Tailored polymer-supported templates in dynamic combinatorial libraries: simultaneous selection, amplification and isolation of synthetic receptors

P. Besenius, P.A.G. Cormack, J.Y. Liu, S.R. Otto, J.K.M. Sanders, D.C. Sherrington, Royal Society (Funder), EPSRC (Funder)

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The thermodynamically controlled synthesis and isolation of macrocyclic receptors from dynamic combinatorial libraries has been achieved in a single step using a polymer-supported template. The templates were cinchona alkaloids which show interesting enantio- and diastereoselective molecular recognition events in libraries based on pseudo-dipeptide building blocks. The synthetic routes used to derivatise the alkaloids and attach them to polymer supports minimised any influence of the tethering linkage on the templating activity. Systematic studies have been carried out to probe how the polymer morphology and the template loading affect the selectivity and isolation yield of the macrocyclic receptors. Molecular recognition between solid-phase bound templates and selected receptors also enabled their affinity-type chromatographic separation.
Original languageEnglish
Pages (from-to)9006-9019
Number of pages13
JournalChemistry - A European Journal
Volume14
Issue number29
DOIs
Publication statusPublished - 2008

Keywords

  • affinity chromatography
  • dynamic combinatorial chemistry
  • molecular recognition
  • polymer-supported templates
  • synthetic receptors

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