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Salamone S, Guerreiro C, Cambon E, Hargreaves JM, Tarrat N, Remaud-Simeon M, Andre I, Mulard LA
Investigation on the Synthesis of Shigella flexneri Specific Oligosaccharides Using Disaccharides as Potential Transglucosylase Acceptor Substrates
Journal of Organic Chemistry 80(22) (2015)
11237-11257
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a-D-Glcp-(1-4)-+
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-2)-a-L-Rhap-(1-2)-a-L-Rhap-(1-3)-a-L-Rhap-(1-3)-b-D-GlcpNAc-(1- |
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Shigella flexneri 2a
(NCBI TaxID 42897,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Associated disease: bacillary dysentery [ICD11:
1A02 
, ICD11:
XN7HG ];
infection due to Shigella flexneri [ICD11:
XN7Y2 ]
The structure was elucidated in this paperNCBI PubMed ID: 26340432Publication DOI: 10.1021/acs.joc.5b01407Journal NLM ID: 2985193RPublisher: Columbus, OH: American Chemical Society
Correspondence: laurence.mulard
pasteur.fr
Institutions: CNRS, UMR5504, F-31400 Toulouse, France, INRA, UMR792 Ingénierie des Systèmes Biologiques et des Procédés, F-31400 Toulouse, France, Université de Toulouse, INSA,UPS,INP, LISBP, 135 Avenue de Rangueil, 31077 Toulouse, France, Institut Pasteur, Unité de Chimie des Biomolécules, 28 rue du Dr Roux, 75724, Paris Cedex 15 France, CNRS UMR 3523, Institut Pasteur, 75015 Paris, France
Chemo-enzymatic strategies hold great potential for the development of stereo- and regioselective syntheses of structurally defined bioactive oligosaccharides. Herein, we illustrate the potential of the appropriate combination of a planned chemo-enzymatic pathway and an engineered biocatalyst for the multistep synthesis of an important decasaccharide for vaccine development. We report the stepwise investigation, which led to an efficient chemical conversion of allyl α-d-glucopyranosyl-(1→4)-α-l-rhamnopyranosyl-(1→3)-2-deoxy-2-trichlor oacetamido-β-d-glucopyranoside, the product of site-specific enzymatic α-d-glucosylation of a lightly protected non-natural disaccharide acceptor, into a pentasaccharide building block suitable for chain elongation at both ends. Successful differentiation between hydroxyl groups features the selective acylation of primary alcohols and acetalation of a cis-vicinal diol, followed by a controlled per-O-benzylation step. Moreover, we describe the successful use of the pentasaccharide intermediate in the [5 + 5] synthesis of an aminoethyl aglycon-equipped decasaccharide, corresponding to a dimer of the basic repeating unit from the O-specific polysaccharide of Shigella flexneri 2a, a major cause of bacillary dysentery. Four analogues of the disaccharide acceptor were synthesized and evaluated to reach a larger repertoire of O-glucosylation patterns encountered among S. flexneri type-specific polysaccharides. New insights on the potential and limitations of planned chemo-enzymatic pathways in oligosaccharide synthesis are provided.
Shigella flexneri, O-specific polysaccharide, pentasaccharide, vaccine, glycosides, chemical synthesis, type-specific, Glucosyltransferases, Shigella flexneri 2a, chemo-enzymatic, decasaccharide
Structure type: polymer chemical repeating unit ; n=2
Location inside paper: abstract, p.11239, scheme 2, decasaccharide 5
Aglycon: aminoethyl
Compound class: O-polysaccharide
Contained glycoepitopes: IEDB_125613,IEDB_125614,IEDB_127514,IEDB_130687,IEDB_133752,IEDB_133753,IEDB_133754,IEDB_135806,IEDB_135807,IEDB_135808,IEDB_135809,IEDB_135813,IEDB_135817,IEDB_136105,IEDB_137340,IEDB_141807,IEDB_141815,IEDB_141816,IEDB_142488,IEDB_143253,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_153213,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, chemical synthesis, chemical methods, conjugation, HR-MALDI-TOF MS, glucosylation
Synthetic data: chemoenzymatic
Comments, role: dimer of the repeating unit from the O-specific polysaccharide of Sh. flexneri 2a
NCBI Taxonomy refs (TaxIDs): 42897Reference(s) to other database(s): GTC:G13476UX
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There is only one chemically distinct structure:
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Korneev KV, Arbatsky NP, Molinaro A, Palmigiano A, Shaikhutdinova RZ, Shneider MM, Pier GB, Kondakova AN, Sviriaeva EN, Sturiale L, Garozzo D, Kruglov AA, Drutskaya MS, Nedospasov SA, Knirel YA, Kuprash DV
Contribution of the lipid A acyl groups to activation of murine Toll-Like Receptor 4 by lipopolysaccharides from various pathogenic strains of Gram-negative bacteria
Frontiers in Immunology 6 (2015)
595
|
P-1)-+
|
Lau-(1-3)-3HOMyr-(1-2)-+ |
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P-4)-+ | |
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a-Kdop-(2-4)-a-Kdop-(2-6)-+ | | |
| | | |
3HOLau-(1-3)-3HOMyr-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN
| |
Lau-(1-3)-3HOLau-(1-3)-+ 3HOLau-(1-3)-+ |
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Acinetobacter baumannii 1053
(Ancestor NCBI TaxID 470,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: infection due to Acinetobacter baumannii [ICD11:
XN8LS ]
The structure was elucidated in this paperNCBI PubMed ID: 26635809Publication DOI: 10.3389/fimmu.2015.00595Journal NLM ID: 101560960Publisher: Lausanne: Frontiers Research Foundation
Correspondence: Kuprash DV <kuprash
gmail.com>; Knirel YA <yknirel
gmail.com>
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, Moscow, Russia, Biological Faculty, Lomonosov Moscow State University, Moscow, Russia, Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow, Russia, Department of Chemical Sciences, Università di Napoli Federico II, Naples, Italy, CNR Institute for Polymers Composites and Biomaterials, Catania, Italy, State Centre of Applied Microbiology and Biotechnology, Obolensk, Moscow region, Russia, Shemyakin & Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, Division of Infectious Diseases, Department of Medicine, Brigham and Women’s Hospital and Harvard Medical School, Boston, MA, USA, German Rheumatism Research Center (DRFZ), a Leibniz Institute, Berlin, Germany.
Toll-like receptor 4 (TLR4) is required for activation of innate immunity upon recognition of lipopolysaccharide (LPS) of Gram-negative bacteria. The ability of TLR4 to respond to a particular LPS species is important since insufficient activation may not prevent bacterial growth while excessive immune reaction may lead to immunopathology associated with sepsis. Here we investigated the biological activity of LPS from Burkholderia mallei that causes glanders, and from the two well-known opportunistic pathogens Acinetobacter baumannii and Pseudomonas aeruginosa (causative agents of nosocomial infections). For each bacterial strain, R-form LPS was purified by hydrophobic chromatography and the chemical structure of lipid A, an LPS structural component, was elucidated by HR-MALDI-TOF mass spectrometry. The biological activity of LPS preparations was evaluated by their ability to induce production of proinflammatory cytokines, such as IL-6 and TNF, by bone marrow-derived macrophages (BMDM). Our results demonstrate direct correlation between the biological activity of LPS from these pathogenic bacteria and the extent of their lipid A acylation.
lipid A, Gram-negative bacteria, macrophages, innate immunity, acyl chains, proinflammatory cytokines
Structure type: oligomer
Location inside paper: fig.1, p.4
Compound class: lipid A
Contained glycoepitopes: IEDB_130650,IEDB_130659,IEDB_137340,IEDB_141807,IEDB_151531,IEDB_534864
Methods: ELISA, MS/MS, biological assays, GPC, UV, RT-PCR, statistical analysis, HR-MALDI-TOF MS
Biological activity: induction of proinflammatory cytokines by LPS isolated from various bacteria
Related record ID(s): 30798, 30799
NCBI Taxonomy refs (TaxIDs): 470
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Korneev KV, Arbatsky NP, Molinaro A, Palmigiano A, Shaikhutdinova RZ, Shneider MM, Pier GB, Kondakova AN, Sviriaeva EN, Sturiale L, Garozzo D, Kruglov AA, Drutskaya MS, Nedospasov SA, Knirel YA, Kuprash DV
Contribution of the lipid A acyl groups to activation of murine Toll-Like Receptor 4 by lipopolysaccharides from various pathogenic strains of Gram-negative bacteria
Frontiers in Immunology 6 (2015)
595
|
3HOMyr-(1-3)-+
|
?%b-L-Arap4N-(1--P--1)--+ |
| |
?%b-L-Arap4N-(1--P--4)--+ | |
| | |
3HOMyr-(1-3)-3HOPam-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN
| |
3HOMyr-(1-3)-+ 3HOPam-(1-2)-+ |
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Burkholderia mallei C-5
(Ancestor NCBI TaxID 13373,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: infection due to Burkholderia mallei [ICD11:
XN6Y3 ]
The structure was elucidated in this paperNCBI PubMed ID: 26635809Publication DOI: 10.3389/fimmu.2015.00595Journal NLM ID: 101560960Publisher: Lausanne: Frontiers Research Foundation
Correspondence: Kuprash DV <kuprash
gmail.com>; Knirel YA <yknirel
gmail.com>
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, Moscow, Russia, Biological Faculty, Lomonosov Moscow State University, Moscow, Russia, Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow, Russia, Department of Chemical Sciences, Università di Napoli Federico II, Naples, Italy, CNR Institute for Polymers Composites and Biomaterials, Catania, Italy, State Centre of Applied Microbiology and Biotechnology, Obolensk, Moscow region, Russia, Shemyakin & Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, Division of Infectious Diseases, Department of Medicine, Brigham and Women’s Hospital and Harvard Medical School, Boston, MA, USA, German Rheumatism Research Center (DRFZ), a Leibniz Institute, Berlin, Germany.
Toll-like receptor 4 (TLR4) is required for activation of innate immunity upon recognition of lipopolysaccharide (LPS) of Gram-negative bacteria. The ability of TLR4 to respond to a particular LPS species is important since insufficient activation may not prevent bacterial growth while excessive immune reaction may lead to immunopathology associated with sepsis. Here we investigated the biological activity of LPS from Burkholderia mallei that causes glanders, and from the two well-known opportunistic pathogens Acinetobacter baumannii and Pseudomonas aeruginosa (causative agents of nosocomial infections). For each bacterial strain, R-form LPS was purified by hydrophobic chromatography and the chemical structure of lipid A, an LPS structural component, was elucidated by HR-MALDI-TOF mass spectrometry. The biological activity of LPS preparations was evaluated by their ability to induce production of proinflammatory cytokines, such as IL-6 and TNF, by bone marrow-derived macrophages (BMDM). Our results demonstrate direct correlation between the biological activity of LPS from these pathogenic bacteria and the extent of their lipid A acylation.
lipid A, Gram-negative bacteria, macrophages, innate immunity, acyl chains, proinflammatory cytokines
Structure type: oligomer
Location inside paper: fig.2, p.5
Compound class: lipid A
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531
Methods: ELISA, MS/MS, biological assays, GPC, UV, RT-PCR, statistical analysis, HR-MALDI-TOF MS
Biological activity: induction of proinflammatory cytokines by LPS isolated from various bacteria
Comments, role: in Fig 2. Ara4N is depicted as β-D and configurations are not discussed in the text. β-L configuration was assumed as correct
Related record ID(s): 30625, 30799
NCBI Taxonomy refs (TaxIDs): 13373
Show glycosyltransferases
There is only one chemically distinct structure:
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Korneev KV, Arbatsky NP, Molinaro A, Palmigiano A, Shaikhutdinova RZ, Shneider MM, Pier GB, Kondakova AN, Sviriaeva EN, Sturiale L, Garozzo D, Kruglov AA, Drutskaya MS, Nedospasov SA, Knirel YA, Kuprash DV
Contribution of the lipid A acyl groups to activation of murine Toll-Like Receptor 4 by lipopolysaccharides from various pathogenic strains of Gram-negative bacteria
Frontiers in Immunology 6 (2015)
595
|
3HOLau-(1-3)-3HOLau-(1-2)-+
|
P-4)-+ |
| |
3HOLau-(1-3)-3HOLau-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN
|
P-1)-+ |
Show graphically |
Pseudomonas aeruginosa 2192
(NCBI TaxID 350703,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
Host organism: Homo sapiens
Associated disease: infection due to Pseudomonas aeruginosa [ICD11:
XN5L6 ]
The structure was elucidated in this paperNCBI PubMed ID: 26635809Publication DOI: 10.3389/fimmu.2015.00595Journal NLM ID: 101560960Publisher: Lausanne: Frontiers Research Foundation
Correspondence: Kuprash DV <kuprash
gmail.com>; Knirel YA <yknirel
gmail.com>
Institutions: Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia, Belozersky Institute of Physico-Chemical Biology, Lomonosov Moscow State University, Moscow, Russia, Biological Faculty, Lomonosov Moscow State University, Moscow, Russia, Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow, Russia, Department of Chemical Sciences, Università di Napoli Federico II, Naples, Italy, CNR Institute for Polymers Composites and Biomaterials, Catania, Italy, State Centre of Applied Microbiology and Biotechnology, Obolensk, Moscow region, Russia, Shemyakin & Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Moscow, Russia, Division of Infectious Diseases, Department of Medicine, Brigham and Women’s Hospital and Harvard Medical School, Boston, MA, USA, German Rheumatism Research Center (DRFZ), a Leibniz Institute, Berlin, Germany.
Toll-like receptor 4 (TLR4) is required for activation of innate immunity upon recognition of lipopolysaccharide (LPS) of Gram-negative bacteria. The ability of TLR4 to respond to a particular LPS species is important since insufficient activation may not prevent bacterial growth while excessive immune reaction may lead to immunopathology associated with sepsis. Here we investigated the biological activity of LPS from Burkholderia mallei that causes glanders, and from the two well-known opportunistic pathogens Acinetobacter baumannii and Pseudomonas aeruginosa (causative agents of nosocomial infections). For each bacterial strain, R-form LPS was purified by hydrophobic chromatography and the chemical structure of lipid A, an LPS structural component, was elucidated by HR-MALDI-TOF mass spectrometry. The biological activity of LPS preparations was evaluated by their ability to induce production of proinflammatory cytokines, such as IL-6 and TNF, by bone marrow-derived macrophages (BMDM). Our results demonstrate direct correlation between the biological activity of LPS from these pathogenic bacteria and the extent of their lipid A acylation.
lipid A, Gram-negative bacteria, macrophages, innate immunity, acyl chains, proinflammatory cytokines
Structure type: oligomer
Location inside paper: fig.3, p.6
Compound class: lipid A
Contained glycoepitopes: IEDB_137340,IEDB_141807,IEDB_151531
Methods: ELISA, MS/MS, biological assays, GPC, UV, RT-PCR, statistical analysis, HR-MALDI-TOF MS
Biological activity: induction of proinflammatory cytokines by LPS isolated from various bacteria
Related record ID(s): 30625, 30798
NCBI Taxonomy refs (TaxIDs): 350703
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There is only one chemically distinct structure:
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