About: Novel carbamoyl type quinine and quinidine based chiral anion exchangers implementing alkyne-azide cycloaddition immobilization chemistry     Goto   Sponge   NotDistinct   Permalink

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Description
  • The synthesis and chromatographic evaluation of a series of new Cinchona derived chiral weak anionexchangers is presented. Huisgen Cu(I) mediated alkyne-azide cycloaddition, so-called click chemistry,was used as an immobilization strategy. In this way it was possible to immobilize about 90% of offeredselector via 1,2,3-triazole linker, which displays a more efficient way of binding the selector to modifiedsilica compared to common radical mediated thiol-ene addition. Problems associated with potentialradical scavenging properties of chiral selectors thereby could be circumvented. The evaluation of thesynthesized chiral stationary phases regarding chromatographic behavior was carried out using polarorganic mode mobile phase composition and a set of representative chiral organic acids. Different loadingdensities revealed an optimum selector density of about 310 mol/g chiral stationary phase with respectto resolution and selectivity. A decrease of performance was observed for higher loading, indicatingmutual spatial influence of selector units leading to sterical hindrance. In addition, we observed thatthe effect of free azide groups on retention is negligible and the overall chromatographic behavior iscomparable to other Cinchona derived chiral stationary phases.
  • The synthesis and chromatographic evaluation of a series of new Cinchona derived chiral weak anionexchangers is presented. Huisgen Cu(I) mediated alkyne-azide cycloaddition, so-called click chemistry,was used as an immobilization strategy. In this way it was possible to immobilize about 90% of offeredselector via 1,2,3-triazole linker, which displays a more efficient way of binding the selector to modifiedsilica compared to common radical mediated thiol-ene addition. Problems associated with potentialradical scavenging properties of chiral selectors thereby could be circumvented. The evaluation of thesynthesized chiral stationary phases regarding chromatographic behavior was carried out using polarorganic mode mobile phase composition and a set of representative chiral organic acids. Different loadingdensities revealed an optimum selector density of about 310 mol/g chiral stationary phase with respectto resolution and selectivity. A decrease of performance was observed for higher loading, indicatingmutual spatial influence of selector units leading to sterical hindrance. In addition, we observed thatthe effect of free azide groups on retention is negligible and the overall chromatographic behavior iscomparable to other Cinchona derived chiral stationary phases. (en)
Title
  • Novel carbamoyl type quinine and quinidine based chiral anion exchangers implementing alkyne-azide cycloaddition immobilization chemistry
  • Novel carbamoyl type quinine and quinidine based chiral anion exchangers implementing alkyne-azide cycloaddition immobilization chemistry (en)
skos:prefLabel
  • Novel carbamoyl type quinine and quinidine based chiral anion exchangers implementing alkyne-azide cycloaddition immobilization chemistry
  • Novel carbamoyl type quinine and quinidine based chiral anion exchangers implementing alkyne-azide cycloaddition immobilization chemistry (en)
skos:notation
  • RIV/60461373:22310/14:43897209!RIV15-MSM-22310___
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • S
http://linked.open...iv/cisloPeriodika
  • 18.2.2014
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 33085
http://linked.open...ai/riv/idVysledku
  • RIV/60461373:22310/14:43897209
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • Liquid chromatography; Enantiomer separation; Copper-catalysis; Click chemistry; Cinchona alkaloids; Chiral anion exchange chromatography (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • NL - Nizozemsko
http://linked.open...ontrolniKodProRIV
  • [9340C4CE8399]
http://linked.open...i/riv/nazevZdroje
  • Journal of Chromatography A
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 1337
http://linked.open...iv/tvurceVysledku
  • Lindner, Wolfgang
  • Kohout, Michal
  • Hettegger, Hubert
  • Mimini, Vebi
http://linked.open...ain/vavai/riv/wos
  • 000334082200012
issn
  • 0021-9673
number of pages
http://bibframe.org/vocab/doi
  • 10.1016/j.chroma.2014.02.026
http://localhost/t...ganizacniJednotka
  • 22310
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