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Abstract: Two kinds of enantio-selective molecularly imprinted polymers (MIP) of N-tert-butoxycarbonyl-L-tryptophan (N-Boc-L-Trp) and N-tert-butoxycarbonyl-L-tyramine (N-Boc-L-Tyr), were synthesized by photo-induced and thermal-induced polymerization, respectively, in which acrylamide (functional monomer) and ethylene glycol dimethacrylate were co-polymerized in the presence of N-Boc-L-Trp and N-Boc-L-Tyr. Thermodynamic studies on chiral separation process using molecular imprinting were then carried out when the above two MIPs were employed as the stationary phase in liquid chromatography. Changes of entropy, enthalpy and Gibbs free energy in the process of imprinted-separation were analyzed. The results showed that not only the change of entropy played an important role in the separation, but also the solvation effect of the solutes and stationary phase, when a strong hydrogen-bond competitive solvent, such as isopropyl alcohol, alcohol or methanol, was supplemented into the mobile phase. Further studies showed that the molecular recognition of imprinted molecules and their enantiomorphs mainly depended on how well the geometric cavity structures of MIP suited the structure of the imprinted molecules
Template and target information: N-tert-butoxycarbonyl-L-tryptophan, N-Boc-L-Trp, N-tert-butoxycarbonyl-L-tyramine, N-Boc-L-Tyr
Author keywords: molecular imprinting polymer, thermodynamics, solvation, molecular recognition