Molecular imprinting of amino acid derivatives in macroporous polymers : Demonstration of substrate- and enantio-selectivity by chromatographic resolution of racemic mixtures of amino acid derivatives

Abstract

Substrate-selective macroporous polymers were prepared by a non-covalent imprinting procedure. By this method, acrylic polymers selective for d or l-phenylalanine ethyl esters were prepared utilizing coulombic interactions, during polymerization, between the print molecule ( d or l-phenylalanine ethyl ester) and the carboxyl group carried by the vinyl monomers. These polymers, after removal of print molecules, were used in a chromatographic procedure to examine their enatio- and substrate-selectivity for some amino acid derivatives. The best separation factor, α, for d, l-phenylalanine ethyl ester was found to be 1.30. The selectivity persisted to several months after intermittent applications.