L-phenylalanine Ethyl Ester Research Articles

Efficient separation of methyl ethyl ketone and water azeotrope using hydrophobic amino acid ester ionic liquids

BackgroundMethyl ethyl ketone (MEK), an essential organic solvent, is commonly produced via the n-butene method, where water emerges as the principal impurity. The conventional distillation processes, which are necessitated by the azeotropic behavior between MEK and water, result in a substantial expenditure of energy. As a result, liquid-liquid extraction represents a promising alternative for energy-efficient separation. MethodsIn this work, three hydrophobic amino acid ester ionic liquids L-phenylalanine ethyl ester bis(trifluoromethylsulfonyl) imide ([Phe][NTf2]), L-leucine ethyl ester bis(trifluoromethylsulfonyl) imide ([Leu][NTf2]) and L-valine ethyl ester bis(trifluoromethylsulfonyl) imide ([Val][NTf2]) were utilized as extractants for separation of the binary azeotrope methyl ethyl ketone and water. The effects of extraction time, extraction temperature, mass ratio of MEK-water mixture to ionic liquid and initial concentration of MEK on extraction efficiency were investigated. Significant findingsThe results demonstrate that the ionic liquid [Phe][NTf2] exhibits superior extraction ability for the separation of the azeotrope methyl ethyl ketone and water. The maximum extraction yield of 99.86 % was achieved with the optimum extraction conditions of extraction time, 10 min, extraction temperature, 293.15 K, mass ratio of mixture to ionic liquid, 1:1 and initial concentration of MEK, 20 %. In addition, the relationship between the structure of ionic liquids and their extraction performance was revealed by quantum chemical calculations of ionic liquids with MEK and water. These ionic liquids were positioned as promising environmentally friendly alternatives to traditional organic solvents for the recovery of MEK from aqueous solutions, providing valuable insights for industrial applications.

Construction of Tough Hydrogel Cross-Linked via Ionic Interaction by Protection Effect of Hydrophobic Domains.

Most hydrogels have poor mechanical properties, severely limiting their potential applications, and numerous approaches have been introduced to fabricate more robust and durable examples. However, these systems consist of nonbiodegradable polymers which limit their application in tissue engineering. Herein, we focus on the fabrication and investigate the influence of hydrophobic segments on ionic cross-linking properties for the construction of a tough, biodegradable hydrogel. A biodegradable, poly(γ-glutamic acid) polymer conjugated with a hydrophobic amino acid, l-phenylalanine ethyl ester (Phe), together with an ionic cross-linking group, alendronic acid (Aln) resulting in γ-PGA-Aln-Phe, was initially synthesized. Rheological assessments through time sweep oscillation testing revealed that the presence of hydrophobic domains accelerated gelation. Comparing gels with and without hydrophobic domains, the compressive strength of γ-PGA-Aln-Phe was found to be six times higher and exhibited longer stability properties in ethylenediaminetetraacetic acid solution, lasting for up to a month. Significantly, the contribution of the hydrophobic domains to the mechanical strength and stability of ionic cross-linking properties of the gel was found to be the dominant factor for the fabrication of a tough hydrogel. As a result, this study provides a new strategy for mechanical enhancement and preserves ionic cross-linked sites by the addition of hydrophobic domains. The development of tough, biodegradable hydrogels reported herein will open up new possibilities for applications in the field of biomaterials.

Emulsion-Based Gel Loaded with Ibuprofen and Its Derivatives.

The aim of this study was to evaluate the effect of vehicle and chemical modifications of the structure of active compounds on the skin permeation and accumulation of ibuprofen (IBU). As a result, semi-solid formulations in the form of an emulsion-based gel loaded with ibuprofen and its derivatives, such as sodium ibuprofenate (IBUNa) and L-phenylalanine ethyl ester ibuprofenate ([PheOEt][IBU]), were developed. The properties of the obtained formulations were examined, including density, refractive index, viscosity, and particle size distribution. The parameters of release and permeability through the pig skin of the active substances contained in the obtained semi-solid formulations were determined. The results indicate that an emulsion-based gel enhanced the skin penetration of IBU and its derivatives compared to two commercial preparations in the form of a gel and a cream. The average cumulative mass of IBU after a 24 h permeation test from an emulsion-based gel formulation through human skin was 1.6-4.0 times higher than for the commercial products. Ibuprofen derivatives were evaluated as chemical penetration enhancers. After 24 h of penetration, the cumulative mass was 1086.6 ± 245.8 for IBUNa and 948.6 ± 87.5 µg IBU/cm2 for [PheOEt][IBU], respectively. This study demonstrates the perspective of the transdermal emulsion-based gel vehicle in conjunction with the modification of the drug as a potentially faster drug delivery system.

Inhibitory Effect of Tanshinone IIA Nanomicelles on Tumor Growth and Angiogenesis in Mice with Cervical Carcinoma Transplantation

In recent years, traditional Chinese medicine (TCM), represented by tanshinone (Tas) and ganoderan polysaccharides, has attracted the attention of many scientists due to its mild effect of inhibiting tumors. In this research, poly-gamma-glutamic acid (γ-PGA) was degraded into small molecule γ-PGA fragments by high-temperature acidolysis, and L-phenylalanine ethylester (L-PAE) was combined with small molecule γ-PGA fragments to generate γ-PGA-LA by dehydration condensation. The material was mixed with fat-soluble Tas IIA to form PL-Tas IIA nanomicelles (NMs). In addition to physical characterization, the in vitro biological activity of the material was detected to establish a tumor-bearing nude mouse model, which was inoculated with cervical cancer HeLa cells. The nude mouse models were grouped, and the effect of NMs on the growth of transplanted tumors was observed by intraperitoneal injection. The results revealed that the nanoparticle size was approximately 139.6±3.8 nm, and it had a good EPR effect, which was conducive to passive targeted therapy of tumors. The polydispersity coefficient and zeta potential were 0.138±0.005 and 33.6±1.6 mV, respectively. The NM was cocultured with the cells under various concentration conditions, and the cell survival rate was more than 85%. The tumor cell uptake performance of the NM was ideal, and the cell uptake ratio reached 71.62% at 60 min, as determined by flow cytometry. An in vivo tumor test demonstrated that PL-Tas IIA had a favorite tumor inhibition effect. The tumor-bearing nude mouse model showed that the prepared NMs can inhibit tumor growth, induce angiogenesis of xenografts, and further induce tumor cell apoptosis, further verifying that the prepared NMs can inhibit cervical cancer tumor growth.

Separation and Purification of Kudinoside D and Its Nanoparticle Preparation and Characterization

Objective: To improve the water solubility of Kudinoside D. Methods: Using atmospheric column chromatography, semi-preparative high performance liquid chromatography and other means to separate and purify saponins from Ilex kudingcha C.J.Tseng, the compound Kudinoside D was obtained. Using polyglutamic acid (γ-PGA) and L-phenylalanine ethyl ester (L-PAE) as raw materials, Kudinoside D nanoparticles were prepared by precipitation method and dialysis method respectively. The physical and chemical properties of nanoparticles were characterized by transmission electron microscopy and dynamic nanoparticle size analyzer, and their in vitro drug release characteristics were investigated by dialysis. Results: Compared with the precipitation method, the encapsulation efficiency and drug loading of Kudinoside D nanoparticles prepared by the dialysis method were increased by 1.5 and 4.5 times, respectively, the encapsulation rate reached 65.46%, and the drug loading reached 13.24%. Kudinoside D nanoparticles had a regular spherical shape with an average particle size of (75±25) nm and a Zeta potential of 33.7. Conclusion: In vitro drug release experiments show that Kudinoside D nanoparticles can significantly improve the water solubility of the drug and have a good sustained release effect in vitro.

Synthesis of malonamide pseudopeptidic compounds using a pseudo five-component reaction and evaluation of their gelation properties

A new class of malonamide pseudopeptidic compounds (MPPCS) was prepared via an isocyanide-based pseudo five-component reaction. Amino acid esters, which were used in this reaction, were phenylalanine ethyl ester and glycine ethyl ester. MPPCS that were obtained from l-phenylalanine ethyl ester and glycine ethyl ester gave stable gels in the mixture of dimethyl sulfoxide (DMSO)/water as solvent while MPPCs derived from d-phenylalanine did not give gel. Also, when MPPCS of d- and l-form (1:1) were mixed, they could not create a gel in low and even high concentrations. The sol-gel phase transition temperature of the gels showed that they have agreeable thermal stability. Rheological results showed high mechanical strength for some of gels. Fourier transform infrared (FT-IR) spectra indicated that three types of driving forces have the key role in this self-assembly include hydrogen bondings, van der Waals, and π-π interactions. Moreover, morphology of the xerogel was clarified using the scanning electron microscope (SEM) image.

Preparation of PGA-PAE-Micelles for Enhanced Antitumor Efficacy of Cisplatin.

Poly-γ-l-glutamic acid (PGA) is an outstanding drug carrier candidate owning to its excellent biodegradability and biocompatibility. The PGA carrier may shield toxic drugs from the body and enable the delivery of poorly soluble or unstable drugs and thereby minimize the side effects and improve drug efficacy. However, the limitation of PGA as a drug carrier is low drug loading efficiency (DLE), which is usually below 30%. In this study, we reported a chemical modification method using l-phenylalanine ethyl ester (PAE). PGA-PAE construct was amphiphilic, which could form micelles in aqueous solution. Cisplatin (CDDP), a commonly used chemotherapy drug whose side effect is well-known, was used as a model molecule to test the drug-loading efficiency of PGA-PAE. In this paper, two sizes of CDDP-loaded PGA-PAE micelles (M(Pt)-1 and M(Pt)-2) were prepared, the average diameter of M(Pt)-1 was 106 ± 6 nm and M(Pt)-2 was 210 ± 9 nm. The DLE of M(Pt)-1 and M(Pt)-2 was 52.8 ± 2.2 and 55.8 ± 1.2%, respectively. Both exhibited excellent biocompatibility, stability, and drug-retaining capability in physiological condition. The in vitro accumulative drug-releasing profile, IC50 for different tumor cell lines HeLa, A549, and HCCC9810, and in vivo pharmacokinetics were similar between these two micelles; however, M(Pt)-1 showed higher tumor tissue retention and longer efficient cancer cell internalization time (up to 20 d). Our results suggested PGA-PAE micelle carriers reduced the toxicity of CDDP and its size at around 100 nm was the better for CDDP high-efficacy.

Characterization and analytical development for amphiphilic poly(γ-glutamic acid) as raw material of nanoparticle adjuvants

Amphiphilic graft copolymer consisting of poly(γ-glutamic acid) (γ-PGA) as the hydrophilic backbone and L-phenylalanine ethyl ester (Phe) as the hydrophobic side chain is an important biodegradable polymer with great potential in medical applications. In this research, we established analytical methods for the characterization and quality control of γ-PGA-graft-Phe (γ-PGA-Phe), which forms nanoparticles in aqueous solution, as a deployment platform in practical applications for vaccine adjuvants. The SEC-RI/MALS system, which uses size exclusion chromatography (SEC) coupled with a multi_angle light scattering (MALS) detector and refractive index (RI) detector, was developed to evaluate the characteristics of various types of polymers. By this method, it was indicated that absolute molecular weight (MW) should be used to measure the branch polymer. A gradient reversed phase HPLC (RP-HPLC) method was developed for the content of γ-PGA-Phe and the impurity levels to control product quality and safety. This quantitative approach could become key elements for identifying and characterizing γ-PGA-Phe. In addition, the degradation mechanism of γ-PGA-Phe was also identified as cleavage of main-chain of γ-PGA-Phe based on the stability study of γ-PGA-Phe in buffer solution with various pH values. The analytical developments described above will be important for use in both characterization and formulation design of biopolymers. Nanoparticles (NPs) composed of well-characterized biodegradable γ-PGA-Phe are expected to have a variety of potential clinical applications such as their use as drug and vaccine carriers.

Immobilization of helical poly(phenylacetylene)s having l-phenylalanine ethyl ester pendants onto silica gel as chiral stationary phases for HPLC

Novel one-handed helical copoly(phenylacetylene)s bearing a small amount of 3-(triethoxysilyl)propyl residues (CPAs 1–4) were synthesized, and efficiently chemically immobilized onto silica gel by the intermolecular polycondensation of the triethoxysilyl groups. Their chiral recognition abilities were evaluated as immobilized-type chiral stationary phases (CSPs) for high performance liquid chromatography (HPLC). These immobilized-type CSPs showed different chiral recognition abilities from the corresponding coated-type CSPs, which may be ascribed to the conformational change in the copoly(phenylacetylene)s during the immobilization process according to the diffuse reflectance circular dichroism (DRCD) measurement of the copolymer. In addition, the immobilized-type CSPs showed a universal solvent tolerability, for instance, CHCl3-containing eluents that cannot be used with the corresponding coated-type CSPs could now be used for the immobilized-type CSPs so that the chiral recognition of i-CSP-2 for the racemic 1-(9-anthyl)-2,2,2-trifluoroethanol (5) was improved with separation factors comparable or higher than those obtained on the popular polysaccharide-based CSPs. The intermolecular polycondensation of the triethoxysilyl groups of the copoly(phenylacetylene)s is a valuable immobilization method for poly(phenylacetylene)-based CSPs.

Synthesis and evaluation of l-phenylalanine ester-based chiral ionic liquids for GC stationary phase ability

Several l-phenylalanine alkyl ester-based cations formed ionic liquids after coupling with bis-(perfluoroethylsulfonyl) imide ([(C2F5SO2)2N]) and bis-(trifluoromethanesulfonyl) amide ([(CF3SO2)2N]). The relationship between the structure of l-phenylalanine alkyl ester cations and perfluorinated anions and properties of subsequently synthesized chiral ionic liquids was investigated. The ionic liquids were obtained in good yields and were liquid at room temperature. The ionic liquids having a methyl and ethyl substituent on the cation unit exhibited the highest thermal decomposition temperatures that ranged from 280°C to 296°C among the synthesized ionic liquids. These ionic liquids displayed the lowest glass transition temperatures of between −45°C to −51°C. The introduction of a different alkyl substituents on the cation caused the melting point and viscosity of the ionic liquids to vary slightly. Ionic liquids based on the [(C2F5SO2)2N] anion presented higher melting points than those based on the [(CF3SO2)2N] anion, for each corresponding cation. The neat chiral ionic liquids showed different fluorescence spectral behavior when excited at the same wavelength. Steady-state fluorescence spectroscopic measurements revealed the chiral discrimination of l-Phenylalanine ethyl ester bis-(perfluoroethylsulfonyl) imide for pure enantiomers of 2,2,2-trifluoroanthryl ethanol.

X-ray structures and spectroscopic properties of chiral thiosemicarbazides as studied by computational calculations

GRAPHICAL ABSTRACT

Fabrication of novel vesicles of triptolide for antirheumatoid activity with reduced toxicity in vitro and in vivo.

Triptolide (TP) displays a strong immunosuppression function in immune-mediated diseases, especially in the treatment of rheumatoid arthritis. However, in addition to its medical and health-related functions, TP also exhibits diverse pharmacological side effects, for instance, liver and kidney toxicity and myelosuppression. In order to reduce the side effects, a nano drug carrier system (γ-PGA-l-PAE-TP [PPT]), in which TP was loaded by a poly-γ-glutamic acid-grafted l-phenylalanine ethylester copolymer, was developed. PPT was characterized by photon scattering correlation spectroscopy and transmission electron microscopy, which demonstrated that the average diameter of the drug carrier system is 98±15 nm, the polydispersity index is 0.18, the zeta potential is −35 mV, and the TP encapsulation efficiency is 48.6% with a controlled release manner. The methylthiazolyldiphenyl-tetrazolium bromide assay and flow cytometry revealed that PPT could decrease toxicity and apoptosis induced by free TP on RAW264.7 cells, respectively. The detection of reactive oxygen species showed that PPT could decrease the cellular reactive oxygen species induced by TP. Compared with the free TP-treated group, PPT improved the survival rate of the mice (P<0.01) and had no side effects or toxic effects on the thymus index (P>0.05) and spleen index (P>0.05). The blood biochemical indexes revealed that PPT did not cause much damage to the kidney (blood urea nitrogen and creatinine), liver (serum alanine aminotransferase and aspartate aminotransferase), or blood cells (P>0.05). Meanwhile, hematoxylin and eosin staining and terminal-deoxynucleotidyl transferase dUTP nick-end labeling staining indicated that PPT reduced the damage of free TP on the liver, kidney, and spleen. Our results demonstrated that PPT reduced free TP toxicity in vitro and in vivo and that it is a promising fundamental drug delivery system for rheumatoid arthritis treatment.

Synthesis of Novel Chiral Sulfonamide‐Bearing 1,2,4‐Triazole‐3‐thione Analogs Derived fromD‐andL‐Phenylalanine Esters as Potential Anti‐Influenza Agents

Novel enantiopure 1,2,4-trizole-3-thiones containing a benzensulfonamide moiety were synthesized via multistep reaction sequence starting with D-phenylalanine methyl ester and L-phenylalanine ethyl ester as a source of chirality. The chemical structures of all compounds were characterized by elemental analysis, UV, IR, (1) H NMR, (13) C NMR, 2D NMR (HETCOR), and mass spectral data. All compounds were tested in vitro antiviral activity against a broad variety of DNA and RNA viruses and in vitro cytostatic activity against murine leukemia (L1210), human T-lymphocyte (CEM) and human cervix carcinoma (HeLa) cell lines. Although enantiopure 1,2,4-triazole-3-thione analogs in (R) configuration emerged as promising anti-influenza A H1N1 subtype in Madin Darby canine kidney cell cultures (MDCK), their enantiomers exhibited no activity. Especially compounds , , , , and (EC50 : 6.5, 6.1, 2.4, 1.6, 1.7μM, respectively) had excellent activity against influenza A H1N1 subtype compared to the reference drug ribavirin (EC50 : 8.0μM). Several compounds have been found to inhibit proliferation of L1210, CEM and HeLa cell cultures with IC50 in the 12-53μM range. Compound and in (R) configuration were the most active compounds (IC50 : 12-22μM for and IC50 : 19-23μM for ). Chirality 28:495-513, 2016. © 2016 Wiley Periodicals, Inc.

Room temperature stable ClPrNTf2 ionic liquid utilizing for chemical sensor development

A stable ionic liquid was prepared at room-temperature using the metathesis reaction, which was consummated by the reaction of l-Phenylalanine ethyl ester hydrochloride (chlorpromazine hydrochloride) with lithium-bis(trifluoromethane)sulfonamide in water (shortly, ClPrNTf2). The prepared ClPrNTf2 was characterized in details with various conventional methods. Here, a thin-layer of ClPrNTf2 onto glassy carbon electrode (GCE; Surface area: 0.0316 cm2) is deposited with conducting coating agents (5% nafion) to fabricate a selective and selective 3-methoxy phenol sensor in short response time in phosphate buffer solution. The fabricated phenolic chemical sensor is also exhibited higher sensitivity, large-dynamic concentration ranges, long-term stability, and improved electrochemical performances towards 3-methoxy phenol. The calibration plot is linear (r2 = 0.9836) over the large 3-methoxy phenol concentration ranges (0.09 nM to 0.9 mM). The sensitivity and detection limit is ∼2.3244 μAcm−2μM−1 and ∼0.022 ± 0.002 nM (signal-to-noise ratio, at a SNR of 3) respectively. This novel effort is initiated a well-organize way of efficient sensor improvement with ClPrNTf2 ionic liquid for toxic pollutants in environmental and health-care fields in large scales.

Polymer vesicles prepared from the (l-phenylalanine ethyl ester)-modified hyaluronic acid

In recent years, polymer vesicles prepared by self-assembly techniques have attracted increasing scientific interest because of their numerous extensive applications in drug release, nano-reactors and catalysis. In this work, hyaluronic acid (HA) was hydrophobically modified by l-phenylalanine ethyl ester (l-Phe) via amidation reaction between the carboxylic group of HA and the amine group of l-Phe. The amphiphilic polymers could self-assemble into nanoparticles of vesicle structure. The size and wall thickness of the vesicles were dependent on the modification degree of l-Phe. The results showed that with the increase of the modification degree of l-Phe, the size of the vesicles gradually decreased and the wall thickness of the vesicles gradually increased. Morphologies of the vesicles were characterized by transmission electron microscopy (TEM), scanning electron microscope (SEM) and atomic force microscope (AFM).

Amphiphilic γ-PGA nanoparticles administered on rat middle ear mucosa produce adjuvant-like immunostimulation in vivo

Conclusion: Amphiphilic biodegradable nanoparticles (NPs) composed of poly(γ-glutamic acid) conjugated with L-phenylalanine ethylester (γ-PGA-Phe NPs) applied on the rat middle ear mucosa produce an inflammatory type 1 response. The observation is of relevance for the use of γ-PGA-Phe NPs as a concomitant antigen delivery system and adjuvant measure in the context of vaccinations. Objectives: To examine effects of topical mucosal administration of γ-PGA-Phe NPs as a potentially combined antigen delivery system and adjuvant. Methods: γ-PGA-Phe NPs were administered on rat middle ear mucosa in a sham-controlled design and the response was monitored, focusing on soluble markers in mucosal surface liquids and on overall histopathology. Results: γ-PGA-Phe NPs produced a dose- and time-dependent inflammatory response characterized by generation of proinflammatory cytokines (IL-1α, IL-1β, IL-6, MIP-1α, and TNF-α) and associated histopathological changes.

Production of stable quinine nanodispersions using esterified γ-polyglutamic acid biopolymer

Novel methods are needed for the development of nanodispersed drug formulations to enhance bioavailability of many hydrophobic pharmaceuticals. The poorly water-soluble quinine is a well-known anti-malaria drug which can be used as a promising model compound for the development of novel nanodispersed formulations. In addition to hydrophobic drug's own affecting properties, surfactants play an important role for the enhancement of their low bioavailability by preparing stable dispersions. Amphiphilic compounds can efficiently be used to stabilize colloidal fragments by preventing the precipitation or crystallization of poorly water-soluble active ingredients during fabrication. A novel biopolymer derivative based on the biotechnologically produced γ-polyglutamic acid (γ-PGA) from Bacillus licheniformis cultivation was developed for encapsulation of the active ingredient. High-molecular γ-PGA is an anionic polyelectrolyte that was optimized and modified with hydrophobic l-phenylalanine ethyl ester (l-PAE) to form an amphiphilic comb polymer P(γ-GA-r-l-PAE) with surfactive properties. The approach of the nanodispersion polymer concentration, molecular weight and grafting degree enables the efficient stabilization of the poorly water-soluble model drug. The research presented in this report indicates the potential benefits of hydrophobically modified γ-PGA and suggests its potential role in forming stable dispersions for future pharmaceutical applications.

Synthesis of Novel Nucleoside Analogue Phosphorothioamidate Prodrugs and in vitro Anticancer Evaluation Against RKO Human Colon Carcinoma Cells

Novel phosphorothioamidates of pyrimidine nucleoside analogues have been prepared and evaluated in vitro against RKO human colon cancer cell by the MTT cytotoxicity assay. The parent nucleoside analogues were inactive in this assay, while the phosphorothioamidate prodrugs were active at low uM levels in some cases. The O-isopropyl phosphorothioamidate of 2 ′,3 ′-O-isopropylidene-uridine containing the L-phenylalanine ethyl ester 6f was the most active at 148 uM, a 10-fold enhancement in anticancer activity compared with the parent nucleoside 2 with no increase in cytotoxicity.

Investigation on thermoresponsive behavior of biodegradable poly(γ-glutamic acid)-graft-L-phenylalanine ethyl ester

The thermosensitivity of biodegradable and non-toxic amphiphilic polymer derived from a naturally occurring polypeptide and a derivative of amino acid was first reported. The amphiphilic polymer consisted of poly(γ-glutamic acid) (γ-PGA) as a hydrophilic backbone, and L-phenylalanine ethyl ester (L-PAE) as a hydrophobic branch. Poly(γ-glutamic acid)-graft-L-phenylalanine (γ-PGA-graft-L-PAE) with grafting degrees of 7–49% were prepared by varying the content of a water-soluble carbodiimide (WSC). γ-PGA-graft-L-PAE with a grafting degree of 49% exhibited thermoresponsive phase transition behavior in an aqueous solution at around 80°C. The copolymers with grafting degrees in the range of 30–49% showed thermoresponsive properties in NaCl solution. A clouding temperature (Tcloud) could be adjusted by changing the polymer concentration and/or NaCl concentration. The thermoresponsive behavior was reversible. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

Study on the Weakest Interaction Model for Chiral Resolution Using Molecularly Imprinted Polymer

Molecularly imprinted polymers (MIPs) of L-phenylalanine ethyl ester were synthesized in this study. Then, the prepared MIPs were packed in a stainless column and evaluated as the chiral stationary phases of high performance liquid chromatography (HPLC). The MIPs exhibited a considerable capability of chiral separation between template molecule and its enantiomer with the separation factor of 1.69. Furthermore, the weakest interaction model was introduced to study the chiral recognition mechanism of MIPs. The results suggested that the weakest interaction between the template molecule and the imprinted cavity played crucial role in chiral separation, and the molecular tension should be taken into consideration during the separation procedure. The separation factor of 2.07 was calculated by the theoretical model, which was very close to the value obtained from chromatographic experiment.