Preparation method and application of fluorescent probe for rapidly recognizing glutamine enantiomers

Abstract

The invention relates to a preparation method and application of a fluorescent probe for rapidly recognizing glutamine enantiomers, and belongs to the technical field of fluorescent materials and chiral recognition. The method comprises the following steps: 1, preparing aminated UIO-66; and (2) preparing the L-Cys / UIO-66. The prepared aminated UIO-66 is a three-dimensional rigid MOFs with zirconium as a metal center and 2-amino-1, 4-phthalic acid as an organic ligand, the preparation method of the aminated UIO-66 is mature and simple, the stability is good, the aminated UIO-66 has an excellent luminescence characteristic, and rich active functional groups and unsaturated coordinated Zr6 clusters on the surface can be modified again; according to the invention, L-cysteine is used as a modifier, the chiral modified aminated UIO-66 is prepared from aminated UIO-66 and L-cysteine through a solvothermal method, and the chiral modified aminated UIO-66 is used as a fluorescent probe, so that D / L-Gln can be quickly and effectively recognized, and the D-Gln can be sensitively and quantitatively analyzed.

Description

Technical Field

[0001] The invention belongs to the technical field of fluorescent materials and chiral recognition, and particularly relates to a preparation method and application of a fluorescent probe for rapidly identifying glutamine enantiomers. Background Art

[0002] Chirality is a basic property of nature and one of the most important characteristics of the life process. The vast majority of amino acids that make up life proteins (except glycine) are chiral. Glutamine (Gln), as a non-essential amino acid, is not only the main unit of protein in living organisms, but also the free amino acid with the highest content in the body's blood circulation. Its carbon can be used for the synthesis of amino acids and fatty acids, and its nitrogen can be used for the synthesis of purines and pyrimidines. In addition, Gln reacts with water to produce glutamate and ammonia, which helps neutralize hydrogen ions in the kidneys and maintain acid-base balance. Gln is also essential for muscle synthesis, can prevent muscle atrophy, and is used to treat muscular dystrophy. Recent studies have also found that glutamine is closely related to the growth and proliferation of tumors and cancer cells [Nature.2021,593(7858):282.]. It can be seen that glutamine plays an important role in life activities, and almost all of them are the effects of L-Gln. However, D-Gln will directly reflect the condition of a certain disease. For example, the D-Gln content in the DNA of gastric cancer patients can directly reflect the patient's condition. [Analytical and Bioanalytical Chemistry. 2020, 412(17): 4135.]. Therefore, it is of great practical significance to simply, economically, quickly and effectively identify Gln enantiomers (D / L-Gln) and quantitatively analyze D-Gln.

[0003] At present, the separation and detection technologies of D / L-Gln mainly include chromatographic separation (GC, HPLC) and electromigration (CE, CEC). However, the former has problems such as complex sample pretreatment, expensive instruments and chiral chromatographic columns, long time consumption and low sensitivity [Animal Biotechnology.2022,33(6):1109.Aids.2024,38(3):299-308.]; the latter has shortcomings such as small injection volume, cumbersome column preparation process, poor reproducibility and stability [Journal ofSeparation Science.2024,47(3).][Journal of Chromatography A.2018,1548:104.]. In comparison, fluorescence detection has the advantages of high sensitivity, fast speed, easy operation and low cost, and fluorescent sensing materials are the core of this analytical method. The fluorescent materials currently used for chiral recognition include: chiral luminophores [Coordination Chemistry Reviews. 2020, 527: 213329.], nanomaterials [Angewandte Chemie-International Edition. 2023, 62 (28).], fluorescent covalent organic frameworks (LCOFs) [Spectrochimica Acta Part a-Molecular and Biomolecular Spectroscopy. 2023, 605: 122370.] and fluorescent metal organic frameworks (LMOFs) [Electrochimica Acta. 2022, 506: 139809.], etc. Although these fluorescent materials have certain advantages, they still have some shortcomings when targeting specific analytes, such as: the preparation method of chiral luminophores is relatively complicated, the biocompatibility of LCOFs is not friendly enough, and the water dispersibility of nanomaterials is poor, which limits their practical applications. Summary of the invention

[0004] In order to solve the above technical problems, the present invention provides a preparation method and application of a fluorescent probe for rapidly identifying glutamine enantiomers.

[0005] The present invention provides a fluorescence detection method that can quickly and effectively identify D / L-Gln and sensitively detect D-Gln. The aminated UIO-66 prepared by the present invention is a three-dimensional rigid MOFs composed of zirconium as a metal center and 2-amino-1,4-phthalic acid as an organic ligand. It not only has a mature and simple preparation method, good stability, and excellent luminescence characteristics, but also has abundant active functional groups (-NH2, -COOH) and unsaturated coordinated Zr6 clusters on the surface that can be further modified; the present invention applies the chirally modified aminated UIO-66 in the field of chiral recognition fluorescence sensing; the present invention uses L-cysteine ​​(L-Cys) as a modifier, and prepares a chirally modified aminated UIO-66 (L-Cys / UIO-66) by a solvothermal method, and uses it as a fluorescent probe, which can quickly and effectively identify D / L-Gln and sensitively and quantitatively analyze D-Gln.

[0006] A method for preparing a fluorescent probe for rapid identification of glutamine enantiomers is specifically completed by the following steps:

[0007] 1. Preparation of amino UIO-66:

[0008] Dissolving zirconium tetrachloride and 2-amino-1,4-phthalic acid in N,N-dimethylformamide to obtain a mixed solution; transferring the mixed solution to a Teflon-lined reactor, and then placing the reactor at a temperature of 120° C. to 130° C. for hydrothermal reaction to obtain a reaction product; centrifuging the reaction product, collecting solid matter, and then washing and vacuum drying the collected solid matter to obtain amino UIO-66;

[0009] 2. Preparation of L-Cys / UIO-66:

[0010] The aminated UIO-66 and L-cysteine ​​are added to N,N-dimethylformamide, ultrasonically dissolved, sealed, and reacted at 120°C to 130°C for a period of time. After the reaction is completed, it is cooled to room temperature and centrifuged to collect the solid matter produced in the reaction system. The solid matter is washed and vacuum dried to obtain L-Cys / UIO-66, which is a fluorescent probe for rapid identification of glutamine enantiomers.

[0011] A fluorescent probe for rapid identification of glutamine enantiomers is used in the fluorescence identification of glutamine enantiomers.

[0012] Beneficial effects of the present invention:

[0013] 1. The fluorescent probe (L-Cys / UIO-66) for rapid identification of glutamine enantiomers prepared by the present invention has a simple preparation method, low cost, good crystallinity and regular crystal morphology;

[0014] 2. The fluorescent probe (L-Cys / UIO-66) for rapid identification of glutamine enantiomers prepared by the present invention can quickly (1.0 min) effectively (Q R =0.87) chiral recognition, and a wide pH range of application (pH = 6.0-10.0);

[0015] 3. The fluorescent probe (L-Cys / UIO-66) for rapid identification of glutamine enantiomers prepared by the present invention can be used as a fluorescent probe to detect D-Gln (20-500 μmol L -1 ) for sensitive quantitative analysis (LOD = 4.82 μmol L -1 ). BRIEF DESCRIPTION OF THE DRAWINGS

[0016] Figure 1 The scanning electron microscope images and energy spectrum images of the amino UIO-66 and L-Cys / UIO-66 prepared in Example 1;

[0017] Figure 2 FT-IR images of amino UIO-66 and L-Cys / UIO-66 prepared in Example 1;

[0018] Figure 3 XRD pattern of L-Cys / UIO-66 prepared in Example 1;

[0019] Figure 4 This is a fluorescence recognition diagram of nine amino acid enantiomers using L-Cys / UIO-66 prepared in Example 1;

[0020] Figure 5 The fluorescence spectrum of the optimal contact time of D-Gln detected by using L-Cys / UIO-66 prepared in Example 1 in Example 2;

[0021] Figure 6 The fluorescence spectrum of the applicable range of pH value of D-Gln detected by using L-Cys / UIO-66 prepared in Example 1 in Example 3;

[0022] Figure 7 The fluorescence spectrum and standard curve diagram of the quantitative detection of D-Gln using L-Cys / UIO-66 prepared in Example 1 in Example 4 are shown. DETAILED DESCRIPTION

[0023] Specific implementation method 1: This implementation method is a method for preparing a fluorescent probe for rapid identification of glutamine enantiomers, which is specifically completed according to the following steps:

[0024] 1. Preparation of amino UIO-66:

[0025] Dissolving zirconium tetrachloride and 2-amino-1,4-phthalic acid in N,N-dimethylformamide to obtain a mixed solution; transferring the mixed solution to a Teflon-lined reactor, and then placing the reactor at a temperature of 120° C. to 130° C. for hydrothermal reaction to obtain a reaction product; centrifuging the reaction product, collecting solid matter, and then washing and vacuum drying the collected solid matter to obtain amino UIO-66;

[0026] 2. Preparation of L-Cys / UIO-66:

[0027] The aminated UIO-66 and L-cysteine ​​are added to N,N-dimethylformamide, ultrasonically dissolved, sealed, and reacted at 120°C to 130°C for a period of time. After the reaction is completed, it is cooled to room temperature and centrifuged to collect the solid matter produced in the reaction system. The solid matter is washed and vacuum dried to obtain L-Cys / UIO-66, which is a fluorescent probe for rapid identification of glutamine enantiomers.

[0028] Specific embodiment 2: This embodiment differs from specific embodiment 1 in that: the mass ratio of zirconium tetrachloride to 2-amino-1,4-phthalic acid in step 1 is (40-50):(30-40); the mass ratio of zirconium tetrachloride to N,N-dimethylformamide in step 1 is (40mg-50mg):(20mL-30mL). The other steps are the same as those in specific embodiment 1.

[0029] Specific implementation method 3: This implementation method is different from specific implementation method 1 or 2 in that the time of the hydrothermal reaction in step 1 is 10 h to 12 h. The other steps are the same as those in specific implementation method 1 or 2.

[0030] Specific embodiment 4: This embodiment differs from specific embodiments 1 to 3 in that the centrifugal speed in step 1 is 6000 rpm to 8000 rpm and the centrifugal time is 5 min to 8 min. The other steps are the same as those in specific embodiments 1 to 3.

[0031] Specific embodiment 5: This embodiment differs from specific embodiments 1 to 4 in that: in step 1, N,N-dimethylformamide and methanol are used to wash the collected solid matter 3 to 5 times respectively; the vacuum drying temperature in step 1 is 60°C to 80°C, and the vacuum drying time is 10h to 12h. The other steps are the same as those of specific embodiments 1 to 4.

[0032] Specific embodiment 6: This embodiment differs from specific embodiments 1 to 5 in that the molar ratio of the amino UIO-66 to L-cysteine ​​in step 2 is 1:(7-9); the volume ratio of the amino UIO-66 to N,N-dimethylformamide in step 2 is (30 mg-50 mg):3 mL. The other steps are the same as those in specific embodiments 1 to 5.

[0033] Specific embodiment 7: This embodiment differs from specific embodiments 1 to 6 in that the reaction time at 120° C. to 130° C. in step 2 is 22 h to 26 h. The other steps are the same as those of specific embodiments 1 to 6.

[0034] Specific embodiment 8: This embodiment differs from specific embodiments 1 to 7 in that the centrifugal speed in step 2 is 6000 rpm to 8000 rpm and the centrifugal time is 5 min to 8 min. The other steps are the same as those of specific embodiments 1 to 7.

[0035] Specific embodiment 9: This embodiment differs from specific embodiments 1 to 8 in that: in step 2, N,N-dimethylformamide and methanol are used to wash the solid material 3 to 5 times respectively; the vacuum drying temperature in step 2 is 60°C to 80°C, and the vacuum drying time is 10h to 12h. The other steps are the same as those of specific embodiments 1 to 8.

[0036] Specific embodiment 10: This embodiment is an application of a fluorescent probe for rapid identification of glutamine enantiomers in fluorescent identification of glutamine enantiomers.

[0037] The following examples are used to verify the beneficial effects of the present invention:

[0038] Example 1: A method for preparing a fluorescent probe for rapid identification of glutamine enantiomers is specifically completed by the following steps:

[0039] 1. Preparation of amino UIO-66:

[0040] 46.7 mg of zirconium tetrachloride and 36.3 mg of 2-amino-1,4-benzenedicarboxylic acid were dissolved in 20.4 mL of N,N-dimethylformamide to obtain a mixed solution; the mixed solution was transferred to a 50 mL Teflon-lined reactor, and the reactor was placed in a temperature of 120° C. for hydrothermal reaction for 12 hours to obtain a reaction product; the reaction product was centrifuged at a speed of 8000 rpm for 5 minutes, and the solid matter was collected, and the collected solid matter was washed three times with N,N-dimethylformamide and methanol respectively, and finally vacuum dried at 80° C. for 12 hours to obtain amino UIO-66;

[0041] 2. Preparation of L-Cys / UIO-66:

[0042] 39.3 mg of amino UIO-66 and L-cysteine ​​were added to 3.0 mL of N, N-dimethylformamide, ultrasonically dissolved, sealed, and reacted at 120°C for 24 h. After the reaction was completed, the mixture was cooled to room temperature and centrifuged at 8000 rpm for 5 min. The solid matter produced in the reaction system was collected, and the solid matter was washed three times with N, N-dimethylformamide and methanol respectively, and finally vacuum dried at 80°C for 12 h to obtain L-Cys / UIO-66, which is a fluorescent probe for rapid identification of glutamine enantiomers (L-Cys / UIO-66);

[0043] The molar ratio of the amino UIO-66 to L-cysteine ​​described in step 2 is 1:8.

[0044] The crystal morphology and element distribution of amino UIO-66 and L-Cys / UIO-66 were investigated by scanning electron microscopy and energy dispersive spectrometer. Figure 1 As shown;

[0045] Figure 1 The scanning electron microscope images and energy spectrum images of the amino UIO-66 and L-Cys / UIO-66 prepared in Example 1;

[0046] from Figure 1 It can be seen that the amino UIO-66 synthesized in Example 1 has a clear octahedral morphology and uniform element distribution. The modified L-Cys / UIO-66 after synthesis becomes rough due to the surface loading of L-cysteine ​​(L-Cys), but the original octahedral crystal morphology of the UIO-66 material is maintained as a whole, with a long diameter of about 200nm and a short diameter of about 150nm. The surface elements are evenly distributed and the characteristic S element in L-Cys is introduced, indicating that L-Cys / UIO-66 is successfully prepared.

[0047] Figure 2 FT-IR images of amino UIO-66 and L-Cys / UIO-66 prepared in Example 1;

[0048] from Figure 2 It was observed that L-Cys / UIO-66 contained most of the characteristic peaks of amino UIO-66, such as 3340 and 3470 cm -1 Symmetric and asymmetric stretching vibrations of NH and OH, 1580-1440cm -1 The peak at 670 cm is the benzene ring skeleton stretching vibration absorption peak. -1 is the stretching vibration absorption peak of Zr-O. In addition, compared with amino UIO-66, L-Cys / UIO-66 is located at 1510 cm-1 The absorption peak at 2570cm-1 is enhanced due to the conjugation between the carboxyl carbonyl group and the benzene ring, forming a conjugated delocalized π bond, which causes the absorption peak to move to a low frequency. -1 The weak absorption peak at 1630 cm-1 proves the existence of -SH in L-Cys [Acs Applied Materials & Interfaces. 2019, 11(50): 46973-46983.] -1 and 1120cm -1 The two new characteristic peaks appearing at are related to the stretching vibration of the carboxyl carbonyl in L-Cys and the CN in the aliphatic group. The above results show that the chiral modifier (L-Cys) occupies the remaining Zr6 cluster vacancies on the amino UIO-66 through the solvent-assisted ligand method (SALE), and this example successfully prepares L-Cys / UIO-66.

[0049] The L-Cys / UIO-66 material was characterized by X-ray diffractometer. Figure 3 As shown;

[0050] Figure 3 XRD pattern of L-Cys / UIO-66 prepared in Example 1;

[0051] The XRD diffraction pattern of L-Cys / UIO-66 is basically consistent with the standard diffraction spectrum of amino UIO-66 reported in the literature [Acs Sustainable Chemistry & Engineering. 2019, 7 (3): 3203-3212.], and the diffraction peak is sharp, indicating that the prepared L-Cys / UIO-66 has a high degree of crystallinity and well retains the original crystal structure of amino UIO-66.

[0052] The above contents indicate that this example successfully prepared LMOF, L-Cys / UIO-66, with good crystallinity, regular crystal morphology, and uniform element distribution.

[0053] Application Example 1: Fluorescence recognition of nine amino acid enantiomers using L-Cys / UIO-66 prepared in Example 1 was performed according to the following steps:

[0054] Accurately weigh 2 mg of L-Cys / UIO-66 powder prepared in Example 1 and disperse it in 400 mL of ultrapure water to prepare a concentration of 5.0 μg mL -1 The probe suspension was obtained by adding L-Cys / UIO-66 solution, measuring its fluorescence emission spectrum and recording the emission peak intensity at the optimal excitation wavelength (330 nm) as F0. -1Aqueous solutions of amino acids (histidine, proline, phenylalanine, α-alanine, isoleucine, tryptophan, threonine, serine, glutamine) with different configurations (L- and D-). 3.0 mL of the prepared probe solution was mixed with 20 μL of aqueous solutions of amino acids with different configurations, and allowed to stand for 1.0 min. The fluorescence emission spectra of the mixed solutions were measured at the optimal excitation wavelength and recorded as F1 and F2. The fluorescence intensity ratios (F1 / F0 or F2 / F0) of the same amino acid with different configurations were calculated and compared to determine the selectivity of the chiral fluorescent probe. The quenching ratio (Q R = F2 / F1) as the evaluation index of chiral recognition selectivity, and evaluate the chiral selectivity of L-Cys / UIO-66 for amino acid enantiomers. Figure 4 As shown in the figure, it can be observed that L-Cys / UIO-66 exhibits weak fluorescence response (F1 / F0 or F2 / F0≈1.0) to eight amino acid enantiomers (histidine, proline, phenylalanine, α-alanine, isoleucine, tryptophan, threonine, and serine), while it has the best chiral recognition effect on D / L-Gln (Q R =0.87) is lower than the other eight amino acids (Q R ≈1.0).

[0055] The above content indicates that the L-Cys / UIO-66 prepared in Example 1 can specifically distinguish D- and L-Gln, and can perform quantitative analysis on D-Gln.

[0056] Application Example 2: The fluorescence spectrum of the optimal contact time of D-Gln was detected by using L-Cys / UIO-66 prepared in Example 1, and the following steps were performed:

[0057] Accurately weigh 2 mg of L-Cys / UIO-66 powder prepared in Example 1 and disperse it in 400 mL of ultrapure water to prepare a concentration of 5.0 μg mL -1 3.0 mL of the probe solution was mixed with 20 μL of D-Gln solution (75.0 mmol L -1 ) and mixed. At different contact times (0.50min, 1.0min, 1.5min, 2.0min, 2.5min, 3.0min), the fluorescence emission spectrum of the mixed solution was measured according to the fluorescence measurement method in Application Example 1, and the maximum emission peak intensity F was recorded. The fluorescence intensity ratio F / F0 was used as an evaluation index to determine the optimal contact time. The results are shown in FIG. Figure 5 As shown in the figure, with the increase of contact time, the F / F0 of D-Gln and L-Cys / UIO-66 showed a trend of first decreasing and then gradually stabilizing, and the fluorescence intensity did not change significantly after 1.0 min.

[0058] The above contents indicate that the L-Cys / UIO-66 prepared in Example 1 can realize the rapid detection of D-Gln.

[0059] Application Example 3: The fluorescence spectrum of the applicable pH range of D-Gln was detected using L-Cys / UIO-66 prepared in Example 1, and the following steps were performed:

[0060] Using 1.0 mol L -1 NaOH solution and 1.0 mol L -1 L-Cys / UIO-66 solutions (5.0 μg mL -1 ). The probe solutions with different pH values ​​were mixed with D-Gln (75 mmol L -1 ) and allowed to stand for 1.0 min. The fluorescence spectrum was measured according to the fluorescence measurement method in Application Example 1, and the maximum emission peak intensity F was recorded. The applicable pH range of the chiral fluorescent probe for detecting D-Gln was determined based on F / F0. Figure 6 As shown, the fluorescence intensity ratio F / F0 of D-Gln and L-Cys / UIO-66 remained basically unchanged at pH = 6.0-10.0, indicating that L-Cys / UIO-66 can stably recognize D-Gln in the range of pH = 6.0-10.0.

[0061] The above contents show that the L-Cys / UIO-66 prepared in Example 1 has a wide pH applicable range for D-Gln detection, which is beneficial for practical application.

[0062] Application Example 4: Quantitative detection and analysis of D-Gln using L-Cys / UIO-66 prepared in Example 1 was performed according to the following steps:

[0063] Accurately weigh 2 mg of L-Cys / UIO-66 powder prepared in Example 1 and disperse it in 400 mL of ultrapure water to prepare a concentration of 5.0 μg mL -1 3.0 mL of the probe solution was mixed with 20 μL of 3.0-75.0 mmol L -1 The D-Gln solution was mixed and allowed to stand for 1.0 min. The fluorescence spectrum was measured according to the fluorescence measurement method in Application Example 1, and the maximum emission peak intensity F was recorded. A standard curve was constructed with the D-Gln concentration as the abscissa and the fluorescence intensity ratio F / F0 as the ordinate. The results are shown in Figure 7. As the D-Gln concentration increases, the fluorescence intensity of the mixed solution at the maximum emission peak gradually weakens. The fluorescence intensity ratio F / F0 is proportional to the D-Gln concentration in the range of 20 to 500 μmol L -1A good linear relationship is shown in the concentration range, and the linear equation is F / F0=0.001081[Gln]+0.01929, R 2 =0.99807, detection limit is 4.82 μmol L -1 .

[0064] The above results show that L-Cys / UIO-66 prepared in Example 1 can sensitively detect D-Gln.

Claims

1. A method for preparing a fluorescent probe for rapid identification of glutamine enantiomers, characterized in that The preparation method is specifically completed according to the following steps:

1. Preparation of amino UIO-66: Dissolving zirconium tetrachloride and 2-amino-1,4-phthalic acid in N,N-dimethylformamide to obtain a mixed solution; transferring the mixed solution to a Teflon-lined reactor, and then placing the reactor at a temperature of 120° C. to 130° C. for hydrothermal reaction to obtain a reaction product; centrifuging the reaction product, collecting solid matter, and then washing and vacuum drying the collected solid matter to obtain amino UIO-66; 2. Preparation of L-Cys / UIO-66: The aminated UIO-66 and L-cysteine ​​are added to N,N-dimethylformamide, ultrasonically dissolved, sealed, and reacted at 120°C to 130°C for a period of time. After the reaction is completed, it is cooled to room temperature and centrifuged to collect the solid matter produced in the reaction system. The solid matter is washed and vacuum dried to obtain L-Cys / UIO-66, which is a fluorescent probe for rapid identification of glutamine enantiomers.

2. The method for preparing a fluorescent probe for rapid identification of glutamine enantiomers according to claim 1, characterized in that The mass ratio of zirconium tetrachloride and 2-amino-1,4-phthalic acid described in step 1 is (40-50):(30-40); the volume ratio of zirconium tetrachloride and N,N-dimethylformamide described in step 1 is (40mg-50mg):(20mL-30mL).

3. The method for preparing a fluorescent probe for rapid identification of glutamine enantiomers according to claim 1, characterized in that The time of the hydrothermal reaction in step 1 is 10 h to 12 h.

4. The method for preparing a fluorescent probe for rapid identification of glutamine enantiomers according to claim 1, characterized in that The centrifugal speed in step 1 is 6000 rpm to 8000 rpm, and the centrifugal time is 5 min to 8 min.

5. The method for preparing a fluorescent probe for rapid identification of glutamine enantiomers according to claim 1, characterized in that In step 1, the collected solid matter is washed 3 to 5 times with N,N-dimethylformamide and methanol respectively; the vacuum drying temperature in step 1 is 60° C. to 80° C., and the vacuum drying time is 10 h to 12 h.

6. The method for preparing a fluorescent probe for rapid identification of glutamine enantiomers according to claim 1, characterized in that The molar ratio of the amino UIO-66 and L-cysteine ​​described in step 2 is 1:(7-9); the volume ratio of the amino UIO-66 described in step 2 to N,N-dimethylformamide is (30mg-50mg):3mL.

7. The method for preparing a fluorescent probe for rapid identification of glutamine enantiomers according to claim 1, characterized in that The reaction time in step 2 at 120° C. to 130° C. is 22 h to 26 h.

8. The method for preparing a fluorescent probe for rapid identification of glutamine enantiomers according to claim 1, characterized in that The centrifugal speed in step 2 is 6000 rpm to 8000 rpm, and the centrifugal time is 5 min to 8 min.

9. The method for preparing a fluorescent probe for rapid identification of glutamine enantiomers according to claim 1, characterized in that In step 2, the solid matter is washed 3 to 5 times with N,N-dimethylformamide and methanol respectively; the vacuum drying temperature in step 2 is 60° C. to 80° C., and the vacuum drying time is 10 h to 12 h.

10. Use of a fluorescent probe for rapid identification of glutamine enantiomers prepared by the preparation method according to claim 1, characterized in that A fluorescent probe for rapid identification of glutamine enantiomers is used in the fluorescence identification of glutamine enantiomers.

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