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Published on: August 18, 2017
Construction and application of a stoichiometric displacement model for retention in chiral recognition of molecular
Ruifeng Sun1, Huimin Yu, Hui Luo
1Department of Chemical Engineering, Institute of Biomechanical Engineering, Tsinghua University, Beijing 100084, PR China.
Abstract:
To do an extensive investigation of the chiral recognition mechanism of the molecular imprinting technique, two kinds of enantio-selective molecularly imprinted polymers (MIPs), 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, and were employed as the stationary phase in liquid chromatography. A stoichiometric displacement model for retention (SDM-R) was successfully constructed and applied to evaluate the chiral separation of the MIPs. The simulation results showed that the values of ln k' in the proposed SDM-R could be employed to characterize the efficiency of the MIP's total separation, and the value of n could be used to denote the space effect of the enantiomers interacting with the MIPs when the interaction between the solutes and MIPs was a hydrogen-bonding interaction. Further studies showed that the suitability of the MIP cavity structure mainly determined the chiral-recognition ability of the imprinting system, when a strong hydrogen-bond competitive solvent was added into the mobile phase.
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