CN108627556A - A kind of preparation method of the nonionic surfactant self assembly Calixarene Derivatives composite material of Tryptophan enantiomer for identification - Google Patents
A kind of preparation method of the nonionic surfactant self assembly Calixarene Derivatives composite material of Tryptophan enantiomer for identification Download PDFInfo
- Publication number
- CN108627556A CN108627556A CN201810466418.XA CN201810466418A CN108627556A CN 108627556 A CN108627556 A CN 108627556A CN 201810466418 A CN201810466418 A CN 201810466418A CN 108627556 A CN108627556 A CN 108627556A
- Authority
- CN
- China
- Prior art keywords
- self assembly
- brij52
- calixarene derivatives
- preparation
- tryptophan enantiomer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/28—Electrolytic cell components
- G01N27/30—Electrodes, e.g. test electrodes; Half-cells
- G01N27/308—Electrodes, e.g. test electrodes; Half-cells at least partially made of carbon
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/28—Electrolytic cell components
- G01N27/30—Electrodes, e.g. test electrodes; Half-cells
- G01N27/327—Biochemical electrodes, e.g. electrical or mechanical details for in vitro measurements
- G01N27/3275—Sensing specific biomolecules, e.g. nucleic acid strands, based on an electrode surface reaction
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/416—Systems
- G01N27/48—Systems using polarography, i.e. measuring changes in current under a slowly-varying voltage
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Indole Compounds (AREA)
Abstract
The present invention relates to a kind of preparation methods of the nonionic surfactant self assembly Calixarene Derivatives composite material of Tryptophan enantiomer for identification.Include the following steps：It prepares Calixarene Derivatives, the composite material for preparing Calixarene Derivatives and C2 polyoxyethylene ether (Brij52) self assembly, prepare Brij52 self assembly Calixarene Derivatives modified electrode, electrochemical recognition Tryptophan enantiomer.The beneficial effects of the invention are as follows：Preparation method is simple for the modified electrode of Brij52 self assembly Calixarene Derivatives, and preparation process is environment friendly and pollution-free, and the composite material modified electrode can efficiently identify Tryptophan enantiomer.
Description
Technical field
The present invention relates to a kind of nonionic surfactant self assembly calixarenes of Tryptophan enantiomer for identification derivatives
The preparation method of object composite material belongs to biotechnology and electrochemical field.
Technical background
Chiral and chiral analysis is of great significance in terms of modern chemistry and chemical technology.Therefore, exploitation simply intelligence
The enantioselectivity measurement device of energy has become one of the research hotspot of life science and many other related fields.It is most commonly used to
Enantio-selectivity detection be use chromatography and electro transport, these methods it is costly and time consuming.Past ten
The specific isomers of enantioselectivity measurement that develops into of Nian Zhong, chiral electrochemical sensor provide means, use chiral electrification
Sensor is learned, chiral Molecular Recognition event can easily be converted into the significant change of electrochemical signals.
Calixarenes generally refers to the macrocyclic compound being made of methylene-bridged phenol units, is introduced on calixarenes special
Different functional group is by after its derivatization, since the specific electron effect of functional group and the Collaborative Control of Calixarene Derivatives cavity are made
With tending to have good recognition performance to guest molecule or ion.C2 polyoxyethylene ether (Brij52) is a kind of nonionic table
Face activating agent is the main active of liquid detergent, shower cream, metal cleaner, plays emulsification, foaming, decontamination.Brij52
Tryptophan enantiomer can be efficiently identified with the composite material of Calixarene Derivatives self assembly.
Invention content
The purpose of the present invention is to provide a kind of nonionic surfactant self assemblies of Tryptophan enantiomer for identification
The preparation method of Calixarene Derivatives composite material.The composite material modified electrode can efficiently identify Tryptophan enantiomer.
A kind of nonionic surfactant self assembly Calixarene Derivatives composite material of Tryptophan enantiomer for identification
Preparation method, include the following steps：
A, Calixarene Derivatives are prepared：With 4- tertiary butyls p tertButylcalixarene and (R)-N- (2- chloracetyls) 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 Brij52 self assemblies is prepared：Brij52 is dissolved in ultra-pure water, is matched
At certain density Brij52 solution, Calixarene Derivatives are added in above-mentioned solution, self assembly is carried out at a certain temperature, obtains
To the composite material of Calixarene Derivatives and Brij52 self assemblies；
C, the modified electrode of Brij52 self assembly Calixarene Derivatives is prepared：Take Calixarene Derivatives and Brij52 self assemblies
Composite material drop coating in glassy carbon electrode surface, dry at a certain temperature, obtain Brij52 self assembly Calixarene Derivatives
Modified electrode；
D, electrochemical process identifies Tryptophan enantiomer：The modified electrode of Brij52 self assembly Calixarene Derivatives is soaked respectively
Enter in L-/D- tryptophan solutions, after standing a period of time, differential pulse test is carried out with certain speed of sweeping, it will after having surveyed every time
Cyclic voltammetric is swept in the phosphate buffer solution of modified electrode immersion pH=7.0, for restoring electrode activity.
Further, 4- tertiary butyls p tertButylcalixarene and (R)-N- (2- chloracetyls) phenyalanine methyl ester rub in step a
Your proportioning is 1：1.
Further, solvent is absolute methanol in step a, and mixing time is 10~14h.
Further, in step b Brij52 solution a concentration of 0.01~2mM, Calixarene Derivatives a concentration of 1~
10mg/mL。
Further, in step b self assembly temperature be 20 DEG C, the self assembly time be 8~for 24 hours.
Further, it takes 10 μ L composite materials drop coatings in electrode surface in step c, is dried at 20 DEG C.
Further, in step d Tryptophan enantiomer a concentration of 0.1~2.0mM, time of repose be 60~150s.
Further, the number of turns of modified electrode scan cycle volt-ampere in phosphate buffer solution is 2~15 in step d
Circle, it is 8mV/s to sweep speed.
The beneficial effects of the invention are as follows：The preparation method of Brij52 self assembly Calixarene Derivatives modified electrodes is simply easy
Row, preparation process is environment friendly and pollution-free, and the composite material modified electrode tryptophan enantiomer has higher recognition efficiency.
Description of the drawings
This experiment is further illustrated below in conjunction with the accompanying drawings.
Fig. 1 is the difference that Brij52 self assembly Calixarene Derivatives modified electrodes identify Tryptophan enantiomer in embodiment one
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 modified electrode tryptophan enantiomer of Brij52 self assemblies 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
IDL-Trp and D-trp peak current, E are indicated respectivelyLAnd EDL-Trp and D-trp spike potential are indicated respectively.
Embodiment one：
It prepares Calixarene Derivatives and the composite material modified electrode of Brij52 self assemblies is used for electrochemical recognition tryptophan
Enantiomer, including following steps：
(1) using 4- tertiary butyls p tertButylcalixarene, phenyalanine methyl ester is raw material with (R)-N- (2- chloracetyls), mol ratio
It is 1：1, it is stirred to react 12h after 50ml absolute methanols and sodium hydroxide solution is added, synthesizes Calixarene Derivatives.
(2) Brij52 is dissolved in ultra-pure water, is configured to the Brij52 solution of 0.5mM.Take 0.01g Calixarene Derivatives
It is added in Brij52 solution, the self assembly 12h at 20 DEG C obtains the composite material of Calixarene Derivatives and Brij52 self assemblies.
(3) take 10 μ L Calixarene Derivatives and the composite material drop coating of Brij52 self assemblies in glassy carbon electrode surface, 20
It is dried at DEG C, obtains the modified electrode of Brij52 self assembly Calixarene Derivatives.
(4) modified electrode of Brij52 self assembly Calixarene Derivatives is immersed to the L-/D- tryptophan solutions of 0.5mM respectively
In, 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, after having surveyed every time
It is enclosed cyclic voltammetric 5 is swept in the phosphate buffer solution of modified electrode immersion pH=7.0, for restoring electrode activity.Brij52
The differential pulse voltammetry figure of the modified electrode identification Tryptophan enantiomer of self assembly Calixarene Derivatives is shown in attached drawing 1, IL/IDFor
1.17, Δ E are 52mV.
Claims (5)
1. a kind of nonionic surfactant self assembly Calixarene Derivatives composite material of Tryptophan enantiomer for identification
Preparation method, steps are as follows：
A, Calixarene Derivatives are prepared：It is with 4- tertiary butyls p tertButylcalixarene and (R)-N- (2- chloracetyls) 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 C2 polyoxyethylene ether (Brij52) self assembly is prepared：Brij52 is dissolved in super
In pure water, it is made into certain density Brij52 solution, Calixarene Derivatives are added in above-mentioned solution, is carried out at a certain temperature
Self assembly obtains the composite material of Calixarene Derivatives and Brij52 self assemblies；
C, Brij52 self assembly Calixarene Derivatives modified electrodes are prepared：Take the compound of Calixarene Derivatives and Brij52 self assemblies
Droplets of material is applied to glassy carbon electrode surface, dries at a certain temperature, obtains Brij52 self assembly Calixarene Derivatives modified electrodes；
D, electrochemical process identifies Tryptophan enantiomer：The modified electrode of Brij52 self assembly Calixarene Derivatives is immersed respectively
In L-/D- tryptophan solutions, after standing a period of time, differential pulse test is carried out with certain speed of sweeping, will be repaiied after having surveyed every time
Cyclic voltammetric is swept in the phosphate buffer solution of decorations electrode immersion pH=7.0, for restoring electrode activity.
2. the nonionic surfactant self assembly calixarenes of a kind of Tryptophan enantiomer for identification according to claim 1
The preparation method of derivant composite materials, it is characterized in that：4- tertiary butyls p tertButylcalixarene and (R)-N- (2- chloroethenes in the step a
Acyl group) phenyalanine methyl ester mol ratio be 1：1, solvent is absolute methanol, and mixing time is 10~14h.
3. the nonionic surfactant self assembly calixarenes of a kind of Tryptophan enantiomer for identification according to claim 1
The preparation method of derivant composite materials, it is characterized in that：A concentration of 0.01~2mM of Brij52 solution in the step b, cup virtue
A concentration of 1~10mg/mL of hydrocarbon derivative, self assembly temperature be 20 DEG C, the self assembly time be 8~for 24 hours.
4. the nonionic surfactant self assembly calixarenes of a kind of Tryptophan enantiomer for identification according to claim 1
The preparation method of derivant composite materials, it is characterized in that：Take 10 μ L composite materials drop coatings in electrode surface in the step c,
It is dried at 20 DEG C.
5. the nonionic surfactant self assembly calixarenes of a kind of Tryptophan enantiomer for identification according to claim 1
The preparation method of derivant composite materials, it is characterized in that：A concentration of 0.1~2.0mM of Tryptophan enantiomer in the step d,
Time of repose is 60~150s, carries out differential pulse test with the speed of sweeping of 8mV/s, scan cycle lies prostrate in phosphate buffer solution
The number of turns of peace is 2~15 circles.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810466418.XA CN108627556A (en) | 2018-05-16 | 2018-05-16 | A kind of preparation method of the nonionic surfactant self assembly Calixarene Derivatives composite material of Tryptophan enantiomer for identification |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810466418.XA CN108627556A (en) | 2018-05-16 | 2018-05-16 | A kind of preparation method of the nonionic surfactant self assembly Calixarene Derivatives composite material of Tryptophan enantiomer for identification |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN108627556A true CN108627556A (en) | 2018-10-09 |
Family
ID=63693565
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810466418.XA Pending CN108627556A (en) | 2018-05-16 | 2018-05-16 | A kind of preparation method of the nonionic surfactant self assembly Calixarene Derivatives composite material of Tryptophan enantiomer for identification |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108627556A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113702464A (en) * | 2021-09-23 | 2021-11-26 | 上海大学 | P-tau detection immunosensor and preparation and application methods thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101929978A (en) * | 2009-06-24 | 2010-12-29 | 中国科学院电子学研究所 | Self-assembled modified nano gold spherical array bio-sensitive film and preparation method thereof |
| CN102489275A (en) * | 2011-12-26 | 2012-06-13 | 郑州大学 | Phenylalanine-substituted calix [4] arene bonded silica gel stationary phase, preparation method thereof, and application thereof |
| WO2016073172A1 (en) * | 2014-10-21 | 2016-05-12 | Board Of Regents, The University Of Texas System | Methods for sample characterization |
| CN106908500A (en) * | 2017-02-22 | 2017-06-30 | 常州大学 | A kind of preparation and its application of the phenylalanine dipeptide self assembly chiral sensor based on CTAB inductions |
| WO2017145124A1 (en) * | 2016-02-26 | 2017-08-31 | Srm University | A process for electrochemical separation of enantiomers of an amino acid from a racemic mixture |
-
2018
- 2018-05-16 CN CN201810466418.XA patent/CN108627556A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101929978A (en) * | 2009-06-24 | 2010-12-29 | 中国科学院电子学研究所 | Self-assembled modified nano gold spherical array bio-sensitive film and preparation method thereof |
| CN102489275A (en) * | 2011-12-26 | 2012-06-13 | 郑州大学 | Phenylalanine-substituted calix [4] arene bonded silica gel stationary phase, preparation method thereof, and application thereof |
| WO2016073172A1 (en) * | 2014-10-21 | 2016-05-12 | Board Of Regents, The University Of Texas System | Methods for sample characterization |
| WO2017145124A1 (en) * | 2016-02-26 | 2017-08-31 | Srm University | A process for electrochemical separation of enantiomers of an amino acid from a racemic mixture |
| CN106908500A (en) * | 2017-02-22 | 2017-06-30 | 常州大学 | A kind of preparation and its application of the phenylalanine dipeptide self assembly chiral sensor based on CTAB inductions |
Non-Patent Citations (1)
| Title |
|---|
| 张德华: "杯芳烃的功能化及其对氨基酸识别", 《中国优秀硕士学位论文全文数据库（电子期刊）》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113702464A (en) * | 2021-09-23 | 2021-11-26 | 上海大学 | P-tau detection immunosensor and preparation and application methods thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102721727B (en) | Electrochemical sensor based on molecular engram and preparation method and application thereof | |
| CN105044173B (en) | A kind of preparation of the complex film modified electrode of graphene quantum dot/beta cyclodextrin and its applied to electrochemical process recognize Tryptophan enantiomer | |
| CN104020195B (en) | Two identification dopamine trace electrochemical sensor and its preparation method and application | |
| CN103344689B (en) | Based on Fe 3o 4magnetic pole, the preparations and applicatio of-AuNPs magnetic composite nanoparticles immobilization acetylcholinesteraseelectrochemistry | |
| CN102608187B (en) | Preparation method of hollow gold nanometer particle-modified acetylcholinesterase biosensor | |
| CN103454426B (en) | Preparation method of nanogold/chitosan-graphene-methylene blue modified immunosensor | |
| CN104792844A (en) | Preparation of chitosan-carbon quantum dot composite film modified electrode and application of chitosan-carbon quantum dot composite film modified electrode to electrochemical identification of tryptophan enantiomer | |
| CN107490611B (en) | Polyaniline hybridized material of a kind of chirality MOF- and its preparation method and application | |
| CN104330453B (en) | A kind of chiral sensor based on Chitosan-phospholipid complex and preparation method thereof | |
| CN102147389B (en) | Method for testing hydrogen peroxide in cell based on horseradish peroxidase-attapulgite nanometer composite material | |
| CN108645902A (en) | A kind of preparation method of Chiral Calixarenes Derivatives Modified Electrodes for electrochemical process identification Tryptophan enantiomer | |
| CN106501332A (en) | Zn MOFs/ glass-carbon electrodes and preparation method thereof and application | |
| CN108627556A (en) | A kind of preparation method of the nonionic surfactant self assembly Calixarene Derivatives composite material of Tryptophan enantiomer for identification | |
| CN103115949B (en) | Preparation method of enzyme biosensor for detecting pesticide residues | |
| CN106226381A (en) | The preparation of a kind of Thermo-sensitive quinine chiral sensor and be applied to electrochemical recognition Tryptophan enantiomer | |
| CN103913495B (en) | A kind of preparation method detecting the electrode of dopamine | |
| CN104931564A (en) | Preparation method for aptamer sensor modified by multiwall carbon-chitosan/nano ferrous tetroxide-chitosan | |
| CN104655708B (en) | Poly- p-aminobenzene sulfonic acid/trace poly-o-phenylenediamine modified electrode and its preparation method and application | |
| CN110455880A (en) | A kind of L lysine HCL can be used for electrochemistry chiral Recognition induces the preparation method of four pairs of carboxyl phenyl porphyrin self-assemblies | |
| CN108490048A (en) | A kind of preparation method of the chiral sensor of CTAB self assembly calixarenes for electrochemical recognition amino acid enantiomer | |
| CN101576530A (en) | Method for measuring dopamine by utilizing graphite nano-sheet/Nafion composite film to modify electrode | |
| CN106872537B (en) | A kind of three-dimensional flower-shaped cobalt nanometer sheet electrochemical glucose sensor and preparation method thereof | |
| CN107219277B (en) | The preparation of molecular engram overoxidised polypyrrole/poly- p-aminobenzene sulfonic acid modified electrode | |
| CN109342531A (en) | A kind of electrochemical method detecting beta-lactam antibiotic | |
| CN105911128A (en) | Enzyme-free glucose electrochemical sensor and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20181009 |