CN110455880B - Preparation method of L-lysine hydrochloride induced tetra-p-carboxyphenylporphyrin self-assembly for electrochemical chiral recognition - Google Patents
Preparation method of L-lysine hydrochloride induced tetra-p-carboxyphenylporphyrin self-assembly for electrochemical chiral recognition Download PDFInfo
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- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 title claims abstract description 77
- 238000001338 self-assembly Methods 0.000 title claims abstract description 40
- 238000005557 chiral recognition Methods 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical class C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims abstract description 27
- RCEXBQFQNWFTDN-UHFFFAOYSA-N N1C2=CC([N]3)=CC=C3C=C(N3)C=CC3=CC([N]3)=CC=C3C=C1C(C(=O)O)=C2C1=CC=CC=C1 Chemical compound N1C2=CC([N]3)=CC=C3C=C(N3)C=CC3=CC([N]3)=CC=C3C=C1C(C(=O)O)=C2C1=CC=CC=C1 RCEXBQFQNWFTDN-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 13
- 238000002848 electrochemical method Methods 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 16
- 238000001318 differential pulse voltammogram Methods 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 238000012546 transfer Methods 0.000 claims description 7
- 229930182827 D-tryptophan Natural products 0.000 claims description 6
- 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 6
- 229910021397 glassy carbon Inorganic materials 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 229910021642 ultra pure water Inorganic materials 0.000 claims description 6
- 239000012498 ultrapure water Substances 0.000 claims description 6
- 238000005259 measurement Methods 0.000 claims description 4
- 239000008055 phosphate buffer solution Substances 0.000 claims description 4
- 238000010408 sweeping Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 238000005303 weighing Methods 0.000 claims description 3
- 230000001939 inductive effect Effects 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 235000001014 amino acid Nutrition 0.000 description 9
- 150000001413 amino acids Chemical class 0.000 description 8
- 239000002608 ionic liquid Substances 0.000 description 7
- -1 amino acid enantiomers Chemical class 0.000 description 6
- 150000004032 porphyrins Chemical class 0.000 description 5
- 229960004799 tryptophan Drugs 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001000 micrograph Methods 0.000 description 4
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 3
- 238000002484 cyclic voltammetry Methods 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000004472 Lysine Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 229960003646 lysine Drugs 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 235000019766 L-Lysine Nutrition 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000003487 electrochemical reaction Methods 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 235000018977 lysine Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004033 porphyrin derivatives Chemical class 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
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Abstract
The invention relates to a preparation method of L-lysine hydrochloride induced tetra-p-carboxyl phenyl porphyrin self-assembly for electrochemical chiral recognition. The method comprises the following steps: preparing L-lysine hydrochloride induced four pairs of carboxyl phenyl porphyrin solution, preparing an L-lysine hydrochloride induced four pairs of carboxyl phenyl porphyrin self-assembly modified electrode, and identifying tryptophan enantiomer by an electrochemical method. The invention has the beneficial effects that: the preparation method of the L-lysine hydrochloride induced tetra-p-carboxyphenylporphyrin self-assembly is simple and environment-friendly, and the L-lysine hydrochloride has a chiral environment, so that the L-lysine hydrochloride induced tetra-p-carboxyphenylporphyrin self-assembly modified electrode has good identification capability on tryptophan enantiomers.
Description
Technical Field
The invention relates to a preparation method of L-lysine hydrochloride induced tetra-p-carboxyphenylporphyrin self-assembly for electrochemical chiral recognition, belonging to the fields of biotechnology and electrochemistry.
Technical Field
Chiral and chiral analysis are of great interest in modern chemistry and chemical technology, and the development of simple and intelligent enantioselective assay devices has become a focus of research in life sciences and many other related fields. Amino acids are molecular structural units of living bodies and play a crucial role in many related fields such as life systems. However, amino acids are important enantiomeric compounds, the different configurations of which play different and even opposite roles in life sciences. Therefore, chiral recognition of the enantiomers of amino acids is of great significance in life sciences. At present, the most common methods for enantioselective separation are mainly chromatography and spectroscopy, however, both methods are costly and time consuming. In recent years, work has been reported by our team on electrochemical chiral recognition of amino acid enantiomers using natural polysaccharides. However, to our knowledge, little progress has been made in electrochemical chiral recognition using biological units such as amino acids, peptides and proteins.
The ionic liquid is a novel liquid material with great potential, has the characteristics of excellent dissolving capacity, excellent electric conductivity, good electrochemical performance, stable thermochemical performance and the like, and is widely used as a medium in various fields, such as a solvent for chemical reaction, an electrolyte solution for electrochemical reaction, a biochemical separation extractant and the like. L-lysine hydrochloride belongs to one of amino acid ionic liquids, and is chiral ionic liquid prepared by taking natural chiral lysine as a chiral source and interacting with other anions and cations. The amino acid ionic liquid has a series of advantages of common ionic liquid, and also has a natural chiral center, so that the amino acid ionic liquid can be used for chiral recognition.
Porphyrins are well known building blocks with heterocyclic macrocycles and large pi-pi conjugated systems that have been widely used in catalysis, photovoltaic devices, and chemical sensors. Porphyrin derivatives are various in types, and not only have the electrochemical and photochemical properties of porphyrin, but also have quite interesting molecular recognition phenomena. The tetra-p-carboxyl phenyl porphyrin contains four carboxyl groups, and can be combined with the amino acid ionic liquid to form a self-assembly body, so that isomer guest molecules can be effectively identified. The L-lysine hydrochloride and porphyrin are utilized to form a self-assembly, simultaneously, chiral characteristics are endowed to achiral porphyrin, the conductivity of the achiral porphyrin is increased, and the self-assembly is used for electrochemical chiral recognition of tryptophan enantiomers.
Disclosure of Invention
The invention aims to provide a preparation method of an L-lysine hydrochloride induced tetra-p-carboxyphenylporphyrin self-assembly for electrochemical chiral recognition. After the L-lysine hydrochloride induced four-pair carboxyl phenyl porphyrin self-assembly is modified on a glassy carbon electrode, the tryptophan enantiomer can be effectively identified.
A preparation method of L-lysine hydrochloride induced tetra-p-carboxyphenylporphyrin self-assembly for electrochemical chiral recognition comprises the following steps:
a. preparing an L-lysine hydrochloride induced tetra-p-carboxyphenylporphyrin solution: weighing a certain amount of tetra-p-carboxyphenylporphyrin and L-lysine hydrochloride in a beaker, adding N, N-dimethylformamide, heating and stirring to dissolve the tetra-p-carboxyphenylporphyrin and the L-lysine hydrochloride to transparent purple, adding a certain amount of ultrapure water into the purple solution, cooling to room temperature, and enabling the purple transparent solution to become an opaque suspension, namely obtaining an L-lysine hydrochloride induced tetra-p-carboxyphenylporphyrin solution;
b. preparing an L-lysine hydrochloride induced four-p-carboxyl phenyl porphyrin self-assembly modified electrode: b, transferring the L-lysine hydrochloride induced four pairs of carboxyl phenyl porphyrin solution prepared in the step a by using a liquid transfer gun, dripping the L-lysine hydrochloride induced four pairs of carboxyl phenyl porphyrin solution on the surface of a glassy carbon electrode, and incubating for a certain time at a certain temperature to obtain an L-lysine hydrochloride induced four pairs of carboxyl phenyl porphyrin self-assembly modified electrode;
c. identification of tryptophan enantiomers by electrochemical methods: identifying a tryptophan enantiomer by adopting a differential pulse method, standing an L-lysine hydrochloride induced four-pair carboxyl phenyl porphyrin self-assembly modified electrode in 20-30 mL-tryptophan and D-tryptophan solutions for a certain time, recording a differential pulse voltammogram within an electrochemical window range of 0.4-1.2V, and after each measurement, sweeping the modified electrode in 20-30 mL of 0.1-0.3M phosphate buffer solution with the pH value of 6-8 to restore the electrode activity.
Furthermore, in the step a, the mass of the tetra-p-carboxyphenylporphyrin, the mass of the L-lysine hydrochloride, the volume of the N, N-dimethylformamide and the volume of the ultrapure water are respectively 0.4-0.6 mg, 10-15 mg, 300-400 mu L and 100-200 mu L, respectively.
Further, the volume of the L-lysine hydrochloride induced tetra-p-carboxyphenylporphyrin solution transferred by the liquid transfer gun in the step b is 1-10 mu L, the incubation temperature is 20-40 ℃, and the incubation time is 2-4 h.
Furthermore, the concentration of the L-tryptophan and the concentration of the D-tryptophan in the step c are both 0.1-1 mM, and the standing time is 30-90 s.
The invention has the beneficial effects that: the preparation method of the L-lysine hydrochloride induced tetra-p-carboxyphenylporphyrin self-assembly is simple and environment-friendly, and the L-lysine hydrochloride has a chiral environment, so that the L-lysine hydrochloride induced tetra-p-carboxyphenylporphyrin self-assembly modified electrode has good identification capability on tryptophan enantiomers.
Drawings
The experiment is further described below with reference to the accompanying drawings.
FIG. 1 is a scanning electron microscope image of field emission of an L-lysine hydrochloride-induced tetra-p-carboxyphenylporphyrin self-assembly modified electrode in example I.
FIG. 2 is a cyclic voltammogram of L-lysine hydrochloride-induced tetra-p-carboxyphenylporphyrin self-assembly modified electrode in example II and L-lysine hydrochloride modified electrode in comparative example I in a 5mM potassium ferricyanide solution.
FIG. 3 is a differential pulse voltammogram of L-lysine hydrochloride induced four pairs of carboxyphenylporphyrin autoporphyrin modified electrodes of example III against the 0.5mM tryptophan enantiomer in 0.1M phosphate buffer at pH 7.
FIG. 4 is a bar graph showing the effect of L-lysine hydrochloride-induced self-assembly modified electrode of tetra-p-carboxyphenylporphyrin in example III and the effect of L-lysine hydrochloride-modified electrode in comparative example I on the recognition of 0.5mM tryptophan enantiomer in 0.1M phosphate buffer at pH 7.
FIG. 5 is a scanning electron microscope image of the L-lysine hydrochloride modified electrode in comparative example I.
Detailed Description
The invention will now be further illustrated by reference to specific examples, which are intended to be illustrative of the invention and are not intended to be a further limitation of the invention.
The L-lysine hydrochloride induced four-pair carboxyl phenyl porphyrin self-assembly modified electrode identifies the tryptophan enantiomer according to the following method:
RL/D＝IL/ID
in the formula, RL/DRepresents the oxidation peak current ratio of tryptophan enantiomer, ILAnd IDThe oxidation peak current values of L-tryptophan and D-tryptophan on the differential pulse voltammogram are shown, respectively.
The first embodiment is as follows:
the preparation of the L-lysine hydrochloride induced tetra-p-carboxyl phenyl porphyrin self-assembly modified electrode comprises the following steps:
(1) 0.5mg of tetra-p-carboxyphenylporphyrin and 12.5mg of L-lysine hydrochloride are weighed in a beaker, 350 mu L N of N-dimethylformamide is added immediately, the mixture is heated and stirred to be dissolved to be transparent purple, 150 mu L of ultrapure water is added into the prepared solution dropwise, the solution is cooled to room temperature, the transparent solution becomes opaque suspension, and the L-lysine hydrochloride induced tetra-p-carboxyphenylporphyrin solution is obtained.
(2) And (2) transferring the L-lysine hydrochloride induced four pairs of carboxyl phenyl porphyrin solution prepared in the step (1) by using a liquid transfer gun, dripping the solution on the surface of a glassy carbon electrode, and incubating for 3 hours at the temperature of 30 ℃ to obtain the L-lysine hydrochloride induced four pairs of carboxyl phenyl porphyrin self-assembly modified electrode.
FIG. 1 is a field emission scanning electron microscope image of an L-lysine hydrochloride induced four-pair carboxyl phenyl porphyrin self-assembly modified electrode, and the L-lysine hydrochloride induced four-pair carboxyl phenyl porphyrin self-assembly modified electrode is in a porous shape formed by densely stacking irregular slices from the attached FIG. 1.
Example two:
standing the L-lysine hydrochloride induced four-pair carboxyphenylporphyrin self-assembly modified electrode and the single L-lysine hydrochloride modified electrode prepared in the first embodiment in a 5mM potassium ferricyanide solution, and characterizing the modified electrodes by adopting a cyclic voltammetry method under an electrochemical window of-0.2-0.6V, wherein the sweep rate is 0.1V/s, the number of scanning turns is 20, and the result is shown in figure 2, and the L-lysine hydrochloride induced four-pair carboxyphenylporphyrin self-assembly modified electrode and the single L-lysine hydrochloride modified electrode are shown in a reversible symmetrical cyclic voltammogram. It can be seen from the figure that L-lysine hydrochloride induces a significant reduction in the current of the tetra-p-carboxyphenylporphyrin self-assembly modified electrode compared to the L-lysine hydrochloride modified electrode, because the weak conductivity of the tetra-p-carboxyphenylporphyrin hinders the charge transfer of the ferricyanate ion/ferricyanate ion pair.
Example three:
the L-lysine hydrochloride induced four-p-carboxyphenylporphyrin self-assembly modified electrode prepared in the first embodiment is respectively placed in 25mL of 0.5mM L-tryptophan solution and D-tryptophan solution, a differential pulse voltammogram is recorded in an electrochemical window range of 0.4-1.2V after the L-lysine hydrochloride induced four-p-carboxyphenylporphyrin self-assembly modified electrode is placed for 60s, and after each measurement, the modified electrode is subjected to stable sweeping in 25mL of 0.1M phosphate buffer solution with the pH value of 7 to restore the electrode activity. Tryptophan enantiomer on L-lysine hydrochloride induced tetra-p-carboxyphenylporphyrin self-assembly modified electrodeThe differential pulse voltammogram is shown in figure 3, and the L-lysine hydrochloride induced four pairs of carboxyl phenyl porphyrin self-assembly modified electrode has good identification effect on tryptophan enantiomer (R)L/DIs 4.63).
Comparative example one:
the identification of the tryptophan enantiomer by the L-lysine hydrochloride modified electrode comprises the following steps:
(1) weighing 12.5mg L-lysine hydrochloride in a beaker, immediately adding 350 mu L N, N-dimethylformamide, heating and stirring to dissolve, dripping 150 mu L ultrapure water into the prepared solution, and cooling to room temperature to obtain L-lysine hydrochloride solution;
(2) transferring 5 mu L of the L-lysine hydrochloride solution prepared in the step (1) by using a liquid transfer gun, dripping the solution on the surface of a glassy carbon electrode, and incubating the glassy carbon electrode at the temperature of 30 ℃ for 3 hours to obtain an L-lysine hydrochloride modified electrode;
(3) and (3) respectively standing the L-lysine hydrochloride modified electrode prepared in the step (2) in 25mL of 0.5mM L-tryptophan solution and D-tryptophan solution, recording a differential pulse voltammogram within an electrochemical window range of 0.4-1.2V after standing for 60s, and after each measurement, sweeping the modified electrode in 25mL of 0.1M phosphate buffer solution with the pH value of 7 to restore the electrode activity. As shown in figure 4, the oxidation peak current ratio of the L-lysine hydrochloride modified electrode to the tryptophan enantiomer is only 1.34, because the L-lysine hydrochloride is densely packed on the surface of the modified electrode, so that holes are sparse, and the contact between tryptophan isomer molecules and chiral sites of the L-lysine hydrochloride is not facilitated. The field emission scanning electron microscope image of the L-lysine hydrochloride modified electrode is shown in figure 5.
Claims (4)
1. A preparation method of L-lysine hydrochloride induced tetra-p-carboxyphenylporphyrin self-assembly for electrochemical chiral recognition comprises the following steps:
a. preparing an L-lysine hydrochloride induced tetra-p-carboxyphenylporphyrin solution: weighing a certain amount of tetra-p-carboxyphenylporphyrin and L-lysine hydrochloride in a beaker, adding N, N-dimethylformamide, heating and stirring to dissolve the tetra-p-carboxyphenylporphyrin and the L-lysine hydrochloride to be transparent purple, dripping a certain amount of ultrapure water into the prepared solution, cooling to room temperature, and enabling the purple transparent solution to become an opaque suspension to obtain an L-lysine hydrochloride induced tetra-p-carboxyphenylporphyrin solution;
b. preparing an L-lysine hydrochloride induced four-p-carboxyl phenyl porphyrin self-assembly modified electrode: b, transferring the L-lysine hydrochloride induced four pairs of carboxyl phenyl porphyrin solution prepared in the step a by using a liquid transfer gun, dripping the L-lysine hydrochloride induced four pairs of carboxyl phenyl porphyrin solution on the surface of a glassy carbon electrode, and incubating for a certain time at a certain temperature to obtain an L-lysine hydrochloride induced four pairs of carboxyl phenyl porphyrin self-assembly modified electrode;
c. identification of tryptophan enantiomers by electrochemical methods: identifying a tryptophan enantiomer by adopting a differential pulse method, standing an L-lysine hydrochloride induced four-pair carboxyl phenyl porphyrin self-assembly modified electrode in 20-30 mL-tryptophan and D-tryptophan solutions for a certain time, recording a differential pulse voltammogram within an electrochemical window range of 0.4-1.2V, and after each measurement, stably sweeping the modified electrode in 20-30 mL of 0.1-0.3M phosphate buffer solution with the pH value of 6-8 to restore the electrode activity.
2. The method for preparing L-lysine hydrochloride-induced tetra-p-carboxyphenylporphyrin self-assembly for electrochemical chiral recognition according to claim 1, wherein the method comprises the following steps: in the step a, the mass of the L-lysine hydrochloride is 10-15 mg, the mass of the tetra-p-carboxyphenylporphyrin is 0.4-0.6 mg, the volume of the N, N-dimethylformamide is 300-400 mu L, and the volume of the ultrapure water is 100-200 mu L.
3. The method for preparing L-lysine hydrochloride-induced tetra-p-carboxyphenylporphyrin self-assembly for electrochemical chiral recognition according to claim 1, wherein the method comprises the following steps: and (b) inducing the volume of the tetra-p-carboxyphenylporphyrin by the L-lysine hydrochloride transferred by the liquid transfer gun in the step (b) to be 1-10 mu L, incubating at the temperature of 20-40 ℃ for 2-4 h.
4. The method for preparing L-lysine hydrochloride-induced tetra-p-carboxyphenylporphyrin self-assembly for electrochemical chiral recognition according to claim 1, wherein the method comprises the following steps: in the step c, the concentration of the tryptophan enantiomer is 0.1-1 mM, and the standing time is 30-90 s.
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| CN104629073A (en) * | 2014-12-17 | 2015-05-20 | 天津工业大学 | Amino acid induced supramolecular chiral membrane and preparation method thereof |
| 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 |
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| CN104629073A (en) * | 2014-12-17 | 2015-05-20 | 天津工业大学 | Amino acid induced supramolecular chiral membrane and preparation method thereof |
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