title: Construction and application of a stoichiometric displacement model for retention in chiral recognition of molecular imprinting.
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.
authors.affiliation: Department of Chemical Engineering, Institute of Biomechanical Engineering, Tsinghua University, Beijing 100084, PR China.
authors.forename: Ruifeng
authors.initials: R
authors.lastname: Sun
authors.forename: Huimin
authors.initials: H
authors.lastname: Yu
authors.forename: Hui
authors.initials: H
authors.lastname: Luo
authors.forename: Zhongyao
authors.initials: Z
authors.lastname: Shen
mesh_terms: D002851:Chromatography, High Pressure Liquid; D006860:Hydrogen Bonding; D008956:Models, Chemical; D011108:Polymers / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D011108:Polymers; D012997:Solvents