CN105067686A - Selectivity identification of poly L-glutamic acid/amylose-modified glassy carbon electrode on tryptophan enantiomer - Google Patents
Selectivity identification of poly L-glutamic acid/amylose-modified glassy carbon electrode on tryptophan enantiomer Download PDFInfo
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Abstract
The invention relates to selectivity identification of a poly L-glutamic acid/amylose-modified glassy carbon electrode on a tryptophan enantiomer. The selectivity identification comprises the following steps: preparation of the poly L-glutamic acid-modified glassy carbon electrode, preparation of poly L-glutamic acid/amylose-modified glassy carbon electrode and selectivity identification on the tryptophan enantiomer. The selectivity identification has the beneficial effect that the preparation method of the poly L-glutamic acid/amylose-modified glassy carbon electrode is simple, fast and has advantage of no pollution, the modification electrode has good identification effect on the tryptophan enantiomer, which attributes to stereoselectivity of amylose to the tryptophan enantiomer.
Description
Technical field
The present invention relates to the Selective recognition of L-glutamic acid/amylose modified glassy carbon electrode tryptophan enantiomorph, belong to electrochemical sensor and molecular recognition field.
Technical background
Material such as protein, polysaccharide, nucleic acid, the amino acid etc. formed in real life in vital movement are nearly all have chirality.For chipal compounds, when there is not outside chiral environment, two enantiomorphs, except optical activity, have identical chemistry and physical property, it shows as identical fusing point, solubleness, infrared spectrum, nuclear magnetic resoance spectrum, and gas phase and liquid chromatography also have identical retention time.But when chipal compounds is in chiral environment, two optical isomers just show different behaviors, cause different performances.As chiral drug, because its spatial configuration is different, also just there is different pharmacology and medicine efficacy relation from the interaction between acceptor; The stereoselectivity of biochemical reaction process, all kinds of natural spatial configuration of organic chiral compound, the spatial configuration of macromolecular material etc. are all relevant with the spatial configuration of chiral molecules, biologically active, visible, the research of chiral Recognition has important theory and practical study meaning.At present, chiral Recognition research method mainly comprises chiral chromatogram, spectrum and galvanochemistry chiral sensor.Wherein chromatographic process has been widely used in compartment analysis chipal compounds, and prove a kind of effective chiral analysis method, but also there is certain shortcoming in the method, such as than being easier to the change of configuration or the inactivation that cause biological species chiral selector and analysis of compounds, and instrument cost is high, analysis time is long, is difficult to especially realize original position and on-line checkingi etc.Electrochemical sensor, because its preparation is simple, cost is low, recognition efficiency advantages of higher, is used for identifying that chiral material has researching value very widely.
Amino acid chiral identification is significant to protein chemistry, biological chemistry and whole life science and product development, quality control and production management etc.Amino acid has close relationship with biological vital movement, and large amino acids has chiral isomer.The physiological action of D-type and L-type enantiomorph is totally different, and L-type amino acid is amino acid needed by human body, and excess intake D-type amino acid can cause poisoning.In nutrition, D-type seems nonsensical, but the favor of its extremely medical personal, and as in amino acids microbiotic, D-type amino acid is difficult to by degradation by bacteria, and unlikelyly develops immunity to drugs.This provides more wide prospect by for antibiotic utilization undoubtedly.All these relates to the fractionation problem of chiral amino acid, prepares pure chipal compounds all significant in fields such as life science, pharmaceutical chemistry, fine chemistries, enjoys the attention of chemist, life scholar.Therefore it is particularly important to adopt that suitable technology identifies accurately to it, isolation andpurification seems.
Amylose is polymeric carbohydrate, is a kind of natural polysaccharide.Amylose is that D-six ring glucose forms through α-Isosorbide-5-Nitrae-glycosidic bond, is double-spiral structure.Starch, as a kind of important raw material of industry, is widely used in the industries such as food, chemical industry, weaving and building materials.Amylose has good film forming, and its molecule has abundant-OH, thus makes amylose have the effect such as ion chelating, absorption to many ions, organism and biomolecule, and amylose and derivant thereof can be used as chiral Recognition material.
Summary of the invention
For Problems existing in technical background, the object of the invention is the Selective recognition by L-glutamic acid/amylose modified glassy carbon electrode tryptophan enantiomorph.
The technical solution adopted for the present invention to solve the technical problems is: the Selective recognition of L-glutamic acid/amylose modified glassy carbon electrode tryptophan enantiomorph, comprises the following steps:
A, prepare L-glutamic acid modified glassy carbon electrode: preparation Pidolidone solution (solvent is 0.1 ~ 0.3M sodium dihydrogen phosphate, pH=6 ~ 7), adopt cyclic voltammetry to be deposited on glassy carbon electrode surface, obtain L-glutamic acid modified glassy carbon electrode.
B, prepare L-glutamic acid/amylose modified glassy carbon electrode: immersed in 20 ~ 30mL amylose solution by the L-glutamic acid modified glassy carbon electrode of preparation, self assembly 18 ~ 28h at 8 DEG C, obtains L-glutamic acid/amylose modified glassy carbon electrode.
The Selective recognition of c, tryptophan enantiomorph: adopt differential pulse method to identify Tryptophan enantiomer, L-glutamic acid/amylose modified glassy carbon electrode is rested in the 20 ~ 30mL Tryptophan enantiomer solution under different temperatures (2 ~ 42 DEG C) (time of repose 30 ~ 90s), within the scope of the electrochemical window of 0.4 ~ 1.0V (vs.SCE), differential pulse is carried out with the speed of sweeping of 0.1 ~ 0.5V/s, the complete rear modified electrode of each survey is swept and is surely recovered electrode activity in 20 ~ 30mL blank solution (0.1 ~ 0.3M sodium dihydrogen phosphate, pH=6 ~ 7).
Further, in step a, the concentration of Pidolidone is 0.03 ~ 0.06M.
Further, in step b, the concentration of amylose is 1 ~ 3mg/mL.
Further, in step c, the concentration of Tryptophan enantiomer is 0.2 ~ 1mM.
The invention has the beneficial effects as follows: the preparation method of L-glutamic acid/amylose modified glassy carbon electrode is simple, convenient, pollution-free, this modified electrode tryptophan enantiomorph has good recognition effect.This is owing to the stereoselectivity of amylose tryptophan enantiomorph.
Accompanying drawing explanation
Below in conjunction with accompanying drawing, this experiment is further illustrated.
Fig. 1 is the cyclic voltammogram of different modifying electrode in embodiment one; A in Fig. 1: glass-carbon electrode, b: L-glutamic acid modified glassy carbon electrode, c: L-glutamic acid/amylose modified glassy carbon electrode.
Fig. 2 is L-glutamic acid modified glassy carbon electrode (a) and the cyclic voltammogram of L-glutamic acid/amylose modified glassy carbon electrode prepared at different temperatures in embodiment two; B:4 DEG C, c:8 DEG C, d:12 DEG C, e:20 DEG C.
Fig. 3 be in embodiment three the different self assembly time on identify impact.
Fig. 4 be in embodiment four temperature on identify impact.
Fig. 5 is the histogram of four kinds of different modifying electrode pair Tryptophan enantiomer oxidation peak current ratios in comparative example one, A: glass-carbon electrode, B: L-glutamic acid modified glassy carbon electrode, C: amylose modified glassy carbon electrode, D: L-glutamic acid/amylose modified glassy carbon electrode.
Embodiment
The invention will be further described in conjunction with specific embodiments now, and following examples are intended to the present invention instead of limitation of the invention further are described.
Embodiment one:
(1) 2mg/mL amylose solution (solvent is ultrapure water) is prepared.
(2) (solvent is 0.1M sodium dihydrogen phosphate to prepare 0.05mML-glutamic acid solution, pH=7), adopt cyclic voltammetry that Pidolidone is deposited on glassy carbon electrode surface, potential range is-0.6 ~ 2.0V, sweep speed for 0.1V/s, the scanning number of turns is 20 circles, obtains L-glutamic acid modified glassy carbon electrode.
(3) L-glutamic acid modified glassy carbon electrode step 2 prepared rests on self assembly 24h in the solution that step 1 prepares at 8 DEG C, obtains L-glutamic acid/amylose modified glassy carbon electrode.
(4) rest in 5mM potassium ferricyanide solution by the electrode that step 2,3 prepares, adopt cyclic voltammetry to characterize, potential range is-0.2 ~ 0.6V, and sweep speed for 0.1V/s, the scanning number of turns is 20 circles, and its result as shown in Figure 1.
Embodiment two:
In order to investigate the difference of L-glutamic acid/amylose modified glassy carbon electrode tryptophan recognition capability prepared by different self assembly temperature.Therefore, the time of self assembly adopts 4 DEG C, 8 DEG C, 12 DEG C and 20 DEG C respectively.It the results are shown in Figure 2, and visible when the temperature of self assembly is 8 DEG C, the electric current of its cyclic voltammogram is minimum, and this is caused by the weak electric conductivity of amylose.Visible, the amount that when temperature of self assembly is 8 DEG C, amylose is loaded into above electrode is maximum.
Embodiment three:
In order to investigate the difference of L-glutamic acid/amylose modified glassy carbon electrode tryptophan recognition capability prepared by the different self assembly time.Therefore, the time of self assembly adopts 8h, 12h, 15h, 18h, 20h, 22h, 24h and 26h respectively.It the results are shown in Figure 3, and visible when the time of self assembly is 24h, the oxidation peak current ratio of L-/D-tryptophane reaches maximum, and time shorter when self assembled, the amount that amylose self-assembles on electrode is little, causes recognition capability lower.Along with the increase of self assembly time, the amount that amylose self-assembles on electrode increases gradually, and when the time of self assembly is 24h, amylose self assembly amount reaches capacity, and effectively can identify Tryptophan enantiomer.But along with the self assembly time continues to increase, amylose self assembly amount is too much, and too much amylose causes the breakage of poly-L-glutamic acid sorrel, thus is unfavorable for identifying.
Embodiment four:
In order to investigate the difference of L-glutamic acid/amylose modified glassy carbon electrode tryptophan recognition capability at different temperature.Therefore, 2 DEG C, 4 DEG C, 8 DEG C, 12 DEG C, 15 DEG C, 20 DEG C, 25 DEG C, 30 DEG C, 35 DEG C, 37 DEG C and 42 DEG C are adopted respectively.It the results are shown in Figure 4, and visible when temperature is 37 DEG C, the oxidation peak current ratio of L-/D-tryptophane reaches maximum.When 4 DEG C, due to hydrone self-interaction, thus limit its motion, the hydrogen bond that this system main water is formed mutually is main, suppresses the formation of hydrogen bond between amylose and tryptophane, causes this system recognition efficiency lower.When raising along with temperature, hydrone interacts and weakens gradually, and cause the hydrogen bond between hydrone to start gradually to destroy, the formation gradually of hydrogen bond between hydrone and D-trp, recognition efficiency raises gradually.Compared with L-Trp, when 8 DEG C, form stable single hydrogen bond between hydrone and D-trp, the more difficult amylose helical structure that penetrates of D-trp arrives electrode surface, therefore obtains higher recognition effect.When continuing along with temperature to be increased to 37 DEG C, reach the highest recognition effect, this is owing to forming stable dihydrogen bond between hydrone and D-trp.But along with temperature continues to raise, stable dihydrogen bond is damaged, and causes host-guest interaction to weaken, and recognition efficiency declines.
Comparative example one:
Prepare glass-carbon electrode, L-glutamic acid modified glassy carbon electrode, amylose modified glassy carbon electrode and L-glutamic acid/amylose modified glassy carbon electrode, compare the recognition capability of these four kinds of electrode pair Tryptophan enantiomer.
It the results are shown in Figure 5, can find out, glass-carbon electrode and L-glutamic acid modified glassy carbon electrode tryptophan enantiomorph almost do not have recognition effect.The oxidation peak current ratio of amylose modified glassy carbon electrode tryptophan enantiomorph is 1.42, and this may be that the amount be adsorbed on glass-carbon electrode due to amylose is less, causes recognition effect lower.But this problem can by modifying Pidolidone and being resolved on glass-carbon electrode.The oxidation peak current ratio of L-glutamic acid/amylose modified glassy carbon electrode tryptophan enantiomorph reaches 2.67.Compared with amylose-D-trp, amylose-L-Trp has higher electric current, and this illustrates that the helical structure having more L-Trp to penetrate amylose arrives electrode surface.The lower electric current of amylose-D-trp illustrates when the indolyl radical of tryptophane enters the helical structure of amylose, compared with L-Trp, due to less sterically hindered of D-trp, and-the NH on D-trp
2stable hydrogen bond can be formed with the water of crystallization in amylose, make it more be conducive to the inclusion of D-trp.Just because of this, the more difficult helical structure penetrating amylose of D-trp arrives electrode surface, causes lower electric current.The order of each modified electrode electrochemical recognition Tryptophan enantiomer is: L-glutamic acid/amylose modified glassy carbon electrode > amylose modified glassy carbon electrode > L-glutamic acid modified glassy carbon electrode ≈ glass-carbon electrode.
The present invention has prepared the Selective recognition of L-glutamic acid/amylose modified glassy carbon electrode tryptophan enantiomorph.Result shows, is 0.5mM in the concentration of Tryptophan enantiomer, and the self assembly time is 24h, and self assembly temperature is 8 DEG C, and identify that temperature is under the condition of 37 DEG C, recognition efficiency reaches maximum.
Claims (4)
1., based on the Selective recognition of L-glutamic acid/amylose modified glassy carbon electrode tryptophan enantiomorph, step is as follows:
A, prepare L-glutamic acid modified glassy carbon electrode: preparation Pidolidone solution (solvent is 0.1 ~ 0.3M sodium dihydrogen phosphate, pH=6 ~ 7), adopt cyclic voltammetry to be deposited on glassy carbon electrode surface, obtain L-glutamic acid modified glassy carbon electrode.
B, prepare L-glutamic acid/amylose modified glassy carbon electrode: immersed in 20 ~ 30mL amylose solution by the L-glutamic acid modified glassy carbon electrode of preparation, self assembly 18 ~ 28h at 8 DEG C, obtains L-glutamic acid/amylose modified glassy carbon electrode.
The Selective recognition of c, tryptophan enantiomorph: adopt differential pulse method to identify Tryptophan enantiomer, L-glutamic acid/amylose modified glassy carbon electrode is rested in the 20 ~ 30mL Tryptophan enantiomer solution under different temperatures (2 ~ 42 DEG C) (time of repose 30 ~ 90s), within the scope of the electrochemical window of 0.4 ~ 1.0V (vs.SCE), differential pulse is carried out with the speed of sweeping of 0.1 ~ 0.5V/s, the complete rear modified electrode of each survey is swept and is surely recovered electrode activity in 20 ~ 30mL blank solution (0.1 ~ 0.3M sodium dihydrogen phosphate, pH=6 ~ 7).
2., according to claim 1 based on the Selective recognition of L-glutamic acid/amylose modified glassy carbon electrode tryptophan enantiomorph, it is characterized in that: in described step a, the concentration of Pidolidone is 0.03 ~ 0.06M.
3., according to claim 1 based on the Selective recognition of L-glutamic acid/amylose modified glassy carbon electrode tryptophan enantiomorph, it is characterized in that: in described step b, the concentration of amylose is 1 ~ 3mg/mL.
4., according to claim 1 based on the Selective recognition of L-glutamic acid/amylose modified glassy carbon electrode tryptophan enantiomorph, it is characterized in that: in described step c, the concentration of Tryptophan enantiomer is 0.2 ~ 1mM.
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| CN106053584A (en) * | 2016-07-29 | 2016-10-26 | 广西师范学院 | Method for detecting concentration of asparagines in solution |
| CN106226381A (en) * | 2016-07-11 | 2016-12-14 | 常州大学 | The preparation of a kind of Thermo-sensitive quinine chiral sensor and be applied to electrochemical recognition Tryptophan enantiomer |
| CN106290536A (en) * | 2016-07-29 | 2017-01-04 | 广西师范学院 | The method of aspartic acid concentration in detection solution |
| 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 |
| CN108844982A (en) * | 2018-06-26 | 2018-11-20 | 常州大学 | A method of Tryptophan enantiomer is identified based on ternary self-assembly system |
| CN116574414A (en) * | 2023-05-16 | 2023-08-11 | 内江师范学院 | Graphite powder/starch chiral selector, glassy carbon electrode, preparation method and application |
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| 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 |
| CN108844982A (en) * | 2018-06-26 | 2018-11-20 | 常州大学 | A method of Tryptophan enantiomer is identified based on ternary self-assembly system |
| CN108844982B (en) * | 2018-06-26 | 2021-01-29 | 常州大学 | Method for identifying tryptophan enantiomer based on ternary self-assembly system |
| CN116574414A (en) * | 2023-05-16 | 2023-08-11 | 内江师范学院 | Graphite powder/starch chiral selector, glassy carbon electrode, preparation method and application |
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