CN108864364B - Preparation method of L-phenylalanine molecularly imprinted polymer - Google Patents
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Abstract
The invention discloses a preparation method of a novel L-phenylalanine molecularly imprinted polymer, which takes imidazole type ionic liquid containing double bonds and amino functional groups as a functional monomer and L-phenylalanine as a template molecule, and prepares the novel L-phenylalanine molecularly imprinted polymer through the synergistic effect of multiple sites such as hydrogen bonds, pi-pi conjugation, electrostatic force and the like between the imidazole type ionic liquid and the L-phenylalanine. The prepared molecularly imprinted polymer has higher selectivity on L-phenylalanine in a water phase, and can realize chiral resolution of racemic DL-phenylalanine. The ionic liquid with multiple functional groups is used as a functional monomer, and the application range of the molecular imprinting functional monomer selection is widened.
Description
Technical Field
The invention belongs to the technical field of molecular imprinting, and relates to a preparation method of an L-phenylalanine molecular imprinting polymer.
Background
Chiral substances are ubiquitous in nature, phenylalanine is no exception, and it exists in two enantiomers: l-phenylalanine (L-Phe) and D-phenylalanine (D-Phe). Wherein, L-Phe is an important medical and edible chemical intermediate, is one of eight essential amino acids required by human body, but the human body can not synthesize the L-Phe and can only be obtained by external intake, so the L-Phe has high application value. D-Phe has distinct physiological properties and pharmaceutical activities from it.
The L-phenylalanine can be prepared by a biological method, a chemical synthesis method and the like, the biological method can synthesize relatively pure L-phenylalanine, the product specificity is relatively strong, but the method has the defects of low fermentation concentration, long production period, low yield and the like. The chemical principle can obtain higher production efficiency by using more starting materials, but the product is mainly DL-phenylalanine, and a single enantiomer L-Phe or D-Phe can be obtained by chiral resolution. At present, methods for resolving an amino acid enantiomer mainly comprise a crystallization method, an enzymatic method, a chemical resolution method, a membrane separation method, a chromatography method and the like, but generally the production process is complex, the requirement on environmental conditions is high, and the cost is high, so that the exploration of a method for resolving an amino acid enantiomer with good identification selectivity, low cost and simple operation is imperative, and the method has very important significance in the fields of life science, fine chemistry, pharmaceutical chemistry, material chemistry and the like.
In recent years, molecular imprinting techniques have been studied and applied to the separation of chiral compounds, providing a novel and efficient approach to the resolution of chiral enantiomers. However, the molecular imprinting technology at the present stage has some difficult problems, such as the preparation of the molecular imprinting polymer in the aqueous phase and the recognition in the aqueous phase can not be well realized, and the application of the molecular imprinting polymer in many aspects is limited.
The ionic liquid has the advantages of designability of structure, better thermal stability, low vapor pressure, good dissolving capacity and the like, is widely applied to the fields of catalysis science, electrochemistry, material science, environmental science, separation technology and the like, and shows good application prospect. The research of using ionic liquid as functional monomer for preparing molecular imprinted polymer is a new subject developed in recent years, and in 2010 luxu biao et al (chinese patent CN200910115863.2), caffeine and theophylline molecular imprinted polymer capable of being effectively imprinted and separated in aqueous phase is successfully prepared by using any one of ionic liquid of brominated 1- (alpha-methacrylic acid) -3-methylimidazole, brominated 1- (alpha-methacrylic acid) -3-ethylimidazole, brominated 1- (crotonic acid) -3-methylimidazole and brominated 1- (crotonic acid) -3-ethylimidazole as functional monomer; 2011 Guo Lu et al uses 1-vinyl-3-butyl imidazole ionic liquid as functional monomer to prepare chlorsulfuron molecularly imprinted polymer; 2011 Luxu Biao synthesizes a novel molecularly imprinted polymer by using brominated 1- (alpha-methacrylic acid) -3-methylimidazole as a functional monomer for detecting or separating water-soluble acid dye in wastewater and beverage; in 2013, Van Jie Ping takes any one of brominated 1-carboxymethyl-3-vinyl imidazole ionic liquid, brominated 1-carboxyethyl-3-vinyl imidazole ionic liquid, brominated 1-carboxybutyl-3-vinyl imidazole ionic liquid and brominated 1-carboxypentyl-3-vinyl imidazole ionic liquid as a functional monomer to synthesize an epinephrine molecularly imprinted polymer, and the common point of the two is that the ionic liquid and a template molecule have multiple action sites, so that the defect that the traditional monomer only uses single hydrogen bond action to prepare the molecularly imprinted polymer is overcome, and the imprinted polymer prepared by taking the ionic liquid as the functional monomer can interact with the template molecule in a water phase through various action modes such as pi-pi conjugation, hydrogen bond, electrostatic force and the like, so that the epinephrine molecularly imprinted polymer has high adsorption performance and selectivity, can be used for separating molecules such as amino acid, protein, medicine, etc. in water phase.
Disclosure of Invention
The invention aims to provide a preparation method of an L-phenylalanine molecularly imprinted polymer, and the obtained imprinted polymer has high identification on target molecules in a water phase and has an excellent resolution effect on racemic DL-phenylalanine.
The invention is realized by the following technical scheme:
a preparation method of an L-phenylalanine molecularly imprinted polymer comprises the following operations:
1) dissolving template molecule L-phenylalanine and functional monomer chlorinated 1-vinyl-3-carbamoylmethylimidazole ionic liquid in a water-organic phase mixed solvent, and performing prepolymerization for 10-12 h at 4-8 ℃; wherein the molar ratio of the L-phenylalanine to the chlorinated 1-vinyl-3-carbamoylmethylimidazole is 1: 4-6;
2) placing a dispersant polyvinylpyrrolidone into the pre-polymerized mixed solution, heating and stirring until the polyvinylpyrrolidone is completely dissolved, wherein the addition amount of the polyvinylpyrrolidone is 10-20% of the mass of the functional monomer;
3) dissolving a crosslinking agent ethylene glycol dimethacrylate and an initiator azobisisobutyronitrile into the mixed solution in sequence, and uniformly stirring, wherein the molar ratio of L-phenylalanine to chlorinated 1-vinyl-3-carbamoylmethylimidazole to ethylene glycol dimethacrylate is 1 (4-6) to (15-16);
4) ultrasonically degassing the mixed solution obtained in the step 3), introducing nitrogen for 10-15 min, rapidly sealing the mixed solution, heating to 55-80 ℃, reacting for 12-24 h under stirring to obtain polymer particles, and sequentially washing with distilled water and ethanol for multiple times;
5) eluting the L-phenylalanine from the washed polymer particles, washing with distilled water again, and drying in vacuum to obtain the L-phenylalanine molecularly imprinted polymer.
The water-organic phase mixed solvent is a water-methanol mixed solvent or a water-ethanol mixed solvent, wherein the volume ratio of water to methanol or ethanol is 1: 2-3.
The addition amount of the azodiisobutyronitrile is 10-20% of the mass of the functional monomer.
The reaction in the step 4) is carried out by heating to 60-65 ℃ and keeping the temperature at 400-450 r.min-1Reacting for 20-24 hours under stirring, and obtaining white polymer particles after the reaction is finished.
The operation of eluting the L-phenylalanine comprises the following steps:
subjecting the polymer particles to ultrasonic degassing with 0.5-0.6 mol/L NaCl solution at 20-25 deg.C for 10min, and subjecting to ultrasonic degassing at 25 deg.C for 120 r/min-1Shaking for 24h at a rotating speed to elute the L-phenylalanine;
then at 8500r min-1Centrifuging for ten minutes at the rotating speed, taking the supernatant, detecting the L-phenylalanine at 257.5nm by using an ultraviolet-visible spectrophotometer, and if the absorbance is more than 0.001, continuously eluting the polymer particles with the L-phenylalanine until the absorbance of the L-phenylalanine is detected to be less than 0.001.
The vacuum drying is carried out for 24 hours at the temperature of 50-60 ℃.
The maximum imprinting factor alpha of the prepared L-phenylalanine molecularly imprinted polymer is 2.23-3.86, and the selection factor beta is 1.28-2.12.
Compared with the prior art, the invention has the following beneficial technical effects:
the invention provides a preparation method of an L-phenylalanine molecularly imprinted polymer, which is a method for preparing a novel L-phenylalanine molecularly imprinted polymer by taking imidazole type ionic liquid (chlorinated 1-vinyl-3-carbamoylmethylimidazole ionic liquid) with double bonds and amino functional groups as a functional monomer and L-phenylalanine as a template molecule through the coordination of multiple sites such as hydrogen bonds, pi-pi conjugation, electrostatic force and the like of the template molecule and the functional monomer. The prepared polymer is used for adsorbing and separating L-phenylalanine in a water phase through multi-site synergistic effect, has the advantages of high adsorption quantity, good selectivity and good chiral resolution effect, and widens the application range of the molecular imprinting technology.
The preparation method of the L-phenylalanine molecularly imprinted polymer provided by the invention has the advantages of simple method, uniform product and low requirement on environment, the obtained imprinted polymer can realize high identification on target molecules through multi-site synergistic action in a water phase, has excellent resolution effect on racemic DL-phenylalanine, and widens the application of the molecularly imprinted polymer in the fields of biology, medicine, life science and the like.
Detailed Description
The present invention will now be described in further detail with reference to specific examples, which are intended to be illustrative, but not limiting, of the invention.
The preparation method of the L-phenylalanine molecularly imprinted polymer provided by the invention comprises the following operations:
1) dissolving template molecule L-phenylalanine and functional monomer chlorinated 1-vinyl-3-carbamoylmethylimidazole ionic liquid in a water-organic phase mixed solvent, and pre-polymerizing for 10-12 h in a refrigerator at the temperature of 4 ℃; wherein the molar ratio of the L-phenylalanine to the chlorinated 1-vinyl-3-carbamoylmethylimidazole is 1: 4-6;
2) placing a dispersant polyvinylpyrrolidone into the pre-polymerized mixed solution, heating and stirring until the polyvinylpyrrolidone is completely dissolved, wherein the addition amount of the polyvinylpyrrolidone is 10-20% of the mass of the functional monomer;
3) dissolving a crosslinking agent ethylene glycol dimethacrylate and an initiator azobisisobutyronitrile into the mixed solution in sequence, and uniformly stirring, wherein the molar ratio of L-phenylalanine to chlorinated 1-vinyl-3-carbamoylmethylimidazole to ethylene glycol dimethacrylate is 1 (4-6) to (15-16);
4) ultrasonically degassing the mixed solution obtained in the step 3) for 5min at the constant temperature of 25 ℃, then introducing nitrogen for 10-15 min, quickly sealing the mixed solution, heating to 55-80 ℃, reacting for 12-24 h under stirring to obtain polymer particles, and sequentially washing with distilled water and ethanol for multiple times respectively;
5) eluting the L-phenylalanine from the washed polymer particles, washing with distilled water again, and drying in vacuum to obtain the L-phenylalanine molecularly imprinted polymer.
Wherein the structural formula of the chlorinated 1-vinyl-3-carbamoylmethylimidazole is as follows:
specific examples are given below.
Example 1
Weighing 66 mgL-phenylalanine, 299mg chloridized 1-vinyl-3-carbamyl methyl imidazole ionic liquid and dissolving in 60mL water-ethanol (V)Water (W):VEthanolPre-polymerizing for 12h in a refrigerator at 4 ℃ in a mixed solvent of 1:3), adding 30mg of polyvinylpyrrolidone (PVP), heating and stirring until the PVP is completely dissolved;
sequentially adding 1.2ml of EGDMA and 45mg of AIBN, stirring, ultrasonic degassing at 25 deg.C for 5min, introducing nitrogen, sealing for 15min, and sealing at 450 r.min-1Under the stirring action, carrying out hot polymerization in water bath at 65 ℃ for 24 hours to obtain white polymer particles;
washing with distilled water and ethanol 100mL respectively for 3 times, ultrasonically eluting with 200mL 0.6mol/L NaCl solution for 10min, and performing ultrasonic elution at 25 deg.C for 120r min-1Shaking for 24h at a rotating speed to elute the L-phenylalanine;
at 8500 r.min-1Centrifuging for ten minutes at the rotating speed, taking the supernatant, detecting the L-phenylalanine at 257.5nm by using an ultraviolet-visible spectrophotometer, and if the absorbance is more than 0.001, eluting the centrifuged particles again according to the same steps until the absorbance of the L-phenylalanine in the eluent is less than 0.001.
And washing the eluted polymer with 300mL of distilled water for 3 times, and drying in vacuum at 50 ℃ for 24h to obtain the L-phenylalanine molecularly imprinted polymer (L-MIP).
Synthesis of non-imprinted polymer (L-NIP) the procedure was as above except that the template molecule (L-Phe) was not added.
The maximum imprinting factor of the molecularly imprinted polymer of L-phenylalanine prepared in this example was α ═ Q as determined by spectrophotometryL-MIP/QL-NIP3.86, the selection factor β ═ QL-MIP/QL-MIP-D＝2.12，(QL-MIPIs the adsorption capacity of the L-phenylalanine molecularly imprinted polymer to the L-phenylalanine, QL-NIPIs the adsorption capacity of the non-imprinted polymer to L-phenylalanine, QL-MIP-DIs the adsorption quantity of the L-phenylalanine molecularly imprinted polymer to the D-phenylalanine).
Example 2
Weighing 66mg of L-phenylalanine, 374mg of chlorinated 1-vinyl-3-carbamoylmethylimidazole ionic liquid and dissolving in 60mL of water-ethanol (V)Water (W):VEthanolPre-polymerizing for 12h in a refrigerator at 4 ℃ in a mixed solvent of 1:2), adding 37.6mg of polyvinylpyrrolidone (PVP), and heating and stirring until the PVP is completely dissolved;
sequentially adding 1.2ml of EGDMA and 48mg of AIBN, stirring, ultrasonic degassing at 25 deg.C for 5min, introducing nitrogen for 15min, rapidly sealing, and sealing at 450r min-1Under the stirring action, carrying out hot polymerization in water bath at 65 ℃ for 24 hours to obtain white solid particles;
washing with distilled water and ethanol 100mL respectively for 3 times, ultrasonically eluting with 200mL 0.6mol/L NaCl solution for 10min, and performing ultrasonic elution at 25 deg.C for 120r min-1Shaking for 24h at a rotating speed to elute the L-phenylalanine;
at 8500 r.min-1Centrifuging for ten minutes at the rotating speed, taking the supernatant, detecting the L-phenylalanine at 257.5nm by using an ultraviolet-visible spectrophotometer, and if the absorbance is more than 0.001, eluting the centrifuged particles again according to the same steps until the absorbance of the L-phenylalanine in the eluent is less than 0.001. The eluted polymer was washed with 300mL of distilled water 3 each timeAnd then, drying the mixture for 24 hours in vacuum at the temperature of 50 ℃ to obtain the L-phenylalanine molecularly imprinted polymer (L-MIP).
Synthesis of non-imprinted polymer (L-NIP) the procedure was as above except that the template molecule (L-Phe) was not added.
The maximum imprinting factor of the molecularly imprinted polymer of L-phenylalanine prepared in this example was α ═ Q as determined by spectrophotometryL-MIP/QL-NIP2.93, the selection factor β ═ QL-MIP/QL-MIP-D＝1.31。
Example 3
Weighing 66 mgL-phenylalanine, 448mg chloridized 1-vinyl-3-carbamoylmethylimidazole ionic liquid and dissolving in 60mL of water-ethanol (V)Water (W):VEthanolPre-polymerizing for 12h in a refrigerator at 4 ℃ in a mixed solvent of 1:3), adding 45mg of polyvinylpyrrolidone (PVP), heating and stirring until the PVP is completely dissolved;
sequentially adding 1.2mL of EGDMA and 50mg of AIBN, stirring, ultrasonic degassing at 25 deg.C for 5min, introducing nitrogen for 15min, rapidly sealing at 450 r.min-1Under the stirring action, carrying out hot polymerization in water bath at 65 ℃ for 24 hours to obtain white solid particles;
washing with distilled water and ethanol 100mL respectively for 3 times, ultrasonically eluting with 200mL 0.6mol/L NaCl solution for 10min, and performing ultrasonic elution at 25 deg.C for 120r min-1Shaking for 24h at a rotating speed to elute the L-phenylalanine;
at 8500 r.min-1Centrifuging for ten minutes at the rotating speed, taking the supernatant, detecting the L-phenylalanine at 257.5nm by using an ultraviolet-visible spectrophotometer, and if the absorbance is more than 0.001, eluting the centrifuged particles again according to the same steps until the absorbance of the L-phenylalanine in the eluent is less than 0.001. And washing the eluted polymer with 300mL of distilled water for 3 times, and drying in vacuum at 50 ℃ for 24h to obtain the L-phenylalanine molecularly imprinted polymer (L-MIP).
Synthesis of non-imprinted polymer (L-NIP) the procedure was as above except that the template molecule (L-Phe) was not added.
The molecularly imprinted polymer of L-phenylalanine prepared in this example was detected by spectrophotometryThe maximum imprinting factor is alpha-QL-MIP/QL-NIP2.23, the selection factor β ═ QL-MIP/QD-MIP＝1.28。
The embodiments given above are preferable examples for implementing the present invention, and the present invention is not limited to the above-described embodiments.
Claims (1)
1. A preparation method of an L-phenylalanine molecularly imprinted polymer is characterized by comprising the following operations:
weighing 66 mgL-phenylalanine, 299mg chloridized 1-vinyl-3-carbamyl methyl imidazole ionic liquid and dissolving in 60mL of water-ethanol mixed solvent, wherein V is in the water-ethanol mixed solventWater (W):VEthanolPre-polymerizing at 4 deg.c for 12 hr, adding vinyl pyrrolidone in 30mg, heating and stirring to dissolve completely;
sequentially adding 1.2ml of EGDMA and 45mg of AIBN, stirring, ultrasonic degassing at 25 deg.C for 5min, introducing nitrogen, sealing for 15min, and sealing at 450 r.min-1Under the stirring action, carrying out hot polymerization in water bath at 65 ℃ for 24 hours to obtain white polymer particles;
washing with distilled water and ethanol 100mL respectively for 3 times, ultrasonically eluting with 200mL 0.6mol/L NaCl solution for 10min, and performing ultrasonic elution at 25 deg.C for 120r min-1Shaking for 24h at a rotating speed to elute the L-phenylalanine;
at 8500 r.min-1Centrifuging for ten minutes at the rotating speed, taking the supernatant, detecting the L-phenylalanine at 257.5nm by using an ultraviolet-visible spectrophotometer, and if the absorbance is more than 0.001, eluting the centrifuged particles again according to the same steps until the absorbance of the L-phenylalanine in the eluent is less than 0.001.
And washing the eluted polymer with 300mL of distilled water for 3 times, and performing vacuum drying at 50 ℃ for 24 hours to obtain the L-phenylalanine molecularly imprinted polymer.
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| "The performance optimization and specific adsorption of L-phenylalanine imprinted polymers using 1-vinyl-3-carboxymethylimidazolium chloride as functional monomer";Bo Gao et al.;《Designed Monomers and Polymers》;20141218;第2.4.1节，Scheme 1，Table2，第3.7节 * |
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