CN114755193A - Chiral carbon point-based colorimetric detection method for identifying glutamic acid enantiomer - Google Patents
Chiral carbon point-based colorimetric detection method for identifying glutamic acid enantiomer Download PDFInfo
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 title claims abstract description 8
- 238000001514 detection method Methods 0.000 title claims abstract description 6
- 238000000357 thermal conductivity detection Methods 0.000 claims abstract description 39
- 238000002835 absorbance Methods 0.000 claims abstract description 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 12
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 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 claims abstract description 8
- 230000009471 action Effects 0.000 claims abstract description 7
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 6
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 6
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-Glutamic acid Natural products OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 45
- 229960002989 glutamic acid Drugs 0.000 claims description 23
- WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical class OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 claims description 20
- 229930182847 D-glutamic acid Natural products 0.000 claims description 13
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 claims description 9
- 230000008859 change Effects 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 5
- 238000005557 chiral recognition Methods 0.000 claims description 3
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 238000000862 absorption spectrum Methods 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 235000001014 amino acid Nutrition 0.000 abstract description 11
- 150000001413 amino acids Chemical class 0.000 abstract description 8
- 238000002371 ultraviolet--visible spectrum Methods 0.000 abstract description 7
- 239000000523 sample Substances 0.000 abstract description 3
- 238000010183 spectrum analysis Methods 0.000 abstract description 2
- 238000005530 etching Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 36
- 229940024606 amino acid Drugs 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 5
- 235000013922 glutamic acid Nutrition 0.000 description 5
- 239000004220 glutamic acid Substances 0.000 description 5
- 239000000872 buffer Substances 0.000 description 4
- 238000004737 colorimetric analysis Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- -1 amino acid enantiomers Chemical class 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- IWRJMQUPCKSBFP-UHFFFAOYSA-N 2-n-methylbenzene-1,2-diamine;hydrochloride Chemical compound Cl.CNC1=CC=CC=C1N IWRJMQUPCKSBFP-UHFFFAOYSA-N 0.000 description 2
- 238000003917 TEM image Methods 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 238000001142 circular dichroism spectrum Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 description 2
- 235000013923 monosodium glutamate Nutrition 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960004799 tryptophan Drugs 0.000 description 2
- 229910021642 ultra pure water Inorganic materials 0.000 description 2
- 239000012498 ultrapure water Substances 0.000 description 2
- 206010010075 Coma hepatic Diseases 0.000 description 1
- 150000008575 L-amino acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005251 capillar electrophoresis Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 201000001059 hepatic coma Diseases 0.000 description 1
- 208000007386 hepatic encephalopathy Diseases 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000006371 metabolic abnormality Effects 0.000 description 1
- 239000004223 monosodium glutamate Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 229940073490 sodium glutamate Drugs 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
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Abstract
The invention provides a colorimetric detection method for identifying a glutamic acid enantiomer by utilizing a chiral carbon point, belonging to the field of spectral analysis and chiral identification. The invention synthesizes chiral carbon dots (L-TCDs) which are used as colorimetric probes, and can show excellent enantioselective colorimetric response and absorbance signal difference on glutamic acid enantiomers under the action of hydrogen peroxide, and the maximum difference ratio of the signal values of the enantiomers can reach 8.16. The chiral colorimetric identification of the glutamic acid enantiomer is realized according to the difference of ultraviolet-visible spectrum signals of the L-TCDs and the difference of the oxidation etching degree of the L-TCDs caused by the binding force difference between the L-TCDs and the glutamic acid enantiomer of the hydrogen peroxide. The invention can conveniently and rapidly carry out chiral identification, can directly distinguish glutamic acid enantiomers by naked eyes, has the advantages of low cost, easy material synthesis, simple operation and the like, and has certain application prospect in the aspects of chiral distinction, purity identification and the like of chiral amino acid.
Description
Technical Field
The invention relates to the technical field of chiral carbon dots, in particular to the fields of spectral analysis and chiral recognition of glutamic acid enantiomers.
Background
Chirality refers to the phenomenon that an object cannot coincide with its mirror image, and the phenomenon of chirality also exists widely in nature, and chirality is a basic attribute of nature. In general, enantiomers, although having similar physicochemical properties, in most cases, exhibit entirely different and even opposite biochemical or pharmacological effects. Chiral-dependent interactions and physiological events also occur in humans, since only L-amino acids are present in humans. Many chiral amino acids used as medicines also have pharmacological action, and enantiomers of amino acids also show different pharmacological actions, often D-type amino acids easily show metabolic abnormality or physiological toxicity, such as L-glutamic acid has wide application, and the D-type amino acids used as medicines can treat hepatic coma, and can also be used for producing monosodium glutamate (sodium glutamate), food additives, spices and for biochemical research; d-glutamic acid has a narrow application range and is commonly used in biochemical research and amino acid drugs.
At present, chromatography is mainly used for distinguishing the amino acid enantiomers, and high performance liquid chromatography, gas chromatography, capillary electrophoresis and the like are commonly used, but the methods are still to be improved in aspects of expensive instruments, complex operation and the like, so that the development of a method which is low in cost, simple to operate and capable of quickly detecting and distinguishing the amino acid enantiomers is of great significance. The colorimetric method has the advantages of simplicity, low cost, practicality, convenience and capability of being directly observed by naked eyes, the Au/Ag nano particles are usually applied to colorimetric identification of chiral amino acid at present, but the Au/Ag nano particles have the defects of high cost, complex synthetic steps and the like, and Carbon Dots (CDs) have the advantages of low toxicity, easiness in synthesis, low cost and the like, so that if the colorimetric method for chiral identification of amino acid enantiomers based on the carbon dots can be invented, the colorimetric method has important practical application value.
Disclosure of Invention
Based on the above problems, the present invention aims to provide a colorimetric detection method capable of rapidly identifying the enantiomers of glutamic acid, and the invention also includes a method for synthesizing chiral carbon dots (L-TCDs) as a probe used in the method.
In order to achieve the purpose, the invention adopts the following technical scheme:
the synthesis method of the L-TCDs comprises the following steps:
1. mixing N-methyl o-phenylenediamine hydrochloride (OTD) and L-tryptophan (L-Trp) according to a mass ratio of 1: 1.25 dissolving in ultrapure water, and then adding concentrated sulfuric acid, wherein the volume ratio of the concentrated sulfuric acid to the ultrapure water is 1: 20;
2. uniformly mixing the solutions, transferring the mixed solution into a reaction kettle, and heating the mixed solution for 8 hours at 160 ℃;
3. after the reaction is finished, after the reaction kettle is cooled to room temperature, centrifuging the carbon point solution and collecting supernatant to obtain the L-TCDs solution.
The application of L-TCDs in the colorimetric identification of glutamic acid enantiomers:
1. dispersing appropriate amount of L-TCDs solution in Tris-HCl (pH 7.40), and adding appropriate amount of hydrogen peroxide (H)2O2) Then adding an L-glutamic acid (L-Glu) solution, and reacting for a period of time at a certain temperature to change the color of the solution from light blue to yellow;
2. dispersing appropriate amount of L-TCDs solution in Tris-HCl (pH 7.40), and adding appropriate amount of hydrogen peroxide (H) 2O2) Then adding D-glutamic acid (D-Glu) solution, and reacting for a period of time at a certain temperature to keep the color of the solution unchanged.
The advantages and the beneficial effects of the invention are as follows:
the invention develops a simple, convenient, rapid and low-cost chiral identification method for glutamic acid based on chiral carbon dots (L-TCDs). The chiral carbon dots are used as probes, and have the advantages of easy synthesis, low cost and the like. Can realize chiral recognition of the glutamic acid enantiomer by a simple colorimetric method, and is a method for rapidly and visually recognizing the glutamic acid enantiomer by chirality
Drawings
FIG. 1 is a transmission electron micrograph of the synthesized L-TCDs
FIG. 2 circular dichroism spectra of synthesized L-TCDs
FIG. 3 Gray scale conversion chart of color change after L-TCDs react with L-Glu of different concentrations
FIG. 4 Gray scale conversion chart of color change after interaction of L-TCDs with D-Glu of different concentrations
FIG. 5 UV-VISIBLE SPECTRUM OF L-TCDs ACTION WITH L-Glu AT VARIOUS CONCENTRATION
FIG. 6 UV-VISIBLE SPECTRUM GENERATED BY L-TCDs ACTION WITH D-Glu AT VARIABLE CONCENTRATION
FIG. 7 ratio of absorbance signals (A) after the effect of L-TCDs and various concentrations of glutamic acid enantiomers461/A618) The color of the solution is shown by the gray color of the solution after 10mM L and D-Glu are added to the L-TCDs system Degree conversion chart
FIG. 8 ratio of absorbance signals (A) after the action of L-TCDs and different concentrations of L-Glu461/A618) Linear relationship with L-Glu concentration
FIG. 9 Gray scale transition plot of color change after Effect of enantiomeric excess of L-TCDs and different L-Glus FIG. 10 ultraviolet-visible spectra after Effect of enantiomeric excess of L-TCDs and different L-Glus
FIG. 11 ratio of absorbance signals (A) after the effect of enantiomeric excesses of L-TCDs and different L-Glus461/A618) Variation diagram of
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the drawings of the embodiments of the present invention. It is to be understood that the embodiments described are only a few embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the described embodiments of the invention without any inventive step, are within the scope of protection of the invention.
Chiral carbon point L-TCDs are synthesized according to a one-pot hydrothermal method.
FIG. 1 is a transmission electron micrograph of the synthesized L-TCDs, and FIG. 2 is a circular dichroism spectrum of the synthesized L-TCDs. The above characterization indicates the successful synthesis of carbon point L-TCDs and the chirality of the synthesized carbon point.
Example 1
1. To a 5mL centrifuge tube containing 10. mu. L L-TCDs, 3.0mL of Tris-HCl buffer solution at pH 7.40 was added, followed by 15. mu. L H2O2The solution (1mol/L) is yellow after incubation in a water bath at 70 ℃ for 30 min.
2. To a 5mL centrifuge tube containing 10. mu. L L-TCDs, 2.7mL of Tris-HCl buffer solution with pH 7.40 was added, followed by 15. mu. L H2O2The solution (1mol/L) and the 300 mu L L-Glu (0.1mol/L) solution are yellow after being incubated in a water bath at 70 ℃ for 30 min.
3. To a 5mL centrifuge tube containing 10. mu. L L-TCDs solution, 2 was added7mL of Tris-HCl buffer pH 7.40, followed by 15. mu. L H2O2The solution (1mol/L) and the 300 mu L D-Glu (0.1mol/L) solution are light blue after incubation in a water bath at 70 ℃ for 30 min.
Example 2
1. mu.L of L-TCDs solution was dispersed in 10mM Tris-HCl (pH 7.40) buffer, and then 15. mu.L of H was added2O2Solution (1mol/L) and L-Glu solution with different concentrations are always kept at the total volume of 3 mL. Mixing the above solutions, incubating in 70 deg.C water bath for 30min, and measuring ultraviolet-visible spectrum. As shown in FIGS. 3 and 5, the color of the solution gradually turned yellow with the increase of the concentration of L-Glu, and the absorbance signal ratio (A) thereof461/A618) And gradually increases. As shown in FIG. 8, absorbance signal ratio (A) 461/A618) Can be quantitatively analyzed in a linear manner with the concentration of L-Glu in the range of 0.5mM-12mM according to the concentration of L-Glu and the absorbance signal ratio (A)461/A618) Establishing a standard curve, and establishing a regression equation of 2.7068+0.1611 x [ L-Glu × ]],R20.9946, the detection limit can reach 0.489 mM.
2. mu.L of the L-TCDs solution was dispersed in 10mM Tris-HCl (pH 7.40) buffer, and then 15. mu.L of H was added2O2Solution (1mol/L) and D-Glu solution with different concentrations, wherein the total volume of the mixed solution is always kept at 3 mL. Mixing the above solutions, incubating in 70 deg.C water bath for 30min, and measuring ultraviolet-visible spectrum. As shown in FIGS. 4 and 6, the solution color remained substantially bluish with increasing concentration of D-Glu, and the absorbance signal ratio (A) was substantially unchanged461/A618) No obvious change. FIG. 7 shows the ratio of absorbance signals (A) after L-TCDs have reacted with various concentrations of glutamic acid enantiomer461/A618) With respect to the different enantiomers, a clear signal difference was observed.
Example 3
mu.L of L-TCDs solution was dispersed in 10mM Tris-HCl (pH 7.40) buffer, and then 15. mu.L of H was added2O2Solution (1mol/L) and enantiomeric excess values of different L-type enantiomers (ee ═ CL-CD)/(CL+CD) ) was added to the glutamic acid solution, and the total volume of the mixed solution was always kept at 3 mL. Mixing the above solutions, incubating in 70 deg.C water bath for 30min, and measuring ultraviolet-visible spectrum. As shown in FIGS. 9 and 10, the absorbance signal always remained substantially constant when D-Glu was present in the solution, and only when the enantiomeric excess of the L-form was 100%, that is, all the amino acids contained in the solution were L-Glu, the absorbance intensity became large, the color of the solution also remained bluish in the presence of D-Glu, and the color of the system became yellow when all the enantiomers added were L-Glu. FIG. 11 shows the absorbance ratio (A) 461/A618) And the enantiomeric excess of L-Glu.
Claims (4)
1. The application of chiral carbon dots (L-TCDs) in chiral colorimetric identification of glutamic acid enantiomers.
2. The use according to claim 1, characterized in that the carbon dots with chirality of the synthesis, under the action of hydrogen peroxide, are capable of performing chiral recognition on the glutamic acid enantiomer and exhibit excellent enantioselective colorimetric response and absorbance signal difference.
3. The use according to claim 2, wherein the chiral colorimetric identification method of glutamic acid enantiomers based on chiral carbon points L-TCDs comprises:
(1) synthesis of L-TCDs;
(2) dispersing an appropriate amount of the L-TCDs solution synthesized in the step (1) in Tris-HCl (pH 7.40), and adding an appropriate amount of hydrogen peroxide (H) to the solution2O2) Then adding an L-glutamic acid (L-Glu) or D-glutamic acid (D-Glu) solution, reacting for a period of time at a certain temperature, observing the color change of the solution and scanning an ultraviolet-visible absorption spectrum;
(3) judging the detection result according to the color change and the absorbance intensity of the solution in the step (2), wherein the color of the solution is changed from light blue to yellow, and an absorbance signal A461/A618The L-glutamic acid is obviously increased, on the contrary, the solution color keeps light blue and the absorbance signal A is kept 461/A618D-glutamic acid was used without significant change.
4. The use according to claim 3, wherein the mass ratio of the main raw materials for synthesizing L-TCDs in step (1) is OTD: L-Trp ═ 1: 1.25; step (2) wherein H2O2The concentration of (A) is 5mM, the reaction temperature is 70 ℃, and the reaction time is 30 min; the maximum difference ratio (I) between the signal values of D and L enantiomers in step (3)D/IL)maxAnd was 8.16.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115386372A (en) * | 2022-09-21 | 2022-11-25 | 中国科学院兰州化学物理研究所 | Preparation of chiral fluorescent carbon dots and application of chiral fluorescent carbon dots in identification and detection of tyrosine enantiomers |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115386372A (en) * | 2022-09-21 | 2022-11-25 | 中国科学院兰州化学物理研究所 | Preparation of chiral fluorescent carbon dots and application of chiral fluorescent carbon dots in identification and detection of tyrosine enantiomers |
| CN115386372B (en) * | 2022-09-21 | 2023-05-26 | 中国科学院兰州化学物理研究所 | Preparation of chiral fluorescent carbon dots and application of chiral fluorescent carbon dots in identification and detection of tyrosine enantiomers |
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