- Article ID: 614
Aspinall GO, Monteiro MA, Shaver RT, Kurjanczyk LA, Penner JL "Lipopolysaccharides of Helicobacter pylori serogroups O:3 and O:6. Structures of a class of lipopolysaccharides with reference to the location of oligomeric units of D-glycero-a-D-manno-heptose residues" -
European Journal of Biochemistry 248 (1997) 592-601
Lipopolysaccharides (LPS) from antigenically different strains assigned to serogroups O:3 and O:6 of Helicobacter pylori were isolated as water-soluble material of high Mr and as water-insoluble gels of low M,. Chemical and spectroscopic analyses of the soluble LPS and oligosaccharides liberated from the water-insoluble gels led to proposed structures with Lewis (Le) antigen determinants terminating regular repeating units of different types, linked in turn to inner core regions of invariable structure. The O:6 LPS has two populations of related molecules with chains of 3-linked D-glycero-a-D-manno-heptose residues similar to those in the MO19 strain, one with and the other without a single terminal Lewis (LeY') epitope. In contrast, in the O:3 LPS, Lewis (LeX and LeY) epitopes terminate a partially fucosylated N-acetyllactosaminoglycan, but a heptan chain similar to that in the O:6 LPS was shown to connect the outer chains to the inner core. These LPS provide examples of the molecular mimicry of cell-surface glycoconjugates. Structural variations of LPS between strains, and differences in some aspects of structure within strains, between high Mr and low Mr LPS indicate a class of LPS whose mechanisms of biosynthesis lead to overall architectures different from those characteristic of most LPS from enteric bacteria.
Lipopolysaccharide, LPS, core, O-antigen, core oligosaccharide, molecular mimicry, Helicobacter pylori, D-glycero-D-manno-heptose, Helicobacter, molecular mimicry.
NCBI PubMed ID: 9346320Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Institutions: Department of Chemistry, York University, Toronto, Ontario, Canada, Depanment of Chemistry, York University, Toronto, Ontario, Canada, Department of Microbiology, University of Toronto, Ontario, Canada
Methods: FAB-MS
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