CN108918621A - A kind of preparation method of the chiral sensor of the CTAB self assembly Calixarene Derivatives for electrochemical recognition Tryptophan enantiomer - Google Patents
A kind of preparation method of the chiral sensor of the CTAB self assembly Calixarene Derivatives for electrochemical recognition Tryptophan enantiomer Download PDFInfo
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Abstract
The present invention relates to a kind of preparation methods of the chiral sensor of CTAB self assembly Calixarene Derivatives for electrochemical recognition Tryptophan enantiomer.Include the following steps：Prepare Calixarene Derivatives, the composite material of preparation Calixarene Derivatives and cetyl trimethylammonium bromide (CTAB) self assembly, preparation CTAB self assembly Calixarene Derivatives chiral sensor, electrochemical recognition Tryptophan enantiomer.The beneficial effects of the invention are as follows：Preparation method is simple for CTAB self assembly Calixarene Derivatives chiral sensor, and preparation process is environment friendly and pollution-free, and the chiral sensor tryptophan enantiomer has preferable recognition efficiency.
Description
Technical field
The present invention relates to a kind of hands of CTAB self assembly Calixarene Derivatives for electrochemical recognition Tryptophan enantiomer
The preparation method of property sensor, belongs to biotechnology and electrochemical field.
Technical background
L-Trp is the important component of synthetic proteins matter, and D-trp is not involved in the synthesis of protein.However,
Nearest D-trp attracts attention because it has great influence to the formation of biomembrane and bacterial growth.Therefore, it designs same
When there is the chiral sensor of highly sensitive recognition effect to L-Trp and D-trp, be great challenge in biochemical analysis field
The task of property.In the chiral Recognition method of report, electrochemical method is widely used.
Calixarenes has the characteristics that conformation is controllable, cavity size is adjustable and upper and lower edge is easy to be chemically modified, and passes through
Various reactions introduce the derivative of the available suitable different application purpose of functional group at its edge, and wherein Chiral Calixarenes spread out
The synthesis of biology and its research of Supramolecular property are research hotspots in recent years.Cetyl trimethylammonium bromide (CTAB) is
A kind of cationic surface active agent is mainly used as the softening agent, emulsifier and antistatic agent of cosmetics.Currently, not reporting
Calixarene Derivatives and CTAB self assembly are used for electrochemical recognition amino acid enantiomer.
Summary of the invention
The purpose of the present invention is to provide a kind of CTAB self assembly calixarenes for electrochemical recognition Tryptophan enantiomer
The preparation method of the chiral sensor of derivative.The chiral sensor tryptophan enantiomer has preferable recognition efficiency.
A kind of chiral sensor of the CTAB self assembly Calixarene Derivatives for electrochemical recognition Tryptophan enantiomer
Preparation method includes the following steps：
A, Calixarene Derivatives are prepared：With 4- tert-butyl p tertButylcalixarene and (R)-N- (2- chloracetyl) phenylalanine first
Ester is raw material, is stirred to react under alkaline condition after suitable solvent is added, and Calixarene Derivatives are synthesized；
B, the composite material of Calixarene Derivatives and cetyl trimethylammonium bromide (CTAB) self assembly is prepared：By CTAB
It is dissolved in ultrapure water, is made into certain density CTAB solution, Calixarene Derivatives is added in above-mentioned solution, in certain temperature
Lower carry out self assembly, obtains the composite material of Calixarene Derivatives Yu CTAB self assembly；
C, CTAB self assembly Calixarene Derivatives chiral sensor is prepared：Take answering for Calixarene Derivatives and CTAB self assembly
Condensation material drop coating is dried at a certain temperature in glassy carbon electrode surface, obtains CTAB self assembly Calixarene Derivatives chirality sensing
Device；
D, electrochemical process identifies Tryptophan enantiomer：CTAB self assembly Calixarene Derivatives chiral sensor is immersed respectively
In L-/D- tryptophan solution, after standing a period of time, differential pulse test is carried out with certain speed of sweeping, it should after having surveyed every time
Cyclic voltammetric is swept in the phosphate buffer solution of chiral sensor immersion pH=7.0, for restoring electrode activity.
Further, 4- tert-butyl p tertButylcalixarene and (R)-N- (2- chloracetyl) phenyalanine methyl ester rub in step a
Your proportion is 1：1.
Further, solvent is anhydrous methanol in step a, and mixing time is 10~14h.
Further, the concentration of CTAB solution is 0.01~1mM in step b, the concentration of Calixarene Derivatives is 1~
10mg/mL。
Further, in step b self assembly temperature be 4 DEG C, the self assembly time be 6~for 24 hours.
Further, it takes 10 μ L composite material drop coatings in electrode surface in step c, is dried at 4 DEG C.
Further, the concentration of Tryptophan enantiomer is 0.1~2.0mM in step d, and time of repose is 30~150s.
Further, the circle number of scan cycle volt-ampere is 5~15 circles in phosphate buffer solution in step d, and sweeping speed is
8mV/s。
The beneficial effects of the invention are as follows：The preparation method of CTAB self assembly Calixarene Derivatives chiral sensor is simply easy
Row, preparation process is environment friendly and pollution-free, and the chiral sensor tryptophan enantiomer has preferable recognition efficiency.
Detailed description of the invention
This experiment is further illustrated with reference to the accompanying drawing.
Fig. 1 is the difference that CTAB self assembly Calixarene Derivatives chiral sensor identifies Tryptophan enantiomer in embodiment one
Pulse Voltammetry figure.
Fig. 2 is CTAB self assembly Calixarene Derivatives chiral sensor tryptophan mapping at different pH in embodiment two
The recognition effect figure of body.
Fig. 3 is the difference that the not derivative calixarenes chiral sensor of CTAB self assembly identifies Tryptophan enantiomer in comparative example one
Pulse Voltammetry figure.
Specific embodiment
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 chiral sensor tryptophan enantiomer of CTAB self assembly Calixarene Derivatives of the present invention is as follows
It is identified：
RL/D=IL/ID
Δ E=ED-EL
In formula, RL/DIndicate that Tryptophan enantiomer peak current ratio, Δ E indicate Tryptophan enantiomer spike potential difference, ILWith
IDRespectively indicate L-Trp and D-trp peak current, ELAnd EDRespectively indicate L-Trp and D-trp spike potential.
Embodiment one：
The chiral sensor for preparing Calixarene Derivatives and CTAB self assembly is used for electrochemical recognition Tryptophan enantiomer, packet
Include following steps：
(1) using 4- tert-butyl p tertButylcalixarene and (R)-N- (2- chloracetyl), phenyalanine methyl ester is raw material, mol ratio
It is 1：1, it is stirred to react 12h after 50ml anhydrous methanol and sodium hydroxide solution is added, synthesizes Calixarene Derivatives.
(2) CTAB is dissolved in ultrapure water, is configured to the CTAB solution of 0.6mM.0.01g Calixarene Derivatives are taken to be added
In CTAB solution, the self assembly 12h at 4 DEG C obtains the composite material of Calixarene Derivatives Yu CTAB self assembly.
(3) take 10 μ L Calixarene Derivatives and the composite material drop coating of CTAB self assembly in glassy carbon electrode surface, at 4 DEG C
It dries, obtains CTAB self assembly Calixarene Derivatives chiral sensor.
(4) CTAB self assembly Calixarene Derivatives chiral sensor is immersed respectively in the L-/D- tryptophan solution of 1mM,
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, it will after having surveyed every time
The circle of cyclic voltammetric 5 is swept in the phosphate buffer solution of chiral sensor immersion pH=7.0, for restoring electrode activity.CTAB
The differential pulse voltammetry figure of self assembly Calixarene Derivatives chiral sensor identification Tryptophan enantiomer is shown in attached drawing 1, IL/IDFor
35.75。
Embodiment two：
Preparation CTAB self assembly Calixarene Derivatives chiral sensor is wrapped for identifying Tryptophan enantiomer at different pH
Include following steps：
(1) CTAB is dissolved in ultrapure water, is configured to the CTAB solution of 0.6mM.0.01g Calixarene Derivatives are taken to be added
In CTAB solution, the self assembly 12h at 4 DEG C obtains the composite material of Calixarene Derivatives Yu CTAB self assembly.
(2) take 10 μ L Calixarene Derivatives and the composite material drop coating of CTAB self assembly in glassy carbon electrode surface, at 4 DEG C
It dries, obtains CTAB self assembly Calixarene Derivatives chiral sensor.
(3) CTAB self assembly Calixarene Derivatives chiral sensor is immersed respectively in the L-/D- tryptophan solution of 1mM,
PH range is 5.5~8.0, after standing 90s, in the potential range of 0.4~1.2V, carries out differential pulse with the speed of sweeping of 8mV/s
The chiral sensor is immersed in the phosphate buffer solution of corresponding pH after having surveyed every time and sweeps cyclic voltammetric 5 and enclose by test, is used to extensive
Overlying electrode activity.CTAB self assembly Calixarene Derivatives chiral sensor identifies the lab diagram of Tryptophan enantiomer at different pH
See attached drawing 2, it is seen that CTAB self assembly Calixarene Derivatives chiral sensor in pH=7, imitate by the identification of tryptophan enantiomer
Fruit is best.
Comparative example one：
The not derivative calixarenes chiral sensor of CTAB self assembly is prepared for electrochemical recognition Tryptophan enantiomer, including with
Under several steps：
(1) CTAB is dissolved in ultrapure water, is configured to the CTAB solution of 0.6mM.Take 3mM 4- tert-butyl p tertButylcalixarene
Powder is added in CTAB solution, and the self assembly 12h at 4 DEG C obtains 4- tert-butyl p tertButylcalixarene-CTAB composite material.
(2) it takes 10 μ L 4- tert-butyl p tertButylcalixarene-CTAB composite material drop coatings in glassy carbon electrode surface, dries in the air at 4 DEG C
It is dry, obtain 4- tert-butyl p tertButylcalixarene-CTAB chiral sensor.
(3) 4- tert-butyl p tertButylcalixarene-CTAB chiral sensor is immersed respectively in the L-/D- tryptophan solution of 1mM,
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, it will after having surveyed every time
The circle of cyclic voltammetric 5 is swept in the phosphate buffer solution of chiral sensor immersion pH=7.0, for restoring electrode activity.Uncle 4-
The differential pulse voltammetry figure of butyl cup [4] aromatic hydrocarbons-CTAB chiral sensor identification Tryptophan enantiomer is shown in attached drawing 3, IL/IDFor
19.42。
Claims (5)
1. a kind of system of the chiral sensor of the CTAB self assembly Calixarene Derivatives for electrochemical recognition Tryptophan enantiomer
Preparation Method, steps are as follows：
A, Calixarene Derivatives are prepared：It is with 4- tert-butyl p tertButylcalixarene and (R)-N- (2- chloracetyl) phenyalanine methyl ester
Raw material is stirred to react under alkaline condition after suitable solvent is added, and synthesizes Calixarene Derivatives；
B, the composite material of Calixarene Derivatives and cetyl trimethylammonium bromide (CTAB) self assembly is prepared：CTAB is dissolved
In ultrapure water, be made into certain density CTAB solution, Calixarene Derivatives be added in above-mentioned solution, at a certain temperature into
Row self assembly obtains the composite material of Calixarene Derivatives Yu CTAB self assembly；
C, CTAB self assembly Calixarene Derivatives chiral sensor is prepared：Take the composite wood of Calixarene Derivatives Yu CTAB self assembly
Drop is applied to glassy carbon electrode surface, dries at a certain temperature, obtains CTAB self assembly Calixarene Derivatives chiral sensor；
D, electrochemical process identifies Tryptophan enantiomer：By CTAB self assembly Calixarene Derivatives chiral sensor immerse respectively L-/
In D-trp solution, after standing a period of time, differential pulse test is carried out with certain speed of sweeping, by the chirality after having surveyed every time
Cyclic voltammetric is swept in the phosphate buffer solution of sensor immersion pH=7.0, for restoring electrode activity.
2. a kind of CTAB self assembly Calixarene Derivatives for electrochemical recognition Tryptophan enantiomer according to claim 1
Chiral sensor preparation method, it is characterized in that：4- tert-butyl p tertButylcalixarene and (R)-N- (2- chloracetyl in the step a
Base) phenyalanine methyl ester mol ratio be 1：1, solvent is anhydrous methanol, and mixing time is 10~14h.
3. a kind of CTAB self assembly Calixarene Derivatives for electrochemical recognition Tryptophan enantiomer according to claim 1
Chiral sensor preparation method, it is characterized in that：The concentration of CTAB solution is 0.01~1mM in the step b, and calixarenes spreads out
Biology concentration be 1~10mg/mL, self assembly temperature be 4 DEG C, the self assembly time be 6~for 24 hours.
4. a kind of CTAB self assembly Calixarene Derivatives for electrochemical recognition Tryptophan enantiomer according to claim 1
Chiral sensor preparation method, it is characterized in that：Take 10 μ L composite material drop coatings in electrode surface in the step c, at 4 DEG C
Under dry.
5. a kind of CTAB self assembly Calixarene Derivatives for electrochemical recognition Tryptophan enantiomer according to claim 1
Chiral sensor preparation method, it is characterized in that：The concentration of Tryptophan enantiomer is 0.1~2.0mM in the step d, quiet
Setting the time is 30~150s, carries out differential pulse test, the scan cycle volt-ampere in phosphate buffer solution with the speed of sweeping of 8mV/s
Circle number be 5~15 circle.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109959690A (en) * | 2019-04-12 | 2019-07-02 | 常州大学 | A kind of preparation method of the cyclohexane cyclohexanedimethanodibasic Derivatives Modified Electrodes for electrochemical recognition Tryptophan enantiomer |
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