Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_141794,IEDB_141798,IEDB_153201,IEDB_156493,IEDB_190606,IEDB_225177,IEDB_885823,SB_165,SB_166,SB_187,SB_195,SB_7,SB_88

• Article ID: 25
  Bubb WA, Urashima T, Fujiwara R, Shinnai T, Ariga H "Structural characterization of the extracellular polysaccharide produced by Streptococcus thermophilus OR 901" - Carbohydrate Research 301(1-2) (1997) 41-50
  

  The exocellular polysaccharide of Streptococcus thermophilus OR 901, isolated from partially deproteinised whey, is a heteropolymer of D-galactopyranose and L-rhamnopyranose residues in the molar ratio 5:2. The structure was established by methylation analysis and 1D and 2D NMR spectroscopy of the native polysaccharide, in combination with characterisation of oligosaccharide fragments, obtained by partial acid hydrolysis, using methylation analysis and 1D 1H NMR spectroscopy. The polysaccharide has a branched heptasaccharide repeating unit with the following structure: [structure]

  Lactic acid bacteria, Streptococcus thermophilus, Exopolysaccharide structure, NMR data

  NCBI PubMed ID: 9228738
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: wab@biochem.usyd.edu.au
  Institutions: Department of Biochemistry, University of Sydney, NSW, Australia
  Methods: 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, acid hydrolysis
  
   
  
  Streptococcus thermophilus OR901
  CSDB ID 1807 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_115136,IEDB_130422,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_140630,IEDB_141798,IEDB_141807,IEDB_151531,IEDB_225177,IEDB_885823

• Article ID: 28
  Bystrova OV, Zatonsky GV, Borisova SA, Kocharova NA, Shashkov AS, Knirel YA, Kholodkova EV, Stanislavsky ES "Structure of an acidic O-specific polysaccharide of the bacterium Providencia alcalifaciens O7" - Biochemistry (Moscow) 65(6) (2000) 677-684
  

  An acidic O-specific polysaccharide was obtained by mild acid degradation of the lipopolysaccharide of the bacterium Providencia alcalifaciens O7 and purified by gel chromatography followed by anion-exchange chromatography. On the basis of full acid hydrolysis, methylation, carboxyl reduction, selective cleavage with anhydrous hydrogen fluoride, and 1H- and 13C NMR spectroscopy, including two-dimensional 1H,1H homonuclear and H-detected 1H,13C het-eronuclear correlation spectroscopy and nuclear Overhauser effect spectroscopy (NOESY), the following structure of the linear tetrasaccharide repeating unit of the polysaccharide was established: →4)-p-D-GlcpNAc-(l→3)-a-D-GlcpA-(l→4)-a-D-GlcpNAc-(l→3)-p-L-Rhap2Ac-(1→ where Rhap2Ac is 2-O-acetylrhamnopyranose

  Lipopolysaccharide, LPS, structure, polysaccharide, O-antigen, acidic, bacteria, neutral, O-specific, O-specific polysaccharide, Providencia, Providencia alcalifaciens

  NCBI PubMed ID: 10887286
  Journal NLM ID: 0376536
  Publisher: Nauka/Interperiodica
  Correspondence: knirel@ioc.ac.ru
  Institutions: N.D.Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Mechnikov Central Research Institute of Vaccines and Sera, Russian Ministry of Public Health, Pereulok Mechnikova 5a, Moscow, 103064 Russia
  Methods: 13C NMR, 1H NMR, NMR-2D, GLC-MS, HF solvolysis, GLC, carboxyl reduction, anion-exchange chromatography
  
   
  
  Providencia alcalifaciens O7
  CSDB ID 1811 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_125613,IEDB_125614,IEDB_133754,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_141798,IEDB_141807,IEDB_141815,IEDB_143253,IEDB_151531,IEDB_153213,IEDB_225177,IEDB_885823

• Article ID: 205
  Vyas NK, Vyas MN, Chervenak MC, Johnson MA, Pinto BM, Bundle DR, Quiocho FA "Molecular recognition of oligosaccharide epitopes by a monoclonal fab specific for Shigella flexneri Y lipopolysaccharide: X-ray structures and thermodynamics" - Biochemistry 41(46) (2002) 13575-13586
  

  The antigenic recognition of Shigella flexneri O-polysaccharide, which consists of a repeating unit ABCD [→2)-α-L-Rhap-(1→2)-α-L-Rhap-(1→3)-α-L-Rhap-(1→3)-β-D-GlcpNAc-(1→], by the monoclonal antibody SYA/J6 (IgG3, kappa) has been investigated by crystallographic analysis of the Fab domain and its two complexes with two antigen segments (a pentasaccharide Rha A-Rha B-Rha C-GlcNAc D-Rha A' and a modified trisaccharide Rha B-Rha C-GlcNAc D in which Rha C is missing a C2-OH group). These complex structures, the first for a Fab specific for a periodic linear heteropolysaccharide, reveal a binding site groove (between the V(H) and V(L) domains) that makes polar and nonpolar contacts with all the sugar

  Lipopolysaccharide, antigen, oligosaccharide, structure, repeating unit, trisaccharide, analysis, antigenic, group, molecular, X-ray, Shigella flexneri, antibodies, antibody, epitope, monoclonal, monoclonal antibodies, monoclonal antibody, recognition, complex, epitopes, O-polysaccharide, O polysaccharide, specific, sugar, modified, Shigella, pentasaccharide, binding, binding site, domain, domains, FAB, heteropolysaccharide, linear, molecular recognition, polar, site, thermodynamics

  NCBI PubMed ID: 12427018
  Journal NLM ID: 0370623
  Publisher: American Chemical Society
  Correspondence: faq@bcm.tmc.edu
  Institutions: Verna and Marrs Mclean Department of Biochemistry and Molecular Biology and Howard Hughes Medical Institute, Baylor College of Medicine, Houston, Texas 77030, Departments of Chemistry and of Molecular Biology and Biochemistry, Simon Fraser University, Burnaby, British Columbia, Canada V5A 1S6, Department of Chemistry, University of Alberta, Edmonton, AB, Canada
  Methods: crystallography, thermodynamics
  
   
  
  Shigella flexneri
  CSDB ID 5723 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_136105,IEDB_141798,IEDB_225177,IEDB_885813,IEDB_885823

• Article ID: 279
  Kaji E, Anabuki N, Zen S "Syntheses of three interglycosidic isomers of N-acetyl-b-D-mannosaminyl-L-rhamnoses associated with O-antigens of several gram-negative opportunistic pathogens" - Chemical and Pharmaceutical Bulletin 43 (1995) 1441-1447
  

  We achieved practical, highly stereoselective syntheses of three interglycosidic isomers of N-acetyl-β-D-mannosaminyl-L-rhamnoses, among which a β(1→4)-isomer corresponds to the repeating unit of the O-antigen of lipopolysaccharide (LPS) from the opportunistic pathogens Pseudomonas cepacia O5 and Pseudomonas aeruginosa X (Meitert). The other isomers are a β(1→2)-disaccharide, a constituent of LPS from Escherichia coli O1A, and an artificial β(1→3)-isomer. The disaccharides were obtained by simple three-step reaction sequences from 2-(benzoyloxyimino)-2-deoxyglycosyl halides (mannosamine progenitor). β-Selective glycosylations of appropriately protected L-rhamnosyl acceptors were performed. Subsequent reduction of the 2-acyloxyimino function to an amino group, N-acetylation, and removal of the protecting groups provided the target disaccharides. 13C NMR and nuclear Overhauser effect spectra proved to be useful for structural determination of the positional isomers of the disaccharides.

  Lipopolysaccharide, O-antigen, Gram-negative bacteria, 2-amino-2-deoxy-D-mannose, β-3-D-mannosaminyl-L-rhamnose, 2-uiose oxime, opportunistic infection

  NCBI PubMed ID: 7586068
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: School of Pharmaceutical Sciences, Kiiasaw University, Shirokane 5-9-1, Minato-ku, Tokyo IDS, Japan, School of Pharmaceutical Sciences, Kiiasaw University, Shirokane 5-9-1, Minato-ku, Tokyo IDS, Japan.
  
   
  
  Pseudomonas cepacia O5, Pseudomonas aeruginosa X (Meitert)
  CSDB ID 7220 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_136105,IEDB_141798,IEDB_225177,IEDB_885813,IEDB_885823

• Article ID: 279
  Kaji E, Anabuki N, Zen S "Syntheses of three interglycosidic isomers of N-acetyl-b-D-mannosaminyl-L-rhamnoses associated with O-antigens of several gram-negative opportunistic pathogens" - Chemical and Pharmaceutical Bulletin 43 (1995) 1441-1447
  

  We achieved practical, highly stereoselective syntheses of three interglycosidic isomers of N-acetyl-β-D-mannosaminyl-L-rhamnoses, among which a β(1→4)-isomer corresponds to the repeating unit of the O-antigen of lipopolysaccharide (LPS) from the opportunistic pathogens Pseudomonas cepacia O5 and Pseudomonas aeruginosa X (Meitert). The other isomers are a β(1→2)-disaccharide, a constituent of LPS from Escherichia coli O1A, and an artificial β(1→3)-isomer. The disaccharides were obtained by simple three-step reaction sequences from 2-(benzoyloxyimino)-2-deoxyglycosyl halides (mannosamine progenitor). β-Selective glycosylations of appropriately protected L-rhamnosyl acceptors were performed. Subsequent reduction of the 2-acyloxyimino function to an amino group, N-acetylation, and removal of the protecting groups provided the target disaccharides. 13C NMR and nuclear Overhauser effect spectra proved to be useful for structural determination of the positional isomers of the disaccharides.

  Lipopolysaccharide, O-antigen, Gram-negative bacteria, 2-amino-2-deoxy-D-mannose, β-3-D-mannosaminyl-L-rhamnose, 2-uiose oxime, opportunistic infection

  NCBI PubMed ID: 7586068
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: School of Pharmaceutical Sciences, Kiiasaw University, Shirokane 5-9-1, Minato-ku, Tokyo IDS, Japan, School of Pharmaceutical Sciences, Kiiasaw University, Shirokane 5-9-1, Minato-ku, Tokyo IDS, Japan.
  
   
  
  Escherichia coli O1A
  CSDB ID 7223 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_136105,IEDB_141798,IEDB_225177,IEDB_885813,IEDB_885823

• Article ID: 279
  Kaji E, Anabuki N, Zen S "Syntheses of three interglycosidic isomers of N-acetyl-b-D-mannosaminyl-L-rhamnoses associated with O-antigens of several gram-negative opportunistic pathogens" - Chemical and Pharmaceutical Bulletin 43 (1995) 1441-1447
  

  We achieved practical, highly stereoselective syntheses of three interglycosidic isomers of N-acetyl-β-D-mannosaminyl-L-rhamnoses, among which a β(1→4)-isomer corresponds to the repeating unit of the O-antigen of lipopolysaccharide (LPS) from the opportunistic pathogens Pseudomonas cepacia O5 and Pseudomonas aeruginosa X (Meitert). The other isomers are a β(1→2)-disaccharide, a constituent of LPS from Escherichia coli O1A, and an artificial β(1→3)-isomer. The disaccharides were obtained by simple three-step reaction sequences from 2-(benzoyloxyimino)-2-deoxyglycosyl halides (mannosamine progenitor). β-Selective glycosylations of appropriately protected L-rhamnosyl acceptors were performed. Subsequent reduction of the 2-acyloxyimino function to an amino group, N-acetylation, and removal of the protecting groups provided the target disaccharides. 13C NMR and nuclear Overhauser effect spectra proved to be useful for structural determination of the positional isomers of the disaccharides.

  Lipopolysaccharide, O-antigen, Gram-negative bacteria, 2-amino-2-deoxy-D-mannose, β-3-D-mannosaminyl-L-rhamnose, 2-uiose oxime, opportunistic infection

  NCBI PubMed ID: 7586068
  Journal NLM ID: 0377775
  Publisher: Pharmaceutical Society Of Japan
  Institutions: School of Pharmaceutical Sciences, Kiiasaw University, Shirokane 5-9-1, Minato-ku, Tokyo IDS, Japan, School of Pharmaceutical Sciences, Kiiasaw University, Shirokane 5-9-1, Minato-ku, Tokyo IDS, Japan.
  
   
  
  (bacteria)
  CSDB ID 7224 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: CPS
Contained glycoepitopes: IEDB_115136,IEDB_136044,IEDB_136105,IEDB_137472,IEDB_137485,IEDB_140630,IEDB_141794,IEDB_141798,IEDB_144983,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,SB_165,SB_166,SB_187,SB_195,SB_44,SB_7,SB_72,SB_88

• Article ID: 649
  Gloaguen V, Morvan H, Hoffmann L, Plancke Y, Wieruszeski J, Lippens G, Strecker G "Capsular polysaccharide produced by the thermophilic cyanobacterium Mastigocladus laminosus: Structural study of an undecasaccharide obtained by lithium degradation" - European Journal of Biochemistry 266 (1999) 762-770
  

  The capsular polysaccharide produced by the thermophilic cyanobacterium Mastigocladus laminosus has been subjected to a specific degradation with lithium in ethylenediamine. The released undecasaccharide attached to one unit of tetrahydroxycyclopentanecarboxylic acid has been characterized by a combination of 2D nuclear magnetic resonance spectroscopy, mass spectrometry, monosaccharidic composition and linkage analyses. From the overlap of the structure of this oligosaccharide with previously identified di-, tri- and pentasaccharides released by mild acid hydrolysis, the capsular polysaccharide was deduced to have a pentadecasaccharide repeating unit with the following structure:

  NMR, structure, exopolysaccharide, cyanobacterium, lithium degradation

  NCBI PubMed ID: 10583369
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  Correspondence: vgloaguen@unilim.fr
  Institutions: Equipe de Glycobiologie Vegetale, Institut de Biotechnologie, Université de Limoges, Limoges, France, Cellule de Recherche en Environnement et Biotechnologies, CRP-Centre Universitaire, Luxembourg, Institut de Botanique, Universite de Liege, Liege, Belgium, Laboratoire de Chimie biologique, UMR 111 (CNRS), Universite des Sciences et Techniques Lille Flandres-Artois, France, Centre National de la Recherche Scientifique, URA 1309, Institut Pasteur de Lille, France
  Methods: NMR-2D, NMR, mild acid hydrolysis, MS, Li/ethylenediamine degradation
  
   
  
  Mastigocladus laminosus
  CSDB ID 569 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: repeating unit of the O-polysaccharide
Contained glycoepitopes: IEDB_130648,IEDB_135813,IEDB_136105,IEDB_137340,IEDB_137473,IEDB_1391961,IEDB_1391965,IEDB_141582,IEDB_141584,IEDB_141798,IEDB_141807,IEDB_151531,IEDB_225177,IEDB_423113,IEDB_885822,IEDB_885823

• Article ID: 917
  Landersjo C, Widmalm G "Solution structure of a pentasaccharide representing the repeating unit of the O-antigen polysaccharide from Escherichia coli O142: NMR spectroscopy and molecular simulation studies" - Biopolymers 64(6) (2002) 283-291
  

  Conformational studies have been performed of a pentasaccharide derived from the O-polysaccharide from Escherichia coli O142. The polymer was selectively degraded by anhydrous hydrogen fluoride and reduced to yield an oligosaccharide model of its repeating unit, which in the branching region consists of four aminosugars. A comparison of (1)H and (13)C chemical shifts between the pentasaccharide and the polymer showed only minor differences, except where the cleavage had taken place, indicating that the oligomer is a good model of the repeating unit. Langevin dynamics and molecular dynamics simulations with explicit water molecules were carried out to sample the conformational space of the pentasaccharide. For the glycosidic linkages between the hexopyranoside residues, small but significant changes were observed between the simulation techniques. One-dimensional (1D) (1)H,(1)H double pulsed field gradient spin echo (DPFGSE) transverse rotating- frame Overhauser effect spectroscopy (T-ROESY) experiments were performed, and homonuclear cross-relaxation rates were obtained. Subsequently, a comparison of interproton distances from NMR experiment and the two simulation approaches showed that in all cases the use of explicit water in the simulations resulted in better agreement. Hydrogen-bond analysis of the trajectories from the molecular dynamics simulation revealed interresidue interactions to be important as a cluster of different hydrogen bonds and as a distinct highly populated hydrogen bond. NMR data are consistent with the presence of hydrogen bonding within the model of the repeating unit

  NMR, oligosaccharide, structure, chemistry, polysaccharide, O-antigen, repeating unit, analysis, O antigen, hydrogen, hydrogen bond, molecular, molecule, polymer, water, Escherichia, Escherichia coli, glycosidic linkage, conformational, dynamics, molecular dynamics, NMR spectroscopy, cluster, O-polysaccharide, O polysaccharide, linkage, chemical, region, reduced, spectroscopy, interaction, difference, pentasaccharide, comparison, solution, case, change, simulation, effect, Overhauser effect, organic, model, use, cleavage, approach, chemical shift, chemical shifts, distance, Hydrogen Bonding, hydrogen fluoride, Langevin dynamics, rotating frame, shift

  NCBI PubMed ID: 12124846
  Journal NLM ID: 0372525
  Publisher: Wiley Interscience
  Correspondence: G. Widmalm
  Institutions: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden
  Methods: NMR-2D, NMR, MS, MD simulations, solvolysis
  
   
  
  Escherichia coli O142
  CSDB ID 3209 (all data & tools)

Show legend Show as text

Structure type: oligomer ; n=2
Contained glycoepitopes: IEDB_125611,IEDB_130668,IEDB_130669,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141798,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7

• Article ID: 1116
  Pozsgay V "Synthesis of a hexadecasaccharide fragment of the O-polysaccharide of Shigella dysenteriae type 1" - Journal of the American Chemical Society 117 (1995) 6673-6681
  

  A synthetic route is described to a hexadecasaccharide fragment of the O-polysaccharide portion of the lipopolysaccharide of Shigella dysenteriae type 1, a Gram-negative human pathogen. The key intermediate was a trichloroacetimidate derivative of the tetrasaccharide Rha α1→2 Gal α1→3 GlcNAc α1→3 Rha α1→3 (23) which corresponds to a complete repeating unit of this polysaccharide. Important stages involved the stereoselective construction of a GlcNAc α1→3 Rha synthon (7) which was transformed into a glycosyl acceptor (13) that was α-galactosylated in a stereocontrolled reaction with a thiogalactoside donor (14). Conversion of the Gal α1→3 GlcNAc α1→3 Rha intermediate 15 into the glycosyl acceptor 17 followed be stereoselective α-rhamnosylation afforded the fully protected terasaccharide glycoside from which the tetrasaccharide donor 23 was prepared that contains a selectively removable, benzyl protecting group at the site of the chain extension. The donor was first coupled with 1-decanol to give the tetrasaccharide glycoside 24. One-step conversion provided the tetrasaccharide acceptor 25. Subsequent, iterative glycosylations with the donor 23, used in excess, afforded the fully protected octa-, dodeca-, and hexadecasaccharides, conventional deprotection of which led to di- (2), tri- (3), and tetrameric (4) repeating units of the O-polysaccharide of Sh. dysentriiae type 1.

  Lipopolysaccharide, synthesis, hexasaccharide, polysaccharide, O-specific, Shigella dysenteriae type 1, Shigella dysenteriae

  Publication DOI: 10.1021/ja00130a004
  Journal NLM ID: 7503056
  Publisher: American Chemical Society
  Institutions: Contribution from the Laboratory of Developmental and Molecular Immunity, National Institute of Child Health and Human Development, National Institutes of Health, Bethesda, MD, USA
  
   
  
  Shigella dysenteriae 1
  CSDB ID 4075 (all data & tools)

Show legend Show as text

Structure type: oligomer ; n=3
Contained glycoepitopes: IEDB_125611,IEDB_130668,IEDB_130669,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_141798,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7

• Article ID: 1116
  Pozsgay V "Synthesis of a hexadecasaccharide fragment of the O-polysaccharide of Shigella dysenteriae type 1" - Journal of the American Chemical Society 117 (1995) 6673-6681
  

  A synthetic route is described to a hexadecasaccharide fragment of the O-polysaccharide portion of the lipopolysaccharide of Shigella dysenteriae type 1, a Gram-negative human pathogen. The key intermediate was a trichloroacetimidate derivative of the tetrasaccharide Rha α1→2 Gal α1→3 GlcNAc α1→3 Rha α1→3 (23) which corresponds to a complete repeating unit of this polysaccharide. Important stages involved the stereoselective construction of a GlcNAc α1→3 Rha synthon (7) which was transformed into a glycosyl acceptor (13) that was α-galactosylated in a stereocontrolled reaction with a thiogalactoside donor (14). Conversion of the Gal α1→3 GlcNAc α1→3 Rha intermediate 15 into the glycosyl acceptor 17 followed be stereoselective α-rhamnosylation afforded the fully protected terasaccharide glycoside from which the tetrasaccharide donor 23 was prepared that contains a selectively removable, benzyl protecting group at the site of the chain extension. The donor was first coupled with 1-decanol to give the tetrasaccharide glycoside 24. One-step conversion provided the tetrasaccharide acceptor 25. Subsequent, iterative glycosylations with the donor 23, used in excess, afforded the fully protected octa-, dodeca-, and hexadecasaccharides, conventional deprotection of which led to di- (2), tri- (3), and tetrameric (4) repeating units of the O-polysaccharide of Sh. dysentriiae type 1.

  Lipopolysaccharide, synthesis, hexasaccharide, polysaccharide, O-specific, Shigella dysenteriae type 1, Shigella dysenteriae

  Publication DOI: 10.1021/ja00130a004
  Journal NLM ID: 7503056
  Publisher: American Chemical Society
  Institutions: Contribution from the Laboratory of Developmental and Molecular Immunity, National Institute of Child Health and Human Development, National Institutes of Health, Bethesda, MD, USA
  
   
  
  Shigella dysenteriae 1
  CSDB ID 4284 (all data & tools)

Show legend Show as text

Structure type: oligomer ; n=4
Contained glycoepitopes: IEDB_125611,IEDB_130668,IEDB_130669,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_137483,IEDB_141794,IEDB_141798,IEDB_141807,IEDB_151528,IEDB_151531,IEDB_190606,IEDB_225177,IEDB_885823,SB_7

• Article ID: 1116
  Pozsgay V "Synthesis of a hexadecasaccharide fragment of the O-polysaccharide of Shigella dysenteriae type 1" - Journal of the American Chemical Society 117 (1995) 6673-6681
  

  A synthetic route is described to a hexadecasaccharide fragment of the O-polysaccharide portion of the lipopolysaccharide of Shigella dysenteriae type 1, a Gram-negative human pathogen. The key intermediate was a trichloroacetimidate derivative of the tetrasaccharide Rha α1→2 Gal α1→3 GlcNAc α1→3 Rha α1→3 (23) which corresponds to a complete repeating unit of this polysaccharide. Important stages involved the stereoselective construction of a GlcNAc α1→3 Rha synthon (7) which was transformed into a glycosyl acceptor (13) that was α-galactosylated in a stereocontrolled reaction with a thiogalactoside donor (14). Conversion of the Gal α1→3 GlcNAc α1→3 Rha intermediate 15 into the glycosyl acceptor 17 followed be stereoselective α-rhamnosylation afforded the fully protected terasaccharide glycoside from which the tetrasaccharide donor 23 was prepared that contains a selectively removable, benzyl protecting group at the site of the chain extension. The donor was first coupled with 1-decanol to give the tetrasaccharide glycoside 24. One-step conversion provided the tetrasaccharide acceptor 25. Subsequent, iterative glycosylations with the donor 23, used in excess, afforded the fully protected octa-, dodeca-, and hexadecasaccharides, conventional deprotection of which led to di- (2), tri- (3), and tetrameric (4) repeating units of the O-polysaccharide of Sh. dysentriiae type 1.

  Lipopolysaccharide, synthesis, hexasaccharide, polysaccharide, O-specific, Shigella dysenteriae type 1, Shigella dysenteriae

  Publication DOI: 10.1021/ja00130a004
  Journal NLM ID: 7503056
  Publisher: American Chemical Society
  Institutions: Contribution from the Laboratory of Developmental and Molecular Immunity, National Institute of Child Health and Human Development, National Institutes of Health, Bethesda, MD, USA
  
   
  
  Shigella dysenteriae 1
  CSDB ID 4275 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: repeating unit of the O-antigenic polysaccharide
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_141798,IEDB_144825,IEDB_225177,IEDB_885823

• Article ID: 1325
  Zhang J, Zhu Y, Kong F "Synthesis of an L-rhamnose tetrasaccharide, the common and major structure of the repeating unit of the O-antigenic polysaccharide of a strain of Klebsiella pneumoniae and Pseudomonas holci" - Carbohydrate Research 336(3) (2001) 229-235
  

  A tetrasaccharide, α-L-Rhap-(1→3)-α-L-Rhap-(1→2)-α-L-Rhap-(1→2)-L-Rhap, the common and major structure of the repeating unit of the O-antigenic polysaccharide of a strain of Klebsiella pneumoniae and Pseudomonas holci was synthesized as its methyl and octyl glycosides. Selective 3-O-glycosylation of allyl α-L-rhamnopyranoside with 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl trichloroacetimidate gave allyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→3)-α-L-rhamnopyranoside (3). Benzoylation, deallylation, and trichloroacetimidation afforded 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate (6). Self condensation of 3,4-di-O- benzoyl-β-L-rhamnopyranose 1,2-methyl orthoester or 1,2-octyl orthoester gave methyl or octyl 2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1→2)-3,4-di-O-benzoyl-α-L-rhamnopyranoside (16 or 17), and subsequent selective deacetylation gave the disaccharide acceptor (18 or 19). Coupling of 6 with 18 (or 19), followed by deacylation in ammonia-saturated methanol, produced the target tetrasacharide

  antigen, oligosaccharide, rhamnose

  NCBI PubMed ID: 11705472
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: fzkong@mail.rcees.ac.cn
  Institutions: Research Center for Eco-Environmental Sciences, Academia Sinica, PO Box 2871, Beijing 100085, PR China
  
   
  
  Klebsiella pneumoniae, Pseudomonas holci
  CSDB ID 5970 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_136105,IEDB_141798,IEDB_225177,IEDB_885823

• Article ID: 1326
  Zhang J, Kong F "Synthesis of an xylosylated rhamnose pentasaccharide, the repeating unit of the O-chain polysaccharide of the lipopolysaccharide of Xanthomonas campestris pv. begoniae GSPB 525" - Carbohydrate Research 337(5) (2002) 391-396
  

  A xylosylated rhamnose pentasaccharide, α-L-Rhap-(1→3)-[β-L-Xylp-(1→2)-]-α-L-Rhap-(1→3)-[β-L-Xylp-(1→4)]-L-Rhap, the repeating unit of the O-chain polysaccharide (OPS) of the lipopolysaccharides of Xanthomonas campestris pv. begoniae GSPB 525 was synthesized by a highly regio- and stereoselective way. Thus coupling of 1,2-O-ethylidene-β-L-rhamnopyranose (1) with 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate (2) to give (1→3)-linked disaccharide (3), subsequent benzoylation, deethylidenation, acetylation, 1-O- deacetylation, and trichloroacetimidation afforded the disaccharide donor 11. Condensation of 11 with 1 yielded 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-2-O-acetyl-4-O-benzoyl-α-L-rhamnopyranosyl-(1→3)-1,2-O-ethylidene-β-L-rhamnopyranose (12), and selective deacetylation of 12 yielded the trisaccharide diol acceptor 15. Coupling of 15 with 2,3,4-tri-O-benzoyl-α-L-xylopyranosyl trichloroacetimidate (16), followed by deprotection, gave the target pentasaccharide 19

  Lipopolysaccharide, synthesis, lipopolysaccharides, polysaccharide, repeating unit, trisaccharide, Research, O-chain, pentasaccharide, rhamnose, disaccharide, acceptor, Xanthomonas, acetylation, Xanthomonas campestris, stereoselective, coupling, target, condensation, deacetylation, selective

  NCBI PubMed ID: 11861012
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: fzkong@mail.rcees.ac.cn
  Institutions: Research Center for Eco-Environmental Sciences, Academia Sinica, PO Box 2871, 100085, Beijing, PR China
  
   
  
  Xanthomonas campestris pv. begoniae
  CSDB ID 6169 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_115136,IEDB_136105,IEDB_140630,IEDB_141798,IEDB_225177,IEDB_423153,IEDB_885823

• Article ID: 1304
  Yun Yang B, Gray JSS, Montgomery R "Extracellular polysaccharide of Erwinia chrysanthemi CU643" - Carbohydrate Research 316(1-4) (1999) 138-154
  

  Erwinia chrysanthemi are gram-negative bacterial phytopathogens causing soft rots in a number of plants. The structure of the extracellular polysaccharide (EPS) produced by E. chrysanthemi strain CU643, pathogenic to Philodendron, has been determined using a combination of chemical and physical techniques including methylation analysis, high- and low-pressure gel-filtration and anion-exchange chromatography, high-pH anion-exchange chromatography, partial acid hydrolysis, mass spectrometry, and 1- and 2-D NMR spectroscopy. In contrast to the structures of the EPS reported for other strains of E. chrysanthemi, the EPS from strain CU643 is a linear polysaccharide containing L-Rhap, D-Galp, and D-GlcAp in the ratio 4:1:1. Evidence is presented for the following hexasaccharide repeat unit [see text]

  structure, extracellular polysaccharide, Erwinia chrysanthemi, Philodendron

  NCBI PubMed ID: 10420593
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: rex-montgomery@uiowa.edu
  Institutions: Department of Biochemistry, College of Medicine, University of Iowa, Iowa City 52242, USA
  Methods: NMR-2D, methylation, FAB-MS, partial acid hydrolysis, NMR, MALDI-TOF MS
  
   
  
  Erwinia chrysanthemi CU643
  CSDB ID 6052 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_115136,IEDB_133754,IEDB_136105,IEDB_140630,IEDB_141798,IEDB_225177,IEDB_423153,IEDB_885823

• Article ID: 1304
  Yun Yang B, Gray JSS, Montgomery R "Extracellular polysaccharide of Erwinia chrysanthemi CU643" - Carbohydrate Research 316(1-4) (1999) 138-154
  

  Erwinia chrysanthemi are gram-negative bacterial phytopathogens causing soft rots in a number of plants. The structure of the extracellular polysaccharide (EPS) produced by E. chrysanthemi strain CU643, pathogenic to Philodendron, has been determined using a combination of chemical and physical techniques including methylation analysis, high- and low-pressure gel-filtration and anion-exchange chromatography, high-pH anion-exchange chromatography, partial acid hydrolysis, mass spectrometry, and 1- and 2-D NMR spectroscopy. In contrast to the structures of the EPS reported for other strains of E. chrysanthemi, the EPS from strain CU643 is a linear polysaccharide containing L-Rhap, D-Galp, and D-GlcAp in the ratio 4:1:1. Evidence is presented for the following hexasaccharide repeat unit [see text]

  structure, extracellular polysaccharide, Erwinia chrysanthemi, Philodendron

  NCBI PubMed ID: 10420593
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: rex-montgomery@uiowa.edu
  Institutions: Department of Biochemistry, College of Medicine, University of Iowa, Iowa City 52242, USA
  Methods: NMR-2D, methylation, FAB-MS, partial acid hydrolysis, NMR, MALDI-TOF MS
  
   
  
  Erwinia chrysanthemi CU643
  CSDB ID 6053 (all data & tools)