CN102225989B - Preparation method of new material for separating chiral aspartic acid - Google Patents
Preparation method of new material for separating chiral aspartic acid Download PDFInfo
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Abstract
The invention discloses a preparation method of a new material for separating chiral aspartic acid, and solves the problems of difficulty and low efficiency of L-Asp separation currently. The method comprises the following steps of: activation of silica gel particles; chemical bonding of the silica gel particles with a double bond-containing silane coupling agent; chemical grafting of the silica gel particles with polydimethylaminoethyl methacrylate; and preparation of silica gel particle surface molecularly imprinted polymer. The invention adopts silica gel particles as carriers, adopts dimethylaminoethyl methacrylate as a functional macromolecular material grafted on the particles or the particle surfaces, and adopts ether dihalide as a cross-linking agent to prepare the surface imprinted material with high molecular binding speed, strong recognition selectivity, high binding capacity to L-Asp; the surface imprinted material prepared by the invention is suitable for the requirements of industrial production, and has high material utilization rate, low cost, and very good selectivity, recognition and bonding performance to L-Asp molecules.
Description
Technical field
The present invention relates to the preparation method of the novel material of resolving chiral aspartic acid.
Background technology
Amino acid is the elementary cell of constitutive protein matter at the nature ubiquity, and is present in the intravital free state amino acid of life and in the metabolism of body and function are regulated, is also bringing into play very important effect.The natural amino acid of biologically active is the L-type; The amino acid of chemosynthesis preparation then is generally the racemic modification of DL-type; The physiological action of these two amino acid enantiomers is far different, and their biological activity and biological intravital chiral environment (enzyme, hormone, acceptor, antibody etc.) are closely related.
The fractionation of amino acid enantiomer has crucial meaning in the research of life science; Simultaneously; Along with the fast development of using in the fields such as amino acid is synthetic at medicine, food and fodder industry, daily chemicals; Amino acid to chemosynthesis carries out chiral separation, prepares optically pure amino acid and seems more and more important.
At present, the method for amino acid separation enantiomorph mainly contains crystallization process (classical approach), enzyme process, chemical resolution method, membrane separation process and chromatography (comprising gc (GC), performance liquid chromatography (HPLC), capillary electrophoresis (CE) method and chirality aglucon exchange chromatography methods such as (CLCE)).Above-mentioned several kinds of non-chromatographic processes, the narrow application range that has; The step that has is various, processing efficiency is low; The then cost that has is high, and the amplification process cost is expensive; And various chromatographys, but all be confined to the analytical chemistry field, be difficult to reach the suitability for industrialized production scale.Therefore, aspect the fractionation of amino acid enantiomer, have still that cost is high, separating effect is looked into and be difficult to reach problem such as mass-producing separation.
Molecularly imprinted polymer (Molecular Imprinted Polymer; One type of functional polymer material of MIPs) being tailored meticulously; Its inside is distributed with the trace hole of a large amount of template molecules; These trace holes and template molecule are complementary at aspects such as size, space structure, binding sites to heavens, make molecularly imprinted polymer have special identification selection property and good binding affinity to template molecule, are called artificial antibody or artificial susceptor by people.At present; Molecularly imprinted polymer has been widely used in various high-tech areas; Especially separation, purifying and the enrichment at material concentrates the field, is that the molecular engram solid phase extraction method (MIPSPE) of solid adsorbent is arisen at the historic moment with the molecularly imprinted polymer, obtained using widely.
Fractionation field at chiral amino acid; Though molecularly imprinted polymer has also received very big concern; Existing several studies, but have two significantly limitations in this respect: the method that (1) prepares imprinted polymer is entrapping method, the poor-performing of prepared imprinted polymer mostly; (2) imprinted polymer only is used as the chromatographic stationary phase at present mostly, is used for studying the compartment analysis of amino acid enantiomer, and its performance also far can not reach the level of solid extracting agent, can't realize amino acid enantiomer is carried out the SPE of mass-producing.
Summary of the invention
The fractionation efficient that the objective of the invention is to solve chiral amino acid is low, and is difficult to reach the problem of suitability for industrialized production scale, and a kind of preparation method of novel material of resolving chiral aspartic acid is provided.
The present invention utilizes surface grafting that the function grafting particulate PDMAEMAS/SiO of polydimethyl amino methyl ethyl propenoate (DMAEMA) is arranged
2And strong static and interaction of hydrogen bond between the acidic amino acid molecule adopt novel surface trace method, have implemented the molecular imprinting of enantiomorph L-aspartic acid (L-Asp), have made imprinted material MIP-PDMAEMA/SiO
2, for contrasting, furtherd investigate imprinted material MIP-PDMAEMA/SiO with D-aspartic acid (D-Asp)
2Molecular recognition characteristic to template molecule L-Asp.
The present invention realizes through following technical scheme:
A kind of preparation method of novel material of resolving chiral aspartic acid may further comprise the steps:
(1), silica gel surface chemical modification: the 10-15g activated silica gel is joined in the 100-150ml water solvent; And coupling agent γ-(methacryloxypropyl) propyl trimethoxy silicane of adding 10-15ml; React 20-24h down at 50 ℃; Product behind the suction filtration is used the ethanol repetitive scrubbing, and vacuum-drying makes the aerosil particles MPS-SiO through surface-treated
2
(2), silica particle surface chemical graft polymethyl acrylic acid: the aerosil particles MPS-SiO that in four-hole boiling flask, adds the 1-1.5g modification
2, add 80-100mL water and 4-5mL monomer DMAEMA again, logical nitrogen 30min; With the air in the eliminating system, the temperature with system rises to 40 ℃ then, adds initiator ammonium persulfate; Under 75 ℃, carry out graft polymerization reaction 10-12h, suction filtration obtains grafting particulate DMAEMA/SiO
2, again in Soxhlet extractor with ethanol extracting 24h, to remove the polymkeric substance of physical adsorption, carry out vacuum-drying then at the grafting microparticle surfaces;
(3), the preparation of silica particle surface molecular engram material: take by weighing 1-1.5g grafting particulate DMAEMA/SiO
2, placing 2000mL concentration is the L-Asp aqueous solution of 0.2-0.3g/L, the pH value of regulation system makes pH=4; Place constant temperature oscillator then, constant-temperature shaking 2.5h makes the abundant swelling of grafted DMAEMA, and the grafting particulate is reached capacity to the absorption of L-Asp; Filtering particles, vacuum-drying, then the saturated grafting particulate that has adsorbed L-Asp of 2.5g being placed concentration is water and the alcohol mixed solvent of the L-Asp of 0.24g/L, water and alcoholic acid volume ratio are 7: 3; The pH value of regulation system makes pH=4, adds the dichloroethyl ether of 0.1-0.12mL, stirs 20-24h down at 35 ℃; Reaction is used the sodium hydroxide solution repetitive scrubbing after finishing, and removes template molecule L-Asp, uses distilled water wash again; Suction filtration, vacuum-drying promptly gets L-Asp molecular surface engram material MIP-PDMAEMA/SiO
2
Said silane coupling agent also can be trimethoxy allyl silicane or trimethoxy vinyl silanes.
The add-on of described initiator ammonium persulfate is the 1-1.2% of monomer mass.
Preparation surface imprinted material MIP-PDMAEMA/SiO
2Preparation process such as Fig. 1 institute not.
Effect proof experiment one:
At first use L-Asp molecular surface engram material MIP-PDMAEMA/SiO
2To racemic modification D; L-Asp solution splits experiment (being the competitive adsorption experiment), and reach the fractionation ability to two kinds of enantiomorphs to investigate its evident characteristics to the L-Asp molecule: compound concentration is about the D of 0.24g/L, L-Asp solution (specific rotation is zero); Get 25mL solution in tool plug Erlenmeyer flask, add the imprinted material MIP-PDMAEMA/SiO of about 0.02g
2, the 2.5h that in constant temperature oscillator, vibrates makes absorption reach balance, and the overall balance concentration of aspartic acid in the determined by ultraviolet spectrophotometry supernatant is adopted in spinning, and measures the specific rotation and the specific rotatory power of supernatant with polarimeter.Use formula (1) to calculate the equilibrium concentration of L-Asp and D-Asp in the solution again, the partition ratio of L-Asp and D-Asp is calculated in then by formula (2).
In the formula, C
D, e(g/L) and C
L, e(g/L) be respectively the equilibrium concentration of two enantiomorphs in the supernatant; [α] is the specific rotatory power of supernatant; [α]
D, markStandard specific rotatory power for enantiomorph D-Asp;
C
Always, e(g/L) be the overall balance concentration of supernatant;
(2)
In the formula, K
d(m Lg
-1) be the partition ratio of a certain enantiomorph; C
e(mgmL
-1) be the equilibrium concentration of this enantiomorph in the supernatant; Q
e(mgg
-1) be the junction at equilibrium resultant of this enantiomorph, Q
eBy formula calculate (3).
C in the formula
0(g/L), C
e(g/L) be respectively the concentration of adsorbing a certain enantiomorph in the solution of front and back, the wherein C of two enantiomorphs
0Be D, 1/2 of L-Asp initial concentration; V (mL) is the adsorption liquid volume; M (g) is imprinted material MIP-PDMAEMA/SiO
2Quality.
By the partition ratio data of two kinds of enantiomorphs in the solution,, calculate imprinted material MIP-PDMAEMA/SiO according to formula (4)
2Selectivity coefficient to L-Asp.
In the formula, k is for enantiomorph D-Asp, imprinted material MIP-PDMAEMA/SiO
2To the selectivity coefficient of L-Asp, the size of k numerical value indicates imprinted material MIP-PDMAEMA/SiO
2To the identification selection property of L-Asp, also be simultaneously to weigh this imprinted material splits ability to two kinds of enantiomorphs yardstick.
Experimental result is as shown in table 1,
Table 1 partition ratio and selectivity coefficient data sheet
Can find from the data of table 1: with respect to D-Asp, imprinted material MIP-PDMAEMA/SiO
2Selectivity coefficient to L-Asp is 3.24.Obviously, competitive experimental result fully discloses: imprinted material MIP-PDMAEMA/SiO
2L-Asp is had high identification selection property, two kinds of enantiomorphs of aspartic acid are had good fractionation ability.Its reason is: imprinted material MIP-PDMAEMA/SiO
2In the polymer foil on surface, be distributed with the trace hole of a large amount of L-Asp, these chirality holes aspect space structure and the action site and the L-Asp molecular configuration be matched, with the configuration of D-Asp then be unmatched; These chirality holes preferentially combine the L-Asp molecule, so L-Asp is demonstrated special identification selection property, D-Asp are then lacked binding ability, make that the two is split.
Effect proof experiment two:
MIP-PDMAEMA/SiO with 0.8g
2Be contained in the Glass tubing that internal diameter is 10mm, (Bed Volume BV) is 2mL to make the bed volume of packed column.Making concentration is that the L-Asp solution of 0.24g/L is with 4BVh
-1The flow velocity adverse current through packed column, collect effluent with the interval of 2BV, measure the concentration of L-Asp in the effluent, draw dynamic binding curve.Adopt same method, making concentration is the racemic modification D of 0.24g/L, and L-Asp solution adverse current is passed through packed column; Effluent is collected at interval with 2BV, measures the total concn of Asp in the effluent, draws dynamic binding curve; As shown in Figure 2, as can be seen from the figure, for MIP-PDMAEMA/SiO
2Packed column, the leakage curve of L-Asp solution obviously is different from the leakage curve of D-Asp solution: (1) D-Asp solution begins to reveal in 62BV, and the leakage volume of L-Asp solution is 72BV then, differs 10BV; (2) D-Asp solution penetrates in 88BV fully, and the penetration volume of L-Asp solution is 100BV; (3) the leakage adsorptive capacity of D-Asp and s-adsorption are 54.10mg/g and 68.95mg/g, and the leakage adsorptive capacity of L-Asp and s-adsorption are 64.22mg/g and 80.28mg/g.The fact of above-mentioned dynamic experiment shows once more, MIP-PDMAEMA/SiO
2L-Asp has been shown tangible identification selection property and good binding affinity, D-Asp has then been lacked identification and binding ability.
Compared with prior art, the present invention has the following advantages:
(1) polymethyl acrylic acid dimethylamino ethyl ester (PDMAEMA) is grafted on silica particle surface, the selection dihalogenated ether is a linking agent, has made the L-Asp molecule is combined the surface imprinted material that speed is fast, identification selection property is strong, binding capacity is high;
(2) use silica matrix, greatly improved the physical strength of imprinted material;
(3) the present invention is suitable for industrial production requirement, and material use efficiency is high, and cost is low, and the L-Asp molecule is had good selectivity and identification and associativity.
Description of drawings
Fig. 1 is preparation surface imprinted material MIP-PDMAEMA/SiO
2The preparation procedure chart;
Fig. 2 is imprinted material MIP-PDMAEMA/SiO
2Dynamic binding curve to L-Asp and D-Asp.
Embodiment
Embodiment 1
A kind of preparation method of novel material of resolving chiral aspartic acid may further comprise the steps:
(1), silica gel surface chemical modification: the 10g activated silica gel is joined in the 130ml water solvent; And coupling agent γ-(methacryloxypropyl) propyl trimethoxy silicane of adding 13ml; React 22h down at 50 ℃; Product behind the suction filtration is used the ethanol repetitive scrubbing, and vacuum-drying makes the aerosil particles MPS-SiO through surface-treated
2
(2), silica particle surface chemical graft polymethyl acrylic acid: the aerosil particles MPS-SiO that in four-hole boiling flask, adds the 1.3g modification
2, add 80mL water and 4.5mL monomer DMAEMA again, logical nitrogen 30min; With the air in the eliminating system, the temperature with system rises to 40 ℃ then, adds initiator ammonium persulfate; The add-on of ammonium persulphate is 1% of a monomer mass; Under 75 ℃, carry out graft polymerization reaction 10h, suction filtration obtains grafting particulate DMAEMA/SiO
2, again in Soxhlet extractor with ethanol extracting 24h, to remove the polymkeric substance of physical adsorption, carry out vacuum-drying then at the grafting microparticle surfaces;
(3), the preparation of silica particle surface molecular engram material: take by weighing 1.3g grafting particulate DMAEMA/SiO
2, placing 2000mL concentration is the L-Asp aqueous solution of 0.25g/L, the pH value of regulation system makes pH=4; Place constant temperature oscillator then, constant-temperature shaking 2.5h makes the abundant swelling of grafted DMAEMA, and the grafting particulate is reached capacity to the absorption of L-Asp; Filtering particles, vacuum-drying, then the saturated grafting particulate that has adsorbed L-Asp of 2.5g being placed concentration is water and the alcohol mixed solvent of the L-Asp of 0.24g/L, water and alcoholic acid volume ratio are 7: 3; The pH value of regulation system makes pH=4, adds the dichloroethyl ether of 0.1mL, stirs 20h down at 35 ℃; Reaction is used the sodium hydroxide solution repetitive scrubbing after finishing, and removes template molecule L-Asp, uses distilled water wash again; Suction filtration, vacuum-drying promptly gets L-Asp molecular surface engram material MIP-PDMAEMA/SiO
2
Embodiment 2
A kind of preparation method of novel material of resolving chiral aspartic acid may further comprise the steps:
(1), silica gel surface chemical modification: the 13g activated silica gel is joined in the 150ml water solvent; And the coupling agent trimethoxy allyl silicane of adding 10ml, reacting 24h down at 50 ℃, the product behind the suction filtration is used the ethanol repetitive scrubbing; Vacuum-drying makes the aerosil particles MPS-SiO through surface-treated
2
(2), silica particle surface chemical graft polymethyl acrylic acid: the aerosil particles MPS-SiO that in four-hole boiling flask, adds the 1.5g modification
2, add 90mL water and 5mL monomer DMAEMA again, logical nitrogen 30min; With the air in the eliminating system, the temperature with system rises to 40 ℃ then, adds initiator ammonium persulfate; The add-on of ammonium persulphate is 1.1% of a monomer mass; Under 75 ℃, carry out graft polymerization reaction 11h, suction filtration obtains grafting particulate DMAEMA/SiO
2, again in Soxhlet extractor with ethanol extracting 24h, to remove the polymkeric substance of physical adsorption, carry out vacuum-drying then at the grafting microparticle surfaces;
(3), the preparation of silica particle surface molecular engram material: take by weighing 1.5g grafting particulate DMAEMA/SiO
2, placing 2000mL concentration is the L-Asp aqueous solution of 0.3g/L, the pH value of regulation system makes pH=4; Place constant temperature oscillator then, constant-temperature shaking 2.5h makes the abundant swelling of grafted DMAEMA, and the grafting particulate is reached capacity to the absorption of L-Asp; Filtering particles, vacuum-drying, then the saturated grafting particulate that has adsorbed L-Asp of 2.5g being placed concentration is water and the alcohol mixed solvent of the L-Asp of 0.24g/L, water and alcoholic acid volume ratio are 7: 3; The pH value of regulation system makes pH=4, adds the dichloroethyl ether of 0.11mL, stirs 24h down at 35 ℃; Reaction is used the sodium hydroxide solution repetitive scrubbing after finishing, and removes template molecule L-Asp, uses distilled water wash again; Suction filtration, vacuum-drying promptly gets L-Asp molecular surface engram material MIP-PDMAEMA/SiO
2
Embodiment 3
A kind of preparation method of novel material of resolving chiral aspartic acid may further comprise the steps:
(1), silica gel surface chemical modification: the 15g activated silica gel is joined in the 100ml water solvent; And the coupling agent trimethoxy vinyl silanes of adding 15ml, reacting 20h down at 50 ℃, the product behind the suction filtration is used the ethanol repetitive scrubbing; Vacuum-drying makes the aerosil particles MPS-SiO through surface-treated
2
(2), silica particle surface chemical graft polymethyl acrylic acid: the aerosil particles MPS-SiO that in four-hole boiling flask, adds the 1g modification
2, add 100mL water and 4mL monomer DMAEMA again, logical nitrogen 30min; With the air in the eliminating system, the temperature with system rises to 40 ℃ then, adds initiator ammonium persulfate; The add-on of ammonium persulphate is 1.2% of a monomer mass; Under 75 ℃, carry out graft polymerization reaction 12h, suction filtration obtains grafting particulate DMAEMA/SiO
2, again in Soxhlet extractor with ethanol extracting 24h, to remove the polymkeric substance of physical adsorption, carry out vacuum-drying then at the grafting microparticle surfaces;
(3), the preparation of silica particle surface molecular engram material: take by weighing 1g grafting particulate DMAEMA/SiO
2, placing 2000mL concentration is the L-Asp aqueous solution of 0.2g/L, the pH value of regulation system makes pH=4; Place constant temperature oscillator then, constant-temperature shaking 2.5h makes the abundant swelling of grafted DMAEMA, and the grafting particulate is reached capacity to the absorption of L-Asp; Filtering particles, vacuum-drying, then the saturated grafting particulate that has adsorbed L-Asp of 2.5g being placed concentration is water and the alcohol mixed solvent of the L-Asp of 0.24g/L, water and alcoholic acid volume ratio are 7: 3; The pH value of regulation system makes pH=4, adds the dichloroethyl ether of 0.12mL, stirs 22h down at 35 ℃; Reaction is used the sodium hydroxide solution repetitive scrubbing after finishing, and removes template molecule L-Asp, uses distilled water wash again; Suction filtration, vacuum-drying promptly gets L-Asp molecular surface engram material MIP-PDMAEMA/SiO
2
Claims (2)
1. the preparation methods of a resolving chiral aspartic acid is characterized in that may further comprise the steps:
(1), silica gel surface chemical modification: the 10-15g activated silica gel is joined in the 100-150ml water solvent; And coupling agent γ-(methacryloxypropyl) propyl trimethoxy silicane of adding 10-15ml; React 20-24h down at 50 ℃; Product behind the suction filtration is used the ethanol repetitive scrubbing, and vacuum-drying makes the aerosil particles MPS-SiO through surface-treated
2
(2), the silica particle surface chemical graft gathers DMAEMA: the aerosil particles MPS-SiO that in four-hole boiling flask, adds the 1-1.5g modification
2, add 80-100mL water and 4-5mL monomer DMAEMA again, logical nitrogen 30min; With the air in the eliminating system, the temperature with system rises to 40 ℃ then, adds initiator ammonium persulfate; Under 75 ℃, carry out graft polymerization reaction 10-12h, suction filtration obtains grafting particulate DMAEMA/SiO
2, again in Soxhlet extractor with ethanol extracting 24h, to remove the polymkeric substance of physical adsorption, carry out vacuum-drying then at the grafting microparticle surfaces;
(3), the preparation of silica particle surface molecular engram material: take by weighing 1-1.5g grafting particulate DMAEMA/SiO
2, placing 2000mL concentration is the L-Asp aqueous solution of 0.2-0.3g/L, the pH value of regulation system makes pH=4; Place constant temperature oscillator then, constant-temperature shaking 2.5h makes the abundant swelling of grafted DMAEMA, and the grafting particulate is reached capacity to the absorption of L-Asp; Filtering particles, vacuum-drying, then the saturated grafting particulate that has adsorbed L-Asp of 2.5g being placed concentration is water and the alcohol mixed solvent of the L-Asp of 0.24g/L, water and alcoholic acid volume ratio are 7:3; The pH value of regulation system makes pH=4, adds the dichloroethyl ether of 0.1-0.12mL, stirs 20-24 h down at 35 ℃; Reaction is used the sodium hydroxide solution repetitive scrubbing after finishing, and removes template molecule L-Asp, uses distilled water wash again; Suction filtration, vacuum-drying promptly gets L-Asp molecular surface engram material MIP-PDMAEMA/SiO
2
2. the preparation methods of resolving chiral aspartic acid according to claim 1, the add-on that it is characterized in that described initiator ammonium persulfate is the 1-1.2% of monomer mass.
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| CN105092682B (en) * | 2015-08-27 | 2017-10-20 | 常州大学 | A kind of electrochemical method for recognizing aspartic acid optical isomer |
| CN105199047B (en) * | 2015-10-30 | 2020-07-07 | 天津工业大学 | Glass fiber with β -cyclodextrin molecularly imprinted polymer loaded on surface |
| CN105801778B (en) * | 2016-02-05 | 2021-01-26 | 新疆维吾尔自治区产品质量监督检验研究院 | Synthetic method of single-layer imprinted polymer based on surface of silicon dioxide microsphere |
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| CN101423612A (en) * | 2008-12-04 | 2009-05-06 | 中北大学 | Method for preparing silica gel surface phenols molecularly imprinted polymer |
| CN101775152A (en) * | 2010-02-25 | 2010-07-14 | 中北大学 | Preparation method of surface imprinted material for matrine substance separation and purification |
| CN101857667A (en) * | 2010-06-10 | 2010-10-13 | 中北大学 | Method for preparing functional particles with high grafting degree |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101423612A (en) * | 2008-12-04 | 2009-05-06 | 中北大学 | Method for preparing silica gel surface phenols molecularly imprinted polymer |
| CN101775152A (en) * | 2010-02-25 | 2010-07-14 | 中北大学 | Preparation method of surface imprinted material for matrine substance separation and purification |
| CN101857667A (en) * | 2010-06-10 | 2010-10-13 | 中北大学 | Method for preparing functional particles with high grafting degree |
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| 陈迎鑫等.功能接枝微粒PDMAEMA/SiO2的制备及其吸附特性初探.《化学通报》.2010,(第11期),1001-1006. * |
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