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Reference type: Journal
Authors: Torres JJ, Gsponer N, Ramírez CL, Vera DM, Montejano HA, Chesta CA
Article Title: Experimental and theoretical studies on the enantioselectivity of molecularly imprinted polymers prepared with a chiral functional monomer.
Publication date: 2012
Journal: Journal of Chromatography A
Volume: 1266
Page numbers: 24-33.
DOI: 10.1016/j.chroma.2012.09.042
Alternative URL: http://www.sciencedirect.com/science/article/pii/S0021967312014409

Abstract: A comprehensive study on the enantioseparation of racemic bis[1-phenylethyl]amine (PEA) on a series of molecularly imprinted polymers (MIPs) prepared using the chiral functional monomer (S)-2-(2-methyl-acryloylamino)-3-phenyl propionic acid (MAPP) is reported. MIP-R, MIP-S and MIP-RS, were synthesized separately by imprinting the pure enantiomers (R-, S-PEA) and racemic PEA, respectively, MAPP, EDGMA as crosslinker and chloroform as the porogen. It was found that all MIPs prepared were able to resolve the PEA racemate. Residence times (tr) and enantioselectivity factors (α) were estimated from typical elution chromatography experiments. Frontal chromatography experiments were conducted to acquire the adsorption isotherms for both enantiomers on the different MIPs (and on the non-imprinted polymer, NIP). The adsorption isotherms were analyzed using the affinity spectrum (AS) and the expectation-maximization (EM) methods. The study also involved the theoretical evaluation of the MAPP/enantiomers interactions in the pre-polymer mixture. The EM method predicts mono- and bimodal distribution of affinity binding sites depending upon the polymer analyzed. Apparently, the enantioseparation process depends on relatively small differences in the stabilization of the diasteroisomeric ion-pairs PEA/MAPP complexes on the surface of the polymers
Template and target information: bis[1-phenylethyl]amine, PEA
Author keywords: Molecularly imprinted polymers, adsorption isotherms, HPLC, Binding site's distribution, racemic resolution

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