CN108490048A - A kind of preparation method of the chiral sensor of CTAB self assembly calixarenes for electrochemical recognition amino acid enantiomer - Google Patents
A kind of preparation method of the chiral sensor of CTAB self assembly calixarenes for electrochemical recognition amino acid enantiomer Download PDFInfo
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- CN108490048A CN108490048A CN201810220400.1A CN201810220400A CN108490048A CN 108490048 A CN108490048 A CN 108490048A CN 201810220400 A CN201810220400 A CN 201810220400A CN 108490048 A CN108490048 A CN 108490048A
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Abstract
The present invention relates to a kind of preparation methods of the chiral sensor of the CTAB self assembly calixarenes for electrochemical recognition amino acid enantiomer.Include the following steps:It prepares calixarenes CTAB composite materials, prepare calixarenes CTAB composite materials modified electrode, electrochemical recognition amino acid enantiomer.The beneficial effects of the invention are as follows:Preparation method is simple for CTAB self assembly calixarenes composite materials modified electrode, and preparation process is environment friendly and pollution-free, and the composite material modified electrode has and significantly promoted compared to individual calixarenes modified electrode for the recognition efficiency of amino acid enantiomer.
Description
Technical field
The present invention relates to a kind of chirality sensings of CTAB self assembly calixarenes for electrochemical recognition amino acid enantiomer
The preparation method of device belongs to biotechnology and Electroanalytical Chemistry field.
Technical background
Protein is the material base of life, is the basic organic matter for constituting cell, is the main undertaker of vital movement,
And amino acid is the basic composition unit of protein, is the molecule component of life, is played in many related fields such as life system
Vital effect.Amino acids all have chiral greatly, and the physiological action of D- types and L-type enantiomer is completely different.Protein
Almost entirely by L-type Amino acid profile, and its structure is corresponding with various physiological activity in organism.Currently used for amino acid hand
Property identification technology it is very much, electrochemical process is easy to miniature because of its high sensitivity, quick, real-time, at low cost, easy to operate, instrument
The advantages that change and it is interested to researchers.
Calixarenes is a kind of cyclic oligomer constituted by connection at phenolic hydroxyl group ortho position by methylene by phenol units.From
From structure, it has the cavity structure similar to cyclodextrin and crown ether, and the inside of cavity is phenyl ring electron cloud high concentration
The upper limb opening in region, cup is small, is highly polar hydroxyl, the lower part of cup is lipophilic hydrocarbyl portion.Since it has size
Adjustable hydrophobic cavity, and with multiple active phenolic hydroxyl groups and the easy phenyl ring that parental materials occur, pass through repairing for cup top
The variation of decorations and phenolic hydroxyl group functional group, can be obtained the derivative of various structures.Cetyl trimethylammonium bromide (CTAB) is one
Kind cationic surface active agent, is mainly used as the softening agent, emulsifier and antistatic agent of cosmetics, after calixarenes self assembly
The dissolubility of calixarenes in aqueous solution can be improved.Currently, calixarenes and CTAB self assemblies are used for electrochemical recognition amino acid
The report of enantiomer is seldom.
Invention content
The purpose of the present invention is to provide a kind of CTAB self assembly calixarenes for electrochemical recognition amino acid enantiomer
Chiral sensor preparation method.CTAB self assembly calixarenes composite material modified electrodes can efficiently identify amino acid mapping
Body.
A kind of preparation side of the chiral sensor of CTAB self assembly calixarenes for electrochemical recognition amino acid enantiomer
Method includes the following steps:
A, calixarenes-CTAB composite materials are prepared:CTAB is dissolved in ultra-pure water, it is molten to be made into certain density CTAB
Calixarenes powder is added in above-mentioned solution, carries out self assembly at a certain temperature, obtain calixarenes-CTAB composite materials by liquid;
B, calixarenes-CTAB composite material modified electrodes are prepared:Take the composite material drop coating of CTAB self assembly calixarenes in
Glassy carbon electrode surface is dried at a certain temperature, obtains calixarenes-CTAB composite material modified electrodes;
C, electrochemical recognition amino acid enantiomer:Calixarenes-CTAB composite materials modified electrode is immersed into L-/D- ammonia respectively
In base acid solution, after standing a period of time, differential pulse test is carried out with certain speed of sweeping, soaks modified electrode after having surveyed every time
Enter in the phosphate buffer solution of pH=7.0 and sweep cyclic voltammetric, for restoring electrode activity.
Further, in step a CTAB solution a concentration of 0.1~10mM, a concentration of 1.0~5.0mM of calixarenes.
Further, self assembly temperature is 4 DEG C in step a, and the self assembly time is 8~48h.
Further, it takes 10 μ L calixarenes-CTAB composite materials drop coatings in electrode surface in step b, is dried at 4 DEG C.
Further, in step c amino acid enantiomer a concentration of 0.5~3.0mM, time of repose be 60~180s.
Further, the number of turns of scan cycle volt-ampere is 2~15 circles in phosphate buffer solution in step c, and sweeping speed is
8mV/s。
The beneficial effects of the invention are as follows:The preparation method of CTAB self assembly calixarenes composite material modified electrodes is simply easy
Row, preparation process is environment friendly and pollution-free, and the composite material modified electrode compares individually the recognition efficiency of amino acid enantiomer
Calixarenes modified electrode have and significantly promoted.
Description of the drawings
This experiment is further illustrated below in conjunction with the accompanying drawings.
Fig. 1 is the atomic force microscopy diagram of calixarenes-CTAB composite materials.
Fig. 2 is the FTIR spectrum figure of calixarenes, CTAB and calixarenes-CTAB composite materials.
Fig. 3 is the differential pulse that calixarenes-CTAB composite material modified electrodes identify Tryptophan enantiomer in embodiment one
Voltammogram.
Fig. 4 is the differential pulse that calixarenes-CTAB composite material modified electrodes identify tyrosine enantiomer in embodiment two
Voltammogram.
Fig. 5 is that the composite material modified electrode of the CTAB self assembly calixarenes of various concentration in embodiment three identifies tryptophan
The design sketch of enantiomer.
Fig. 6 is the differential pulse voltammetry figure that calixarenes modified electrode identifies Tryptophan enantiomer in comparative example one.
Fig. 7 is that CTAB self assembly calixarenes composite material modified electrodes identify Tryptophan enantiomer under room temperature in comparative example two
Differential pulse voltammetry figure.
Specific implementation mode
Presently in connection with specific embodiment, the present invention will be further described, following embodiment be intended to illustrate invention rather than
Limitation of the invention further.
The composite material modified electrode of CTAB self assemblies calixarenes of the present invention to amino acid enantiomer as follows
It is identified:
RL/D=IL/ID
Δ E=ED-EL
In formula, RL/DIndicate that the peak current ratio of amino acid enantiomer, Δ E indicate the spike potential difference of amino acid enantiomer,
ILAnd IDThe peak current of l-amino acid and D- amino acid, E are indicated respectivelyLAnd EDThe peak of l-amino acid and D- amino acid is indicated respectively
Current potential.
Embodiment one:
It prepares calixarenes-CTAB composite material modified electrodes and is used for electrochemical recognition Tryptophan enantiomer, including is following several
A step:
(1) CTAB is dissolved in ultra-pure water, is configured to the CTAB solution of 0.6mM.Take 3mM 4- tert-butyl-calixes [4] fragrant
Hydrocarbon powder is added in CTAB solution, and the self assembly 12h at 4 DEG C obtains 4- tertiary butyl p tertButylcalixarene-CTAB composite materials.
(2) it takes 10 μ L 4- tertiary butyl p tertButylcalixarene-CTAB composite materials drop coatings in glassy carbon electrode surface, dries in the air at 4 DEG C
It is dry, obtain 4- tertiary butyl p tertButylcalixarene-CTAB composite material modified electrodes.
(3) the L-/D- tryptophans that 4- tertiary butyl p tertButylcalixarene-CTAB composite materials modified electrodes are immersed to 1mM respectively are molten
In liquid, after standing 90s, in the potential range of 0.4~1.2V, differential pulse test is carried out with the speed of sweeping of 8mV/s, has been surveyed every time
Cyclic voltammetric 5 will be swept in the phosphate buffer solution of modified electrode immersion pH=7.0 afterwards to enclose, for restoring electrode activity.Uncle 4-
The differential pulse voltammetry figure of butyl cup [4] aromatic hydrocarbons-CTAB composite material modified electrodes identification Tryptophan enantiomer is shown in attached drawing 3, IL/
IDIt is 19.42.
Embodiment two:
It prepares calixarenes-CTAB composite material modified electrodes and is used for electrochemical recognition tyrosine enantiomer, including is following several
A step:
(1) CTAB is dissolved in ultra-pure water, is configured to the CTAB solution of 0.6mM.Take 3mM 4- tert-butyl-calixes [4] fragrant
Hydrocarbon powder is added in CTAB solution, and the self assembly 12h at 4 DEG C obtains 4- tertiary butyl p tertButylcalixarene-CTAB composite materials.
(2) it takes 10 μ L 4- tertiary butyl p tertButylcalixarene-CTAB composite materials drop coatings in glassy carbon electrode surface, dries in the air at 4 DEG C
It is dry, obtain 4- tertiary butyl p tertButylcalixarene-CTAB composite material modified electrodes.
(3) the L-/D- tyrosine that 4- tertiary butyl p tertButylcalixarene-CTAB composite materials modified electrodes are immersed to 1mM respectively is molten
In liquid, after standing 90s, in the potential range of 0.4~1.2V, differential pulse test is carried out with the speed of sweeping of 8mV/s, has been surveyed every time
Cyclic voltammetric 5 will be swept in the phosphate buffer solution of modified electrode immersion pH=7.0 afterwards to enclose, for restoring electrode activity.Uncle 4-
The differential pulse voltammetry figure of butyl cup [4] aromatic hydrocarbons-CTAB composite material modified electrodes identification tyrosine enantiomer is shown in attached drawing 4, IL/
IDIt is 2.79.
Embodiment three:
The composite material modified electrode of the CTAB self assembly calixarenes of various concentration Tryptophan enantiomer for identification is prepared,
Including following steps:
(1) CTAB being dissolved in ultra-pure water, is configured to the CTAB solution of various concentration, experimental concentration is 0.2~
5.0mM.3mM 4- tertiary butyl p tertButylcalixarene powder is taken to be added in the CTAB solution of various concentration respectively, the self assembly at 4 DEG C
12h obtains 4- tertiary butyl p tertButylcalixarene-CTAB composite materials.
(2) take 10 μ L 4- tertiary butyl p tertButylcalixarene-CTAB composite materials drop coatings in glassy carbon electrode surface respectively, at 4 DEG C
Under dry, obtain 4- tertiary butyl p tertButylcalixarene-CTAB composite material modified electrodes.
(3) the L-/D- tryptophans that 4- tertiary butyl p tertButylcalixarene-CTAB composite materials modified electrodes are immersed to 1mM respectively are molten
In liquid, after standing 90s, in the potential range of 0.4~1.2V, differential pulse test is carried out with the speed of sweeping of 8mV/s, has been surveyed every time
Cyclic voltammetric 5 will be swept in the phosphate buffer solution of modified electrode immersion pH=7.0 afterwards to enclose, for restoring electrode activity.It is different
The design sketch of the composite material modified electrode identification Tryptophan enantiomer of the CTAB self assembly 4- tertiary butyl p tertButylcalixarenes of concentration is shown in
Attached drawing 5, it is seen that 4- tertiary butyl p tertButylcalixarene-CTAB composite materials modified electrodes tryptophan pair in a concentration of 0.6mM of CTAB
The recognition effect for reflecting body is best, IL/IDIt is 19.42.
Comparative example one:
Calixarenes modified electrode is prepared for electrochemical recognition Tryptophan enantiomer, including following steps:
(1) 4- tertiary butyl p tertButylcalixarenes are pulverized into last ultrasonic disperse in ultra-pure water, is configured to uncle 4- of 3mM
Butyl cup [4] aromatic hydrocarbons dispersion liquid.It takes 10 μ L drop coatings in glassy carbon electrode surface, dries at room temperature, obtain 4- tert-butyl-calixes [4] virtue
Hydrocarbon modified electrode.
(2) it is working electrode that experiment, which uses three-electrode system, 4- tertiary butyl p tertButylcalixarene modified electrodes, and platinum plate electrode is
To electrode, saturated calomel electrode is reference electrode, and the 1.0mM L-/D- tryptophans which is immersed to preparation respectively are molten
In liquid, after standing 90s, in the potential range of 0.4~1.2V, differential pulse test is carried out with the speed of sweeping of 8mV/s, has been surveyed every time
Cyclic voltammetric 5 will be swept in the phosphate buffer solution of modified electrode immersion pH=7.0 afterwards to enclose, for restoring electrode activity.Uncle 4-
The recognition effect figure of butyl cup [4] aromatic hydrocarbons modified electrode tryptophan enantiomer is shown in attached drawing 6, IL/IDIt is 7.65.
Comparative example two:
Prepare under room temperature CTAB self assemblies calixarenes composite material modified electrode Tryptophan enantiomer for identification, including with
Under several steps:
(1) CTAB is dissolved in ultra-pure water, is configured to the CTAB solution of 0.6mM.Take 3mM 4- tert-butyl-calixes [4] fragrant
Hydrocarbon powder is added in CTAB solution, and self assembly 12h, obtains 4- tertiary butyl p tertButylcalixarene-CTAB composite materials at normal temperatures.
(2) it takes 10 μ L 4- tertiary butyl p tertButylcalixarene-CTAB composite materials drop coatings in glassy carbon electrode surface, dries in the air at normal temperatures
It is dry, obtain 4- tertiary butyl p tertButylcalixarene-CTAB composite material modified electrodes.
(3) the L-/D- tryptophans that 4- tertiary butyl p tertButylcalixarene-CTAB composite materials modified electrodes are immersed to 1mM respectively are molten
In liquid, after standing 90s, in the potential range of 0.4~1.2V, differential pulse test is carried out with the speed of sweeping of 8mV/s, has been surveyed every time
Cyclic voltammetric 5 will be swept in the phosphate buffer solution of modified electrode immersion pH=7.0 afterwards to enclose, for restoring electrode activity.This is multiple
The differential pulse voltammetry figure of condensation material modified electrode identification Tryptophan enantiomer is shown in attached drawing 7, IL/IDIt is 9.45.
Claims (4)
1. a kind of preparation method of the chiral sensor of CTAB self assembly calixarenes for electrochemical recognition amino acid enantiomer,
Steps are as follows:
A, the composite material of calixarenes-CTAB is prepared:CTAB is dissolved in ultra-pure water, certain density CTAB solution is made into,
Calixarenes powder is added in above-mentioned solution, self assembly is carried out at a certain temperature, obtains calixarenes-CTAB composite materials;
B, calixarenes-CTAB composite material modified electrodes are prepared:Take calixarenes-CTAB composite materials drop coating in glass-carbon electrode table
Face is dried at a certain temperature, obtains calixarenes-CTAB composite material modified electrodes;
C, electrochemical process identifies amino acid enantiomer:Calixarenes-CTAB composite materials modified electrode is immersed into L-/D- amino respectively
In acid solution, after standing a period of time, differential pulse test is carried out with certain speed of sweeping, immerses modified electrode after having surveyed every time
Cyclic voltammetric is swept in the phosphate buffer solution of pH=7.0, for restoring electrode activity.
2. the chirality of a kind of CTAB self assembly calixarenes for electrochemical recognition amino acid enantiomer according to claim 1
The preparation method of sensor, it is characterized in that:A concentration of 0.1~10mM of CTAB solution in the step a, calixarenes it is a concentration of
1.0~5.0mM, self assembly temperature are 4 DEG C, and the self assembly time is 8~48h.
3. the chirality of a kind of CTAB self assembly calixarenes for electrochemical recognition amino acid enantiomer according to claim 1
The preparation method of sensor, it is characterized in that:Take 10 μ L calixarenes-CTAB composite materials drop coatings in electrode surface in the step b,
It is dried at 4 DEG C.
4. the chirality of a kind of CTAB self assembly calixarenes for electrochemical recognition amino acid enantiomer according to claim 1
The preparation method of sensor, it is characterized in that:A concentration of 0.5~3.0mM of amino acid enantiomer, time of repose in the step c
For 60~180s, differential pulse test, the number of turns of scan cycle volt-ampere in phosphate buffer solution are carried out with the speed of sweeping of 8mV/s
For 2~15 circles.
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CN110591105A (en) * | 2019-09-05 | 2019-12-20 | 常州大学 | Preparation and application of rotaxane molecule with electrochemical activity |
CN110779972A (en) * | 2019-09-24 | 2020-02-11 | 重庆东渝中能实业有限公司 | Electrochemical detection method of trace vitamin B9 |
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