CN115015339A - Preparation method of chiral sensor based on cyclodextrin-based MOF and application of chiral sensor to electrochemical recognition of tryptophan enantiomer - Google Patents

Preparation method of chiral sensor based on cyclodextrin-based MOF and application of chiral sensor to electrochemical recognition of tryptophan enantiomer Download PDF

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CN115015339A
CN115015339A CN202210459403.7A CN202210459403A CN115015339A CN 115015339 A CN115015339 A CN 115015339A CN 202210459403 A CN202210459403 A CN 202210459403A CN 115015339 A CN115015339 A CN 115015339A
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mof
cyclodextrin
chiral
tryptophan
electrode
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杨光
吴小亮
纪捷
李光耀
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Northeast Forestry University
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Abstract

The invention discloses a chiral sensor based on cyclodextrin MOF, a preparation method thereof and electrochemical identification of tryptophan enantiomer, belonging to the technical field of electrochemical sensing. The invention solves the problems of lower sensitivity, weaker peak current, smaller current difference between target chiral molecules and the like of the existing electrochemical sensor based on cyclodextrin. The invention is based on beta-cyclodextrin and K + The CD-MOF is synthesized, chiral recognition of tryptophan enantiomers is realized by utilizing the high porosity and chiral selection center of the CD-MOF, and carbon black nanoparticles and the CD-MOF are assembled on the surface of a glassy carbon electrode in a layered manner, so that the high conductivity capability of Carbon Black (CB) is integrated, and a high-efficiency chiral recognition electrode GCE/CB/CD-MOF is constructed. The differential pulse voltammetry oxidation peak current difference of the system for identifying tryptophan enantiomer can reach 36 muA. Meanwhile, the electrode can also accurately predict the consumption of D-tryptophan and L-tryptophan outside the electrodeThe proportion of the spiro compound.

Description

Preparation method of chiral sensor based on cyclodextrin-based MOF and application of chiral sensor to electrochemical recognition of tryptophan enantiomer
Technical Field
The invention relates to a preparation method of a chiral sensor based on a cyclodextrin-based Metal Organic Framework (MOF) and application of the chiral sensor to electrochemical recognition of tryptophan enantiomers, and belongs to the technical field of electrochemical sensing.
Background
Tryptophan as a second essential amino acid plays a crucial role in biological activity or pharmacological behavior, and its L-and D-isomers have different effects on the human body, so it is becoming more and more important to develop a simple and efficient method for identifying tryptophan enantiomers. The electrochemical method has the advantages of low cost, simplicity, rapid analysis, high sensitivity, high selectivity and the like, and is widely concerned in the field of chiral tryptophan recognition.
The cyclodextrin is the most common chiral hole selector in the electrochemical chiral sensor, can provide a good host chiral environment for the identification of chiral tryptophan molecules, and is commonly used for constructing the electrochemical chiral sensor. However, due to the insulating property of cyclodextrin, the current electrochemical sensor based on cyclodextrin has low sensitivity, weak peak current and small current difference between target chiral molecules, and is difficult to perform accurate quantitative analysis on chiral substances and determine single components in an enantiomer mixture.
Therefore, it is necessary to provide an electrochemical sensor capable of efficiently recognizing the tryptophan enantiomer and capable of predicting the proportion of D-tryptophan and L-tryptophan in the racemate thereof with occasional accuracy.
Disclosure of Invention
The invention provides a preparation method of an electrode material based on cyclodextrin matrix MOF and application of the electrode material to electrochemical recognition of tryptophan enantiomers, aiming at solving the problems of low sensitivity, weak peak current, small current difference between target chiral molecules and the like of the existing electrochemical sensor based on cyclodextrin.
The technical scheme of the invention is as follows:
a preparation method of chiral sensors based on cyclodextrin MOF comprises the following implementation steps:
s1, preparing cyclodextrin-based metal organic framework material CD-MOF;
s2, preparing a carbon black modified glassy carbon electrode GCE/CB;
s3, mixing the CD-MOF and ultrapure water to obtain a suspension, then dripping the suspension on the surface of GCE/CB, and drying under infrared light to obtain the chiral sensor GCE/CB/CD-MOF based on the cyclodextrin-based MOF.
Further, the operation procedure of S1 is: putting beta-cyclodextrin and KOH into water, performing ultrasonic dissolution, filtering by using a filter, transferring the filtrate into a closed container containing methanol, standing for 3 days at 50 ℃, filtering, washing precipitated crystals by using methanol, and drying at 50 ℃ under vacuum to obtain the CD-MOF.
More particularly, the molar ratio of beta-cyclodextrin to KOH is 1: 8.
further, the operation procedure of S2 is:
(1) polishing the glassy carbon electrode by using alumina slurry, then washing the glassy carbon electrode by using ultrapure water, ethanol and ultrapure water in sequence, and drying the glassy carbon electrode under an infrared lamp to obtain a pretreated glassy carbon electrode;
(2) dispersing carbon black in methanol, performing ultrasonic treatment to obtain a uniform suspension, dripping the suspension on the surface of the pretreated glassy carbon electrode, and drying under infrared light to obtain GCE/CB.
More specifically, the concentration of the suspension in step (2) is 3.0 mg/mL.
Further, the operation procedure of S3 is:
dissolving 5.0mg of CD-MOF in 1.0mL of ultrapure water, carrying out ultrasonic treatment to obtain a 5.0mg/mL colorless and transparent CD-MOF aqueous solution, dripping 5 mu L of CD-MOF solution on the surface of GCE/CB, and drying under infrared light to obtain GCE/CB/CD-MOF
The invention also provides a chiral sensor based on the cyclodextrin MOF, which is prepared by applying the preparation method.
The invention also provides application of the chiral sensor based on the cyclodextrin MOF, and the chiral sensor is particularly used for electrochemical recognition of tryptophan enantiomers.
Further limiting, immersing the chiral sensor based on cyclodextrin-based MOF in 50mL of 0.1moL/L PBS (pH range of 7.0) containing 5mmoL/L L-or D-Trp for 30s, and then performing chiral recognition on tryptophan enantiomer by using Differential Pulse Voltammetry (DPV), wherein the differential pulse voltammetry of tryptophan enantiomer oxidizes peak current difference (I) L -I D ) Can reach 36 muA.
Further, the DPV adopts a three-electrode system, the reference electrode is an Ag/AgCl electrode, and the counter electrode is a Pt sheet electrode.
Further limited, the temperature of the differential pulse voltammetry DPV test is 25 ℃, the voltage range is +0.4 to +1.2V, the pulse amplitude is 0.05V, the pulse width is 0.06s, the sample width is 0.02s, the pulse period is 0.5s, the rest time is 2s, and the scan rate is 0.004V/s.
The invention also provides an application of the chiral sensor based on the cyclodextrin-based MOF, and the chiral sensor is particularly used for quantitative analysis of tryptophan enantiomers.
Further defined, the chiral sensor based on cyclodextrin-based MOF was immersed for 30s in 50mL of 0.1moL/L PBS (pH range 7.0) containing 2, 3, 4, 5, 6, L L-Trp or D-Trp for quantitative analysis of tryptophan enantiomers using differential pulse voltammetry DPV.
Further, the DPV adopts a three-electrode system, the reference electrode is an Ag/AgCl electrode, and the counter electrode is a Pt sheet electrode.
Further limiting, the temperature of the differential pulse voltammetry DPV test is 25 ℃, the voltage range is +0.4 to +1.2V, the pulse amplitude is 0.05V, the pulse width is 0.06s, the sample width is 0.02s, the pulse period is 0.5s, the rest time is 2s, and the scanning rate is 0.004V/s.
The invention also provides an application of the chiral sensor based on the cyclodextrin-based MOF, and the chiral sensor is particularly used for quantitative analysis of D-Trp in a tryptophan enantiomer mixture.
Further defined, the chiral sensor based on cyclodextrin-based MOF was immersed for 30s in 50mL of 0.1moL/L PBS (pH range 7.0) containing 0%, 20%, 40%, 60%, 80%, 100% (total concentration 5mmoL/L) of D-Trp, and then quantitative analysis of D-Trp in the mixture of tryptophan enantiomers was performed using differential pulse voltammetry DPV.
Further, the DPV adopts a three-electrode system, the reference electrode is an Ag/AgCl electrode, and the counter electrode is a Pt sheet electrode.
Further limited, the temperature of the differential pulse voltammetry DPV test is 25 ℃, the voltage range is +0.4 to +1.2V, the pulse amplitude is 0.05V, the pulse width is 0.06s, the sample width is 0.02s, the pulse period is 0.5s, the rest time is 2s, and the scan rate is 0.004V/s.
The invention is based on beta-cyclodextrin and K + A green renewable metal organic framework material, namely CD-MOF, is synthesized, and chiral recognition is realized on tryptophan enantiomers by utilizing the high porosity and chiral selection center of the CD-MOF. Meanwhile, carbon black nanoparticles and CD-MOF are assembled on the surface of the glassy carbon electrode in a layered mode, the high conductivity of CB and the chiral selection capability of CD-MOF are integrated, and a high-efficiency chiral recognition electrode GCE/CB/CD-MOF is constructed, and compared with the prior art, the method has the following specific beneficial effects:
(1) the invention constructs a high-efficiency chiral recognition electrode GCE/CB/CD-MOF by utilizing the high porosity of the cyclodextrin-based MOF and the high conductivity of carbon black nano particles, so that the system recognizes the differential pulse voltammetry oxidation peak current difference (I) of tryptophan enantiomer L -I D ) Can reach 36 muA.
(2) Meanwhile, the electrode provided by the invention can accurately predict the proportion of D-tryptophan and L-tryptophan in the racemate thereof.
(3) In addition, the electrode material provided by the invention has the advantages of simple preparation process, excellent chiral recognition capability, simple and convenient electrochemical recognition operation process, strong operability, strong environmental interference resistance, sensitive and quick system response and the like.
Drawings
FIG. 1 is a synthetic scheme for preparing CD-MOF according to the present invention;
FIG. 2 is an XRD spectrum of CD-MOF;
FIG. 3 is an infrared spectrum of β -CD and CD-MOF;
FIG. 4 is a scanning electron microscope image of CD-MOF;
FIG. 5 is a graph showing the results of chiral tryptophan recognition by GCE/CB/CD-MOF;
FIG. 6 is a schematic diagram of the GCE/CB/CD-MOF chiral tryptophan recognition scheme;
FIG. 7 is a calibration graph of GCE/CB/CD-MOF peak current versus Trp concentration;
FIG. 8 is a diagram showing the quantitative analysis of D-Trp in a mixture of tryptophan enantiomers by GCE/CB/CD-MOF.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and do not limit the invention.
The experimental procedures used in the following examples are conventional unless otherwise specified. The materials, reagents, methods and apparatus used, unless otherwise specified, are conventional in the art and are commercially available to those skilled in the art.
Example 1:
the preparation method of the sensor based on the cyclodextrin-based MOF electrode material comprises the following specific steps:
preparing cyclodextrin-based metal organic framework material CD-MOF:
as shown in FIG. 1, β -CD (0.586g, 0.5mmol) and KOH (0.224g, 4mmol) were dissolved in H 2 In O (20mL), dissolve with sonication. After filtration through a 0.45 μm filter, the above solution was transferred to a closed glass bottle, 25mL of methanol was added to the bottle, and the bottle was placed in a 50 ℃ forced air drying oven and allowed to stand for reaction for 3 days, whereby methanol vapor was slowly diffused in the solution, and it was observed that transparent colorless crystals appeared on the bottom and wall of the glass bottle. After filtration, the crystals were washed three times with methanol and finally dried overnight under vacuum at 50 ℃ and the colorless CD-MOF crystals were collected.
The CD-MOF is characterized, an XRD spectrogram is shown in figure 2, the crystallinity of the CD-MOF is high, and the crystallinity and X-ray powder diffraction peaks of the CD-MOF are respectively 6.4 degrees, 9.0 degrees, 12.7 degrees and 18.7 degrees, which preliminarily shows that the CD-MOF is successfully synthesized. The IR spectrum of CD-MOF is shown in FIG. 3, and the characteristic peaks of beta-CD appear at 3400cm -1 (-OH stretching vibration), 2927cm -1 (-OH stretching vibration) 1080cm -1 (C-O-C stretching vibration) and 1028cm -1 (C-O stretching vibration); the FT-IR spectrum of the CD-MOF shows characteristic peaks consistent with beta-CD, which indicates that-OH and beta-CD characteristics in the CD-MOF are still retained,OH, C-O-C, C-O groups, from which the successful synthesis of CD-MOF can be concluded. A scanning electron microscope image of the CD-MOF is shown in FIG. 4, and the prepared CD-MOF is in a block-rectangular shape with different sizes, and the size distribution of the CD-MOF is wide and ranges from 20 micrometers to 100 micrometers.
(II) preparing a carbon black modified glassy carbon electrode GCE/CB:
polishing GCE with 0.05um alumina slurry for about 2 minutes, then washing with ultrapure water, ethanol and ultrapure water in sequence, and drying under an infrared lamp. 3.0mg CB was dispersed in 1.0mL methanol and sonicated to give a uniform 3.0mg/mL suspension. Dripping 3 mu L of CB solution on the surface of GCE, and drying under infrared light to obtain the modified electrode GCE/CB.
(III) preparing a chiral sensor GCE/CB/CD-MOF based on cyclodextrin base MOF:
5.0mg of CD-MOF was dissolved in 1.0mL of ultrapure water and sonicated to give a 5.0mg/mL colorless and transparent aqueous solution of CD-MOF. Dripping 5 mu L of CD-MOF solution on the surface of GCE/CB, and drying under infrared light to obtain GCE/CB/CD-MOF.
Example 2:
the electrochemical identification of tryptophan enantiomers based on a cyclodextrin-based MOF electrode material sensor comprises the following specific processes:
soaking a GCE/CB/CD-MOF electrode in 50mL of 0.1mol/L PBS buffer solution (pH range is 7.0) containing 5mmol/L L-Trp or D-Trp for 30s, and then performing chiral recognition on a tryptophan enantiomer by using a Differential Pulse Voltammetry (DPV) which adopts a three-electrode system, wherein the reference electrode is an Ag/AgCl electrode, the counter electrode is a Pt plate electrode, the temperature for testing the DPV is 25 ℃, the voltage range is +0.4 to +1.2V, the pulse amplitude is 0.05V, the pulse width is 0.06s, the sample width is 0.02s, the pulse period is 0.5s, the rest time is 2s, and the scanning rate is 0.004V/s. The results are shown in FIG. 5, where differential pulse voltammetry oxidation of tryptophan enantiomers peak current difference (I) L -I D ) Up to 36 μ a, which may be explained by CB enhancing the electrical activity of Trp oxidation, CD-MOF providing the lumenal chiral selection center of β -CD, and furthermore the high porosity and specific surface area of CD-MOF facilitating the binding of more amino acid enantiomers to the sensor. FIG. 6 shows modified electricityThe scheme for identifying tryptophan by extreme chirality can speculate that the mechanism for identifying the tryptophan enantiomer is as follows: due to the higher affinity of the CD-MOF to the D-Trp, the D-Trp is more difficult to pass through the CD-MOF membrane to reach the electrode surface for oxidation, so that the peak current of the D-Trp is lower than that of the L-Trp.
And (II) respectively soaking the GCE/CB/CD-MOF electrode in 50mL of 0.1mol/L PBS buffer solution (pH range is 7.0) containing 2mmol/L (a), 3mmol/L (b), 4mmol/L (c), 5mmol/L (D), 6mmol/L (e) L-Trp or D-Trp for 30s, and carrying out quantitative analysis on the tryptophan enantiomer by using Differential Pulse Voltammetry (DPV), wherein the Differential Pulse Voltammetry (DPV) adopts a three-electrode system, the reference electrode is an Ag/AgCl electrode, the counter electrode is a Pt sheet electrode, the temperature of the Differential Pulse Voltammetry (DPV) test is 25 ℃, the voltage range is +0.4 to +1.2V, the pulse amplitude is 0.05V, the pulse width is 0.06s, the sample width is 0.02s, the pulse period is 0.5s, the resting time is 2s, and the scanning rate is 0.004V/s. As shown in FIG. 7, the peak current was in a linear relationship with the concentrations of L-Trp and D-Trp in the range of 2 to 6mmol/L (a to e), and the detection limits of L-Trp and D-Trp were 0.54. mu.M and 1.46. mu.M, respectively (S/N: 3); the linear equation is: ip (μ a) ═ 14.41C L-Trp (mM)+95.59(R 2 ＝0.994)，Ip(μA)＝5.59C D-Trp (mM)+100.54(R 2 ＝0.993)。
And (III) respectively soaking the GCE/CB/CD-MOF electrodes into 50mL of 0.1mol/L PBS buffer solution (the pH range is 7.0) containing 0%, 20%, 40%, 60%, 80% and 100% (the total concentration is 5mmol/L) of D-Trp for 30s, and carrying out quantitative analysis on the D-Trp in the tryptophan enantiomer mixture by using differential pulse voltammetry DPV, wherein the differential pulse voltammetry DPV adopts a three-electrode system, the reference electrode is an Ag/AgCl electrode, the counter electrode is a Pt sheet electrode, the temperature for testing the differential pulse voltammetry DPV is 25 ℃, the voltage range is +0.4 to +1.2V, the pulse amplitude is 0.05V, the pulse width is 0.06s, the sample width is 0.02s, the pulse period is 0.5s, the resting time is 2s, and the scanning rate is 0.004V/s. As a result, as shown in FIG. 8, the DPV curves of the D-Trp enantiomer solutions at different fixed ratios exhibited a single oxidation peak, and the peak current decreased as the concentration of D-Trp increased (from 0 to 100% of D-Trp%). And it can be observed that there is good linearity between the peak current and the percentage of D-Trp contentThe relationship is as follows: ip (μ a) ═ 0.35D-Trp% +166.12 (R) 2 0.994), which indicates that the percentage of one enantiomer can be predicted accurately based on GCE/CB/CD-MOF.
The above embodiments are merely preferred embodiments of the present invention, and the present invention is not limited to the above embodiments, and modifications and changes thereof may be made by those skilled in the art within the scope of the claims of the present invention.

Claims (10)

1. A preparation method of chiral sensors based on cyclodextrin MOF is characterized by comprising the following steps:
s1, preparing cyclodextrin-based metal organic framework material CD-MOF;
s2, preparing a carbon black modified glassy carbon electrode GCE/CB;
s3, mixing the CD-MOF with ultrapure water to obtain a suspension, then dripping the suspension on the surface of GCE/CB, and drying under infrared light to obtain the chiral sensor GCE/CB/CD-MOF based on the cyclodextrin-based MOF.
2. The method for preparing the cyclodextrin-based MOF electrode material according to claim 1, wherein the operation of S1 is as follows: putting beta-cyclodextrin and KOH into water, performing ultrasonic dissolution, filtering by using a filter, transferring the filtrate into a closed container containing methanol, standing for 3 days at 50 ℃, filtering, washing precipitated crystals by using methanol, and drying at 50 ℃ under vacuum to obtain the CD-MOF.
3. The method of preparing a cyclodextrin-based MOF electrode material according to claim 2, wherein the molar ratio of β -cyclodextrin to KOH is 1: 8.
4. the method for preparing the cyclodextrin-based MOF electrode material according to claim 1, wherein the operation of S2 is as follows:
(1) polishing the glassy carbon electrode by using alumina slurry, then washing by using ultrapure water, ethanol and ultrapure water in sequence, and drying under an infrared lamp to obtain the pretreated glassy carbon electrode;
(2) dispersing carbon black in methanol, performing ultrasonic treatment to obtain a uniform suspension, dripping the suspension on the surface of the pretreated glassy carbon electrode, and drying under infrared light to obtain GCE/CB.
5. A chiral sensor based on cyclodextrin MOF, which is prepared by the method of claim 1.
6. Use of the chiral sensor of claim 5 for electrochemical recognition of tryptophan enantiomers.
7. The use of the chiral sensor based on cyclodextrin MOF according to claim 6, wherein GCE/CB/CD-MOF is soaked in PBS buffer solution containing L-tryptophan (L-Trp) or D-tryptophan (D-Trp) and differential pulse voltammetry is used for chiral recognition.
8. Use of the chiral sensor of claim 5 for the quantitative analysis of tryptophan enantiomers.
9. The use of chiral sensors based on cyclodextrin MOFs according to claim 8, wherein GCE/CB/CD-MOFs are immersed in PBS buffer solutions containing different concentrations of L-Trp or D-Trp and tryptophan enantiomers are quantitatively analyzed by differential pulse voltammetry.
10. Use of the chiral sensor of claim 5 for the quantitative analysis of D-Trp in a mixture of tryptophan enantiomers.
CN202210459403.7A 2022-04-24 2022-04-24 Preparation method of chiral sensor based on cyclodextrin-based MOF and application of chiral sensor to electrochemical recognition of tryptophan enantiomer Pending CN115015339A (en)

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