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Analyte Templating: Enhancing the Enantioselectivity of Chiral Selectors upon Incorporation into Organic Polymer Environments


Type de document : Article de périodique
Langue : anglais

Responsabilité(s) secondaire (s) :



Editeur : American Chemical Society


Domaine (s) :


Mots clés :


Résumé anglais :

  • A simple strategy for preserving and enhancing the chiral recognition capacity of polymer-embedded chiral selectors is proposed, capitalizing on a temporary blockage of the receptor binding site with tightly binding analytes during the polymerization process. We demonstrate that the copolymerization of a quinine tert-butylcarbamate selector monomer with chiral (and achiral) 3,5-dichlorobenzoyl amino acids allows one to control to a certain extent the binding characteristics of the resultant polymeric chiral stationary phases. The structural and stereochemical requirements of the templating analytes for maximizing the chiral recognition capacity of the polymer-embedded selectors are probed. The chromatographic chiral recognition characteristics of the analyte-templated polymeric chiral stationary phases are analyzed with respect to binding capacities and affinities and compared to those obtained with a conventional silica-based surface-grafted reference material. Changes in substrate-specific enantioselectivity originating from analyte templating are also addressed.

Note : Extrait de "ANALYTICAL CHEMISTRY, Volume 77, Issue 15, 2005, Pages 5009-5018"


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