Preparation method and application of a fluorescence probe for rapid identification of glutamine enantiomers
By preparing a chiral-modified aminoated UIO-66 fluorescent probe, the problem of complex and time-consuming D/L-Gln detection in the prior art has been solved, realizing rapid and sensitive D/L-Gln identification and quantitative analysis, which is suitable for the field of chiral identification.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- QIQIHAR UNIVERSITY
- Filing Date
- 2024-09-11
- Publication Date
- 2026-07-14
AI Technical Summary
Existing D/L-Gln separation and detection technologies suffer from problems such as complex sample processing, expensive instruments, long processing time, and low sensitivity. Fluorescent materials also have shortcomings in chiral recognition, including complex preparation, poor biocompatibility, and poor dispersibility in water systems.
A chiral modified amino-modified UIO-66 (L-Cys/UIO-66) fluorescent probe was prepared by using zirconium as the metal center and 2-amino-1,4-phthalic acid as the organic ligand, and by modifying it with L-cysteine via a solvothermal method, for the rapid identification of D/L-Gln.
It achieves rapid and effective chiral identification and sensitive quantitative analysis. The preparation method is simple and low-cost, with good crystallinity and a wide pH range. It can identify D/L-Gln and perform quantitative analysis of D-Gln within 1 minute, with high sensitivity and a detection limit of 4.82 μmol L-1.
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Figure CN119120009B_ABST
Abstract
Description
Technical Field
[0001] This invention belongs to the field of fluorescent materials and chiral recognition technology, specifically relating to a method for preparing and applying a rapid fluorescent probe for recognizing glutamine enantiomers. Background Technology
[0002] Chirality is a fundamental property of nature and one of the most important characteristics of life processes. The vast majority of amino acids that make up proteins (except glycine) are chiral. Glutamine (Gln), as a non-essential amino acid, is not only a major building block of proteins in living organisms but also the most abundant free amino acid in the bloodstream. Its carbon can be used in the synthesis of amino acids and fatty acids, and its nitrogen can be used in the synthesis of purines and pyrimidines. Furthermore, Gln reacts with water to produce glutamate and ammonia, which help neutralize hydrogen ions in the kidneys and maintain acid-base balance. Gln is also crucial for muscle synthesis, preventing muscle atrophy and is used to treat muscular dystrophy. Recent studies have also found a close relationship between glutamine and the growth and proliferation of tumors and cancer cells [Nature. 2021, 593(7858):282.]. It is evident that glutamine plays an important role in life activities, and almost all of this is due to the action of L-Gln. However, D-Gln can directly reflect certain disease conditions; for example, the D-Gln content in the DNA of gastric cancer patients can directly reflect the patient's disease status. [Analytical and Bioanalytical Chemistry. 2020, 412(17): 4135.]. Therefore, the simple, economical, rapid and effective identification of Gln enantiomers (D / L-Gln) and the quantitative analysis of D-Gln are of great practical significance.
[0003] Currently, the main separation and detection techniques for D / L-Gln are 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 processing time 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 of Separation Science.2024,47(3).][Journal of Chromatography A.2018,1548:104.]. In comparison, fluorescence detection has advantages such as high sensitivity, fast speed, ease of operation, and low cost. Fluorescent sensing materials are the core of this analytical method. Currently, fluorescent materials used for chiral recognition include: chiral luminescent groups [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. While these fluorescent materials all have certain advantages, they still have some shortcomings when targeting specific analytes. For example, the preparation methods of chiral luminescent groups are relatively complex, LCOFs are not biocompatible, and nanomaterials have poor water dispersibility, which limits their practical applications. Summary of the Invention
[0004] To address the aforementioned technical problems, this invention provides a method for preparing and applying a rapid fluorescent probe for identifying glutamine enantiomers.
[0005] This invention provides a rapid and effective fluorescence detection method for identifying D / L-Gln and sensitively detecting D-Gln. The aminated UIO-66 prepared in this invention is a three-dimensional rigid MOF composed of zirconium as the metal center and 2-amino-1,4-phthalic acid as the organic ligand. It not only has a mature, simple, and stable preparation method and excellent luminescent properties, but also possesses abundant surface active functional groups (-NH2, -COOH) and unsaturated coordinated Zr6 clusters that can be further modified. This invention applies the chiral-modified aminated UIO-66 to the field of chiral recognition fluorescence sensing. Using L-cysteine (L-Cys) as a modifier, this invention prepares a chiral-modified aminated UIO-66 (L-Cys / UIO-66) via a solvothermal method. Using this as a fluorescent probe, it can rapidly and effectively identify D / L-Gln and perform sensitive quantitative analysis of D-Gln.
[0006] A method for preparing a rapid fluorescent probe for identifying glutamine enantiomers, specifically comprising the following steps:
[0007] I. Preparation of amination-modified UIO-66:
[0008] Zirconium tetrachloride and 2-amino-1,4-phthalic acid were dissolved in N,N-dimethylformamide to obtain a mixed solution. The mixed solution was transferred to a Teflon-lined reactor, and the reactor was placed in a hydrothermal reaction at a temperature of 120℃~130℃ to obtain the reaction product. The reaction product was centrifuged, the solid material was collected, and the collected solid material was washed and vacuum dried to obtain aminated UIO-66.
[0009] II. Preparation of L-Cys / UIO-66:
[0010] Aminated UIO-66 and L-cysteine were added to N,N-dimethylformamide, dissolved by sonication, sealed, and then reacted at 120℃~130℃ for a period of time. After the reaction was completed, the mixture was cooled to room temperature, centrifuged, and the solid material produced in the reaction system was collected. The solid material was washed and vacuum dried to obtain L-Cys / UIO-66, which is the rapid recognition enantiomer fluorescent probe for glutamine.
[0011] Application of a rapid fluorescent probe for identifying glutamine enantiomers in glutamine enantiomer fluorescence recognition.
[0012] The beneficial effects of this invention are:
[0013] I. The rapid glutamine enantiomer fluorescent probe (L-Cys / UIO-66) prepared by this invention has a simple preparation method, low cost, good crystallinity, and regular crystal morphology.
[0014] II. The rapid recognition probe (L-Cys / UIO-66) for glutamine enantiomeric fluorescence prepared in this invention can rapidly (1.0 min) and effectively (Q) identify D / L-Gln. R Chiral recognition with a strength of 0.87, and a wide applicable pH range (pH = 6.0-10.0);
[0015] III. The rapid recognition fluorescent probe for glutamine enantiomers (L-Cys / UIO-66) prepared in this invention can be used as a fluorescent probe for D-Gln (20-500 μmol L). -1 Sensitive quantitative analysis was performed (LOD = 4.82 μmol L). -1 ). Attached Figure Description
[0016] Figure 1 Scanning electron microscope (SEM) images and energy dispersive spectroscopy (EDS) spectra of aminoated UIO-66 and L-Cys / UIO-66 prepared in Example 1;
[0017] Figure 2 FT-IR images of aminated 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 The image shows the fluorescence recognition of nine amino acid enantiomers by L-Cys / UIO-66 prepared in Example 1 in Application Example 1.
[0020] Figure 5 The fluorescence spectrum of the L-Cys / UIO-66 prepared in Example 1 used in Application Example 2 to detect the optimal contact time of D-Gln;
[0021] Figure 6 The fluorescence spectrum of the L-Cys / UIO-66 prepared in Example 1 used in Application Example 3 to detect the pH range of D-Gln;
[0022] Figure 7 The fluorescence spectrum and standard curve of D-Gln quantitative detection using L-Cys / UIO-66 prepared in Example 1 are shown in Application Example 4. Detailed Implementation
[0023] Specific Implementation Method 1: This implementation method provides a rapid method for preparing a fluorescent probe for identifying glutamine enantiomers, which is specifically completed according to the following steps:
[0024] I. Preparation of amination-modified UIO-66:
[0025] Zirconium tetrachloride and 2-amino-1,4-phthalic acid were dissolved in N,N-dimethylformamide to obtain a mixed solution. The mixed solution was transferred to a Teflon-lined reactor, and the reactor was placed in a hydrothermal reaction at a temperature of 120℃~130℃ to obtain the reaction product. The reaction product was centrifuged, the solid material was collected, and the collected solid material was washed and vacuum dried to obtain aminated UIO-66.
[0026] II. Preparation of L-Cys / UIO-66:
[0027] Aminated UIO-66 and L-cysteine were added to N,N-dimethylformamide, dissolved by sonication, sealed, and then reacted at 120℃~130℃ for a period of time. After the reaction was completed, the mixture was cooled to room temperature, centrifuged, and the solid material produced in the reaction system was collected. The solid material was washed and vacuum dried to obtain L-Cys / UIO-66, which is the rapid recognition enantiomer fluorescent probe for glutamine.
[0028] Specific Implementation Method Two: This implementation method differs from Specific Implementation Method One in that the mass ratio of zirconium tetrachloride to 2-amino-1,4-phthalic acid in step one is (40-50):(30-40); the mass ratio of zirconium tetrachloride to N,N-dimethylformamide in step one is (40 mg-50 mg):(20 mL-30 mL). All other steps are the same as in Specific Implementation Method One.
[0029] Specific Implementation Method Three: This implementation method differs from Specific Implementation Method One or Two in that the hydrothermal reaction time in step one is 10-12 hours. The other steps are the same as in Specific Implementation Method One or Two.
[0030] Specific Implementation Method Four: This implementation method differs from Specific Implementation Methods One to Three in that the centrifugation speed in step one is 6000 rpm to 8000 rpm, and the centrifugation time is 5 min to 8 min. The other steps are the same as in Specific Implementation Methods One to Three.
[0031] Specific Implementation Method Five: This implementation method differs from Specific Implementation Methods One to Four in that: in step one, the collected solid material is washed 3 to 5 times with N,N-dimethylformamide and methanol respectively; the vacuum drying temperature in step one is 60℃ to 80℃, and the vacuum drying time is 10h to 12h. Other steps are the same as in Specific Implementation Methods One to Four.
[0032] Specific Implementation Method Six: This implementation method differs from Specific Implementation Methods One to Five in that: the molar ratio of aminoated UIO-66 to L-cysteine in step two is 1:(7-9); the mass ratio of aminoated UIO-66 to the volume ratio of N,N-dimethylformamide in step two is (30mg-50mg):3mL. Other steps are the same as in Specific Implementation Methods One to Five.
[0033] Specific Implementation Method Seven: The difference between this implementation method and Specific Implementation Methods One to Six is that the reaction time at 120℃~130℃ in step two is 22h~26h. The other steps are the same as in Specific Implementation Methods One to Six.
[0034] Specific Implementation Method Eight: This implementation method differs from Specific Implementation Methods One to Seven in that the centrifugation speed in step two is 6000 rpm to 8000 rpm, and the centrifugation time is 5 min to 8 min. The other steps are the same as in Specific Implementation Methods One to Seven.
[0035] Specific Implementation Method Nine: This implementation method differs from Specific Implementation Methods One to Eight in that: in step two, the solid material is washed 3 to 5 times sequentially with N,N-dimethylformamide and methanol; the vacuum drying temperature in step two is 60℃ to 80℃, and the vacuum drying time is 10 to 12 hours. Other steps are the same as in Specific Implementation Methods One to Eight.
[0036] Specific Implementation Method 10: This implementation method is an application of a rapid identification probe for glutamine enantiomers in glutamine enantiomer fluorescence recognition.
[0037] The beneficial effects of the present invention are verified using the following embodiments:
[0038] Example 1: A method for preparing a rapid enantiomeric fluorescent probe for identifying glutamine, specifically comprising the following steps:
[0039] I. Preparation of amination-modified UIO-66:
[0040] 46.7 mg of zirconium tetrachloride and 36.3 mg of 2-amino-1,4-phthalic 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 hydrothermal reaction at 120 °C for 12 h to obtain the reaction product. The reaction product was centrifuged at 8000 rpm for 5 min, and the solid material was collected. The collected solid material was washed three times with N,N-dimethylformamide and methanol respectively. Finally, it was vacuum dried at 80 °C for 12 h to obtain ammoniated UIO-66.
[0041] II. Preparation of L-Cys / UIO-66:
[0042] 39.3 mg of amino-modified UIO-66 and L-cysteine were added to 3.0 mL of N,N-dimethylformamide, dissolved by sonication, 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 material generated in the reaction system was collected and washed three times with N,N-dimethylformamide and methanol respectively. Finally, the solid material was vacuum dried at 80 °C for 12 h to obtain L-Cys / UIO-66, which is the rapid recognition enantiomeric fluorescent probe for glutamine (L-Cys / UIO-66).
[0043] The molar ratio of amino-treated UIO-66 to L-cysteine in step two is 1:8.
[0044] The crystal morphology and elemental distribution of amino-modified UIO-66 and L-Cys / UIO-66 were determined using scanning electron microscopy and energy dispersive spectroscopy, such as... Figure 1 As shown;
[0045] Figure 1 Scanning electron microscope (SEM) images and energy dispersive spectroscopy (EDS) spectra of aminoated UIO-66 and L-Cys / UIO-66 prepared in Example 1;
[0046] from Figure 1 It can be seen that the aminated UIO-66 synthesized in Example 1 has a clear octahedral morphology and uniform elemental distribution. The modified L-Cys / UIO-66 after synthesis becomes rougher due to the surface loading of L-cysteine (L-Cys), but it retains the original octahedral crystal morphology of UIO-66 material as a whole, with a major axis of about 200 nm and a minor axis of about 150 nm. The surface elemental distribution is uniform and the characteristic S element of L-Cys is introduced, indicating that L-Cys / UIO-66 was successfully prepared.
[0047] Figure 2 FT-IR images of aminated UIO-66 and L-Cys / UIO-66 prepared in Example 1;
[0048] from Figure 2 L-Cys / UIO-66 was observed to contain most of the characteristic peaks of aminated UIO-66, such as 3340 and 3470 cm⁻¹. -1 Symmetric and asymmetric stretching vibrations of NH and OH, 1580-1440 cm⁻¹ -1 The absorption peak at 670 cm⁻¹ is the stretching vibration of the benzene ring skeleton. -1 This is the absorption peak for the stretching vibration of Zr-O. Furthermore, compared to amino-treated UIO-66, L-Cys / UIO-66 is located at 1510 cm⁻¹.-1 The absorption peak at 2570 cm⁻¹ shifts to a lower frequency region due to the enhanced conjugation between the carboxyl carbonyl group and the benzene ring, forming conjugated delocalized π bonds. -1 The weak absorption peak at 1630 cm⁻¹ confirms the presence of -SH in L-Cys [Acs Applied Materials & Interfaces. 2019, 11(50): 46973-46983.], 1630 cm⁻¹ -1 and 1120cm -1 The two new characteristic peaks observed are related to the stretching vibrations of the carboxyl carbonyl group in L-Cys and CN in the aliphatic group. These results indicate that the chiral modifier (L-Cys) occupies the remaining Zr6 cluster vacancy on amino UIO-66 via the solvent-assisted ligand method (SALE), and L-Cys / UIO-66 was successfully prepared in this embodiment.
[0049] The L-Cys / UIO-66 material was characterized using X-ray diffraction, such as... 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 pattern of aminated UIO-66 reported in the literature [Acs Sustainable Chemistry & Engineering. 2019, 7(3): 3203-3212.], and the diffraction peak positions are sharp, indicating that the prepared L-Cys / UIO-66 has high crystallinity and retains the original crystal structure of aminated UIO-66 very well.
[0052] The above content shows that this embodiment successfully prepared an LMOF, L-Cys / UIO-66, with good crystallinity, regular crystal morphology, and uniform elemental distribution.
[0053] Application Example 1: The fluorescence recognition of nine amino acid enantiomers was performed using L-Cys / UIO-66 prepared in Example 1, following these steps:
[0054] Accurately weigh 2 mg of the L-Cys / UIO-66 powder prepared in Example 1 and disperse it in 400 mL of ultrapure water to prepare a solution with a concentration of 5.0 μg / mL. -1 The probe suspension was prepared by adding L-Cys / UIO-66 solution, and its fluorescence emission spectrum was measured. The emission peak intensity at the optimal excitation wavelength (330 nm) was recorded as F0. Next, 15 mmol L-Cys / UIO-66 solution was prepared. -1Aqueous solutions of amino acids with different configurations (L- and D-) (histidine, proline, phenylalanine, α-alanine, isoleucine, tryptophan, threonine, serine, glutamine) were prepared. 3.0 mL of the prepared probe solution was mixed with 20 μL of aqueous solutions of amino acids with different configurations. After standing for 1.0 min, the fluorescence emission spectra of the mixed solution were measured at the optimal excitation wavelength and denoted 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) was used as the metric. R =F2 / F1) is used as an evaluation index for chiral recognition selectivity to evaluate the chiral selectivity of L-Cys / UIO-66 for amino acid enantiomers. Figure 4 As shown, L-Cys / UIO-66 exhibited weak fluorescence responses (F1 / F0 or F2 / F0≈1.0) to the enantiomers of eight amino acids (histidine, proline, phenylalanine, α-alanine, isoleucine, tryptophan, threonine, and serine), while showing the best chiral recognition effect for D / L-Gln (Q...). R =0.87) is lower than that of the other eight amino acids (Q). R ≈1.0).
[0055] The above content demonstrates that the L-Cys / UIO-66 prepared in Example 1 can specifically distinguish between D- and L-Gln, and can perform quantitative analysis of D-Gln.
[0056] Application Example 2: The fluorescence spectrum of the optimal contact time of D-Gln was detected using L-Cys / UIO-66 prepared in Example 1, and the following steps were performed:
[0057] Accurately weigh 2 mg of the L-Cys / UIO-66 powder prepared in Example 1 and disperse it in 400 mL of ultrapure water to prepare a solution with a concentration of 5.0 μg / mL. -1 The probe suspension was obtained by mixing 3.0 mL of the probe solution with 20 μL of D-Gln solution (75.0 mmol / L). -1 Mix thoroughly. At different contact times (0.50 min, 1.0 min, 1.5 min, 2.0 min, 2.5 min, 3.0 min), 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 optimal contact time was determined using the fluorescence intensity ratio F / F0 as the evaluation index. Results are as follows... Figure 5 As shown, 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 results indicate that the L-Cys / UIO-66 prepared in Example 1 can achieve rapid detection of D-Gln.
[0059] Application Example 3: The fluorescence spectrum of D-Gln within its applicable pH range was detected using L-Cys / UIO-66 prepared in Example 1, following these steps:
[0060] Using 1.0 mol L -1 NaOH solution and 1.0 mol L -1 L-Cys / UIO-66 solutions (5.0 μg / mL) with different pH values (4.0, 5.0, 6.0, 7.0, 8.0, 9.0, 10.0) were prepared using HCl solution. -1 The probe solutions with different pH values were mixed with D-Gln (75 mmol / L). -1 Mix well, let stand for 1.0 min, and measure the fluorescence spectrum according to the fluorescence measurement method in Application Example 1, recording the maximum emission peak intensity F. Determine the applicable pH range for the chiral fluorescent probe to detect D-Gln based on F / F0. Results are as follows: Figure 6 As shown, the fluorescence intensity ratio F / F0 of D-Gln to L-Cys / UIO-66 remained essentially unchanged at pH = 6.0-10.0, indicating that L-Cys / UIO-66 can stably recognize D-Gln within the pH range of 6.0-10.0.
[0061] The above results indicate that the L-Cys / UIO-66 prepared in Example 1 has a wide applicable pH range for D-Gln detection, which is beneficial for practical applications.
[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 the L-Cys / UIO-66 powder prepared in Example 1 and disperse it in 400 mL of ultrapure water to prepare a solution with a concentration of 5.0 μg / mL. -1 The probe suspension was obtained by adding L-Cys / UIO-66 solution; 3.0 mL of the probe solution was then mixed with 20 μL of solution containing concentrations ranging from 3.0 to 75.0 mmol / L. -1 The D-Gln solution was mixed thoroughly and allowed to stand for 1.0 min. The fluorescence spectrum was then measured according to the fluorescence measurement method described in Application Example 1, and the maximum emission peak intensity F was recorded. A standard curve was constructed with D-Gln concentration on the x-axis and the fluorescence intensity ratio F / F0 on the y-axis. The results are shown in Figure 7. As the D-Gln concentration increased, the fluorescence intensity of the mixed solution at the maximum emission peak gradually decreased. The fluorescence intensity ratio F / F0 and D-Gln concentration ranged from 20 to 500 μmol / L. -1A good linear relationship was observed within the concentration range, with the linear equation being F / F0 = 0.001081[Gln] + 0.01929, R 2 =0.99807, detection limit is 4.82 μmol L. -1 .
[0064] The above results demonstrate that the L-Cys / UIO-66 prepared in Example 1 can sensitively detect D-Gln.
Claims
1. A method for preparing a rapid enantiomeric fluorescent probe for identifying glutamine, characterized in that... The preparation method is specifically carried out according to the following steps: I. Preparation of amination-modified UIO-66: Zirconium tetrachloride and 2-amino-1,4-phthalic acid were dissolved in N,N-dimethylformamide to obtain a mixed solution. The mixed solution was transferred to a Teflon-lined reactor, and the reactor was placed in a hydrothermal reaction at a temperature of 120℃~130℃ to obtain the reaction product. The reaction product was centrifuged, the solid material was collected, and the collected solid material was washed and vacuum dried to obtain aminated UIO-66. II. Preparation of L-Cys / UIO-66: Aminated UIO-66 and L-cysteine were added to N,N-dimethylformamide, dissolved by sonication, sealed, and reacted at 120℃~130℃ for 22h~26h. After the reaction was completed, the mixture was cooled to room temperature, centrifuged, and the solid material generated in the reaction system was collected. The solid material was washed and vacuum dried to obtain L-Cys / UIO-66, which is the rapid recognition of glutamine enantiomer fluorescent probe. The molar ratio of amino-treated UIO-66 to L-cysteine in step two is 1:(7~9).
2. The method for preparing a rapid glutamine enantiomer fluorescent probe according to claim 1, characterized in that... The mass ratio of zirconium tetrachloride to 2-amino-1,4-phthalic acid in step one is (40~50):(30~40); the mass ratio of zirconium tetrachloride to N,N-dimethylformamide in step one is (40mg~50mg):(20mL~30mL).
3. The method for preparing a rapid glutamine enantiomer fluorescent probe according to claim 1, characterized in that... The hydrothermal reaction time described in step one is 10-12 hours.
4. The method for preparing a rapid glutamine enantiomer fluorescent probe according to claim 1, characterized in that... The centrifugation speed in step one is 6000 rpm to 8000 rpm, and the centrifugation time is 5 min to 8 min.
5. The method for preparing a rapid glutamine enantiomer fluorescent probe according to claim 1, characterized in that... In step one, the collected solid material is washed 3 to 5 times with N,N-dimethylformamide and methanol respectively; the vacuum drying temperature in step one is 60℃ to 80℃, and the vacuum drying time is 10h to 12h.
6. The method for preparing a rapid glutamine enantiomer fluorescent probe according to claim 1, characterized in that... The mass ratio of aminoated UIO-66 to N,N-dimethylformamide in step two is (30mg~50mg):3mL.
7. The method for preparing a rapid glutamine enantiomer fluorescent probe according to claim 1, characterized in that... The centrifugation speed in step two is 6000 rpm to 8000 rpm, and the centrifugation time is 5 min to 8 min.
8. The method for preparing a rapid glutamine enantiomer fluorescent probe according to claim 1, characterized in that... In step two, the solid material is washed 3 to 5 times with N,N-dimethylformamide and methanol respectively; the vacuum drying temperature in step two is 60℃ to 80℃, and the vacuum drying time is 10h to 12h.
9. The application of a rapid identification fluorescent probe for glutamine enantiomers prepared by the preparation method according to claim 1, characterized in that... Application of a rapid fluorescent probe for identifying glutamine enantiomers in glutamine enantiomer fluorescence recognition.