Analyte templating: enhancing the enantioselectivity of chiral selectors upon incorporation into organic polymer environments.
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.
Gavioli
Elena
E
Institute of Analytical Chemistry, University of Vienna, Währingerstrasse 38, A-1090 Vienna, Austria.
Maier
Norbert M
NM
Haupt
Karsten
K
Mosbach
Klaus
K
Lindner
Wolfgang
W
D008956:Models, Chemical; D015394:Molecular Structure; D009930:Organic Chemicals / Q000737:chemistry*; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D009930:Organic Chemicals; D011108:Polymers