CN106226381A - The preparation of a kind of Thermo-sensitive quinine chiral sensor and be applied to electrochemical recognition Tryptophan enantiomer - Google Patents
The preparation of a kind of Thermo-sensitive quinine chiral sensor and be applied to electrochemical recognition Tryptophan enantiomer Download PDFInfo
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- CN106226381A CN106226381A CN201610543991.7A CN201610543991A CN106226381A CN 106226381 A CN106226381 A CN 106226381A CN 201610543991 A CN201610543991 A CN 201610543991A CN 106226381 A CN106226381 A CN 106226381A
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- tryptophan
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- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 title claims abstract description 94
- 235000001258 Cinchona calisaya Nutrition 0.000 title claims abstract description 48
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 229960000948 quinine Drugs 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 29
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical class C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 16
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 claims description 9
- 229930182827 D-tryptophan Natural products 0.000 claims description 8
- 238000002474 experimental method Methods 0.000 claims description 8
- 229910052697 platinum Inorganic materials 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical class Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 claims description 6
- 230000005611 electricity Effects 0.000 claims description 4
- 238000000151 deposition Methods 0.000 claims description 3
- 230000008021 deposition Effects 0.000 claims description 3
- 238000004070 electrodeposition Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 11
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 abstract description 5
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 241000157855 Cinchona Species 0.000 description 33
- 235000001014 amino acid Nutrition 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 238000013507 mapping Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 3
- OUYCCCASQSFEME-MRVPVSSYSA-N D-tyrosine Chemical compound OC(=O)[C@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-MRVPVSSYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229940075397 calomel Drugs 0.000 description 2
- 238000005557 chiral recognition Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- 241001660788 Cinchona calisaya Species 0.000 description 1
- 229930195709 D-tyrosine Natural products 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005251 capillar electrophoresis Methods 0.000 description 1
- 238000004850 capillary HPLC Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229910021397 glassy carbon Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 150000003668 tyrosines Chemical class 0.000 description 1
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- 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
-
- 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
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Molecular Biology (AREA)
- Analytical Chemistry (AREA)
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- General Health & Medical Sciences (AREA)
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Abstract
The present invention relates to the preparation of a kind of Thermo-sensitive quinine chiral sensor and be applied to electrochemical recognition Tryptophan enantiomer.Comprise the following steps: the preparation of quinine chiral sensor, electrochemical process identification Tryptophan enantiomer.The invention has the beneficial effects as follows: quinine chiral sensor preparation method is simple, utilizes quinine itself to have this feature of chiral environment, prepare the modified electrode that recognition performance is excellent.At different temperatures, this chiral sensor has contrary recognition effect to L/D tryptophan.
Description
Technical field
The present invention relates to the preparation of a kind of Thermo-sensitive quinine chiral sensor and be applied to electrochemical recognition tryptophan mapping
Body, belongs to biotechnology and electrochemical research field.
Technical background
Chirality is that the base attribute of nature have expressed the asymmetric feature of molecular structure of compounds, is widely present in life
In the fields such as science, medical science, pharmaceutical science and Food Science.Particularly in chiral drug, due to the property of medicine and drug molecule
Stereoeffect is closely related, although the enantiomer of various configuration has identical physical property but metabolism in vivo
There is bigger difference in process, drug effect and toxicity etc., in most cases in chiral drug, only one enantiomer has medicine
Reason is active and another enantiomer does not has activity possibly even to have contrary pharmacological action.
Amino acid whose analysis test always people study more problem.Detect amino acid whose traditional method and mainly have light
Spectrometry (including uv-vis spectra, fluorescence, chemiluminescence etc.) high performance capillary electrophoresis, high performance liquid chromatography and nuclear magnetic resonance, NMR
Method, but the absorption that most of aminoacid is in uv-vis spectra district is the most weak, self unstressed configuration again, it is impossible to directly detect.
These methods typically require and analyte derivativeization process sensitivity and the selectivity improving detection, and operation is complicated, cost is high.In recent years
Coming, electrochemical process detects electroactive aminoacid and has sensitive, low cost easy and simple to handle, pollution-free, sample without pre-treatment because of it
The focus that vast researcher is paid close attention to has been become etc. advantage.
Quinine is a kind of natural alkaloid with chirality, isolated from ledger bark.In such chiral Recognition
In the research of material, quinine has been widely used as parent material in the synthesis of chiral anion crossover fixation phase.
The present invention selects quinine to be that chirality is known as the nitrogen-atoms on electrochemistry chiral Recognition material, its hydroxyl and quinoline ring
Other center, can be used for electrochemical recognition amino acid enantiomer.
Summary of the invention
It is desirable to provide the preparation method of a kind of Thermo-sensitive quinine chiral sensor, and it is applied to electrification knowledge
Other Tryptophan enantiomer.Modifying quinine in glassy carbon electrode surface, Control release temperature, this chiral sensor is to L-/D-color ammonia
Acid has different recognition effects, and recognition performance is excellent.
The preparation of a kind of Thermo-sensitive quinine chiral sensor of the present invention and be applied to electrochemical recognition tryptophan mapping
Body, comprises the following steps:
A, the preparation of quinine chiral sensor: experiment uses three-electrode system, glass-carbon electrode (diameter 3mm) is work electricity
Pole, platinum plate electrode is that saturated calomel electrode (SCE) is reference electrode to electrode, is dipped in quinine solution, applies corresponding electricity
Position, carries out constant potential enrichment and obtains quinine modified electrode；
B, electrochemical process identification Tryptophan enantiomer: experiment uses three-electrode system, and quinine modified electrode is working electrode,
Platinum plate electrode is to electrode, and saturated calomel electrode (SCE) is reference electrode, and the L-/D-tryptophan that it immerses preparation respectively is molten
In liquid, after standing, carry out differential pulse scanning.
The preparation of a kind of Thermo-sensitive quinine chiral sensor of the present invention and be applied to electrochemical recognition tryptophan mapping
Body, further technical scheme can also is that in described step a, and glass-carbon electrode is permanent electricity in the 5mmol/L quinine solution of preparation
Position enrichment, sedimentation potential is-1.0V, and electrodeposition time is 30～1200s.
The preparation of a kind of Thermo-sensitive quinine chiral sensor of the present invention and be applied to electrochemical recognition tryptophan mapping
Body, further technical scheme can also is that, in described step b, quinine modified electrode immerses L-/D-tryptophan solution respectively
Concentration is 0.1～10mmol/L, and time of repose is 6～180s.
The invention has the beneficial effects as follows: quinine chiral sensor preparation method is simple, utilizes quinine itself to have chirality ring
This feature of border, prepares the modified electrode that recognition performance is excellent.At different temperatures, this chiral sensor is to L-/D-tryptophan
Have contrary recognition effect.
Accompanying drawing explanation
The present invention is further described below in conjunction with the accompanying drawings.
Fig. 1 is the recognition effect figure of quinine chiral sensor tryptophan enantiomer in embodiment one；
Fig. 2 is the lab diagram of quinine chiral sensor tryptophan enantiomer at different temperatures in embodiment two；
Fig. 3 is the quinine chiral sensor recognition effect figure to tyrosine enantiomer in comparative example one.
Detailed description of the invention
Presently in connection with specific embodiment, the present invention will be further described, and following example are intended to illustrate rather than
Limitation of the invention further.
Embodiment one:
The preparation of quinine chiral sensor includes following step:
(1) experiment uses three-electrode system, and glass-carbon electrode (diameter 3mm) is working electrode, and platinum plate electrode is to electrode, full
Be reference electrode with calomel electrode (SCE), be dipped in preparation 5mmol/L quinine solution in, by potentiostatic method apply-
The potential deposition 600s of 1.0V, prepares quinine modified electrode.
(2) experiment uses three-electrode system, and quinine modified electrode is working electrode, and platinum plate electrode is to electrode, saturated sweet
Mercury electrode (SCE) is reference electrode, and the concentration that it immerses preparation respectively is in 0.5mmol/L L-/D-tryptophan solution, quiet
Carrying out differential pulse scanning after putting 60s, the recognition effect figure of Tryptophan enantiomer is shown in Fig. 1, it can be seen that this chiral sensor pair
L-Trp has the recognition efficiency of excellence, calculating current ratio (IL/ID=IL-Trp/ID-trp)IL/IDIt is 3.06.
Embodiment two:
The preparation of Thermo-sensitive quinine chiral sensor and be applied to electrochemical recognition Tryptophan enantiomer process and embodiment
One is identical.
At different temperatures, the effect of quinine chiral sensor identification Tryptophan enantiomer is investigated.By preparation
It is in 0.5mmol/L L-/D-tryptophan solution that quinine modified electrode immerses the concentration of preparation respectively, carries out difference after standing 60s
Pulse scans, and experimental temperature is 0～40 DEG C.Under different temperatures, the recognition effect figure of Tryptophan enantiomer is shown in Fig. 2, it can be seen that should
Chiral sensor is at 8 DEG C, preferable to the recognition effect of D-trp；And at 25 DEG C, L-Trp is had the most excellent
Recognition efficiency.
Comparative example one:
The preparation of quinine chiral sensor includes following step:
(1) experiment uses three-electrode system, and glass-carbon electrode (diameter 3mm) is working electrode, and platinum plate electrode is to electrode, full
Be reference electrode with calomel electrode (SCE), be dipped in preparation 5mmol/L quinine solution in, by potentiostatic method apply-
The potential deposition 600s of 1.0V, prepares quinine modified electrode.
(2) experiment uses three-electrode system, and quinine modified electrode is working electrode, and platinum plate electrode is to electrode, saturated sweet
Mercury electrode (SCE) is reference electrode, and the concentration that it immerses preparation respectively is in 0.5mmol/L L-/D-tyrosine solution, quiet
Differential pulse scanning is carried out after putting 60s.As it is shown on figure 3, calculating current ratio (IL/ID=ITYR/ID-Tyrosine)IL/IDIt is 1.02.
The present invention is with quinine for identifying that material prepares chirality sensing membrane modified electrode, compared to other recognition methodss, this method
Simple and easy to do.This chiral sensor has Thermo-sensitive, at different temperatures, L-/D-tryptophan is had contrary recognition effect,
And recognition performance is excellent.
Claims (3)
1. the preparation of Thermo-sensitive quinine chiral sensor and be applied to an electrochemical recognition Tryptophan enantiomer, its feature exists
In: step is as follows:
A, the preparation of quinine chiral sensor: experiment uses three-electrode system, and glass-carbon electrode (diameter 3mm) is working electrode, platinum
Plate electrode is that saturated calomel electrode (SCE) is reference electrode to electrode, is dipped in quinine solution, applies corresponding current potential, enter
The enrichment of row constant potential obtains quinine modified electrode；
B, electrochemical process identification Tryptophan enantiomer: experiment uses three-electrode system, and quinine modified electrode is working electrode, platinized platinum
Electrode is to electrode, and saturated calomel electrode (SCE) is reference electrode, it is immersed in the L-/D-tryptophan solution of preparation respectively,
Differential pulse scanning is carried out after standing.
The preparation of a kind of Thermo-sensitive quinine chiral sensor and be applied to electrochemical recognition tryptophan
Enantiomer, is characterized in that: glass-carbon electrode constant potential enrichment in the 5mmol/L quinine solution of preparation in described step a, deposition electricity
Position is-1.0V, and electrodeposition time is 30～1200s.
The preparation of a kind of Thermo-sensitive quinine chiral sensor and be applied to electrochemical recognition tryptophan
Enantiomer, is characterized in that: in described step b quinine modified electrode immerse respectively the concentration of L-/D-tryptophan solution be 0.1～
10mmol/L, time of repose is 6～180s.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107219277A (en) * | 2017-05-08 | 2017-09-29 | 常州大学 | The preparation of molecular engram overoxidised polypyrrole/poly- p-aminobenzene sulfonic acid modified electrode |
| CN107238644A (en) * | 2017-05-08 | 2017-10-10 | 常州大学 | The silicon dioxide modified indium-tin oxide electrode of branching shape molecular engram is applied to electrochemical recognition Tryptophan enantiomer |
| CN108645900A (en) * | 2018-04-18 | 2018-10-12 | 常州大学 | A kind of preparation method for the glutathione modified electrode can be applied to electrochemistry chiral Recognition |
| CN109265700A (en) * | 2018-10-18 | 2019-01-25 | 辽宁师范大学 | Chiral supermolecule metal phosphonic acid salt crystal material, preparation method and application |
| CN110243897A (en) * | 2019-07-10 | 2019-09-17 | 常州大学 | A kind of preparation of polyethyleneimine/chirality peptide modified glassy carbon electrode and its application in Tryptophan enantiomer Selective recognition |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107219277A (en) * | 2017-05-08 | 2017-09-29 | 常州大学 | The preparation of molecular engram overoxidised polypyrrole/poly- p-aminobenzene sulfonic acid modified electrode |
| CN107238644A (en) * | 2017-05-08 | 2017-10-10 | 常州大学 | The silicon dioxide modified indium-tin oxide electrode of branching shape molecular engram is applied to electrochemical recognition Tryptophan enantiomer |
| CN107238644B (en) * | 2017-05-08 | 2019-06-04 | 常州大学 | The silicon dioxide modified indium-tin oxide electrode of branching shape molecular engram is applied to electrochemical recognition Tryptophan enantiomer |
| CN108645900A (en) * | 2018-04-18 | 2018-10-12 | 常州大学 | A kind of preparation method for the glutathione modified electrode can be applied to electrochemistry chiral Recognition |
| CN109265700A (en) * | 2018-10-18 | 2019-01-25 | 辽宁师范大学 | Chiral supermolecule metal phosphonic acid salt crystal material, preparation method and application |
| CN109265700B (en) * | 2018-10-18 | 2021-06-11 | 辽宁师范大学 | Chiral supermolecule metal phosphonate crystal material, preparation method and application |
| CN110243897A (en) * | 2019-07-10 | 2019-09-17 | 常州大学 | A kind of preparation of polyethyleneimine/chirality peptide modified glassy carbon electrode and its application in Tryptophan enantiomer Selective recognition |
| CN110243897B (en) * | 2019-07-10 | 2021-03-23 | 常州大学 | Selective recognition of tryptophan enantiomer by polyethyleneimine/chiral peptide modified electrode |
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