About: Rational Design and Synthesis of Optimized Glycoclusters for Multivalent Lectin-Carbohydrate Interactions: Influence of the Linker Arm     Goto   Sponge   NotDistinct   Permalink

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Description
  • The design of multivalent glycoclusters requires the conjugation of biologically relevant carbohydrate epitopes functionalized with linker arms to multivalent core scaffolds. The multigram-scale syntheses of three structurally modified triethyleneglycol analogues that incorporate amide moiety(ies) and/or a phenyl ring offer convenient access to a series of carbohydrate probes with different water solubilities and rigidities. Evaluation of flexibility and determination of preferred conformations were performed by conformational analysis. Conjugation of the azido-functionalized carbohydrates with tetra-propargylated core scaffolds afforded a library of 18 tetravalent glycoclusters, in high yields, by CuI-catalyzed azidealkyne cycloaddition (CuAAC). The compounds were evaluated for their ability to bind to PA-IL (the LecA lectin from the opportunistic pathogen Pseudomonas aeruginosa).
  • The design of multivalent glycoclusters requires the conjugation of biologically relevant carbohydrate epitopes functionalized with linker arms to multivalent core scaffolds. The multigram-scale syntheses of three structurally modified triethyleneglycol analogues that incorporate amide moiety(ies) and/or a phenyl ring offer convenient access to a series of carbohydrate probes with different water solubilities and rigidities. Evaluation of flexibility and determination of preferred conformations were performed by conformational analysis. Conjugation of the azido-functionalized carbohydrates with tetra-propargylated core scaffolds afforded a library of 18 tetravalent glycoclusters, in high yields, by CuI-catalyzed azidealkyne cycloaddition (CuAAC). The compounds were evaluated for their ability to bind to PA-IL (the LecA lectin from the opportunistic pathogen Pseudomonas aeruginosa). (en)
Title
  • Rational Design and Synthesis of Optimized Glycoclusters for Multivalent Lectin-Carbohydrate Interactions: Influence of the Linker Arm
  • Rational Design and Synthesis of Optimized Glycoclusters for Multivalent Lectin-Carbohydrate Interactions: Influence of the Linker Arm (en)
skos:prefLabel
  • Rational Design and Synthesis of Optimized Glycoclusters for Multivalent Lectin-Carbohydrate Interactions: Influence of the Linker Arm
  • Rational Design and Synthesis of Optimized Glycoclusters for Multivalent Lectin-Carbohydrate Interactions: Influence of the Linker Arm (en)
skos:notation
  • RIV/00216224:14740/12:00061938!RIV13-MSM-14740___
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • P(ME08008), Z(MSM0021622413)
http://linked.open...iv/cisloPeriodika
  • 20
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
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  • 164147
http://linked.open...ai/riv/idVysledku
  • RIV/00216224:14740/12:00061938
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • carbohydrates; click chemistry; glycoclusters; lectin; multivalency (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • DE - Spolková republika Německo
http://linked.open...ontrolniKodProRIV
  • [0CE84FC88AAF]
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  • Chemistry - A European Journal
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  • 18
http://linked.open...iv/tvurceVysledku
  • Imberty, Anne
  • Wimmerová, Michaela
  • Cecioni, Samy
  • Praly, Jean-Pierre
  • Vidal, Sebastien
  • Matthews, Susan E
http://linked.open...ain/vavai/riv/wos
  • 000303497600019
http://linked.open...n/vavai/riv/zamer
issn
  • 0947-6539
number of pages
http://bibframe.org/vocab/doi
  • 10.1002/chem.201200010
http://localhost/t...ganizacniJednotka
  • 14740
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