Novel membrane materials having EEE derivatives as a chiral recognition site

Molecularly imprinted polymeric membranes with tripeptide residue H–Glu(OBzl)–Glu(OBzl)–Glu(OBzl)–CH2– (EEE) were prepared during the membrane preparation process in the presence of a print molecule. The Boc–l-Trp imprinted polymeric membranes thus obtained showed adsorption selectivity toward the print molecule analogue, Ac–l-Trp. From the adsorption isotherms of Ac–Trp’s, the chiral recognition site, which was formed by the print molecule in the membrane preparation process, exclusively recognizes Ac–l-Trp, and the opposite isomer, Ac–d-Trp, is rejected. Enantioselective electrodialysis was attained and the separation factor toward l-isomer reached 5.0, reflecting adsorption selectivity. The membrane performance, such as the amount of enantiomer recognized and flux value of enantioselective electrodialysis, are greatly dependent on the concentration of tripeptide residues in the membrane.