(66d) Utilization of Peptoids in Membrane-Based Chiral Separations

Chirality is a common property of organic chemicals that has become an increasingly important aspect of chemical production, particularly in the production of pharmaceuticals, agrochemicals, and fragrances. Chiral compounds come in two versions, called enantiomers, which share most of the same physical properties, have identical NMR and IR spectrums, and react similarly in non-chiral systems. Currently techniques for separation of enantiomers include: crystallization, kinetic resolution, chromatographic separation, and membrane-based separations. The low material and operating costs make membrane-based separations a popular choice in industry. One disadvantage of membranes is that they become less enantioselective with multiple uses. Our research intends to increase selectivity by including peptoids in the membrane to add structural stability. Peptoids can be synthesized easily using an automated peptide synthesizer and can be created to arbitrary length with a large variety of side-chains. Properly substituted, they can form robust and stable helical structures which can be used to provide greater rigidity to the membrane. We are exploring the inclusion of peptoids within the polymer matrix in conjunction with the molecular imprinting technique often used in membrane-based chiral separations. This should be a relatively simple but effective way of increasing the long-term selectivity of membranes.