CN113125547A - Chiral compound detection method - Google Patents
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- CN113125547A CN113125547A CN202010045747.4A CN202010045747A CN113125547A CN 113125547 A CN113125547 A CN 113125547A CN 202010045747 A CN202010045747 A CN 202010045747A CN 113125547 A CN113125547 A CN 113125547A
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- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/72—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating magnetic variables
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/1717—Systems in which incident light is modified in accordance with the properties of the material investigated with a modulation of one or more physical properties of the sample during the optical investigation, e.g. electro-reflectance
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01R—MEASURING ELECTRIC VARIABLES; MEASURING MAGNETIC VARIABLES
- G01R33/00—Arrangements or instruments for measuring magnetic variables
- G01R33/02—Measuring direction or magnitude of magnetic fields or magnetic flux
- G01R33/032—Measuring direction or magnitude of magnetic fields or magnetic flux using magneto-optic devices, e.g. Faraday or Cotton-Mouton effect
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/1717—Systems in which incident light is modified in accordance with the properties of the material investigated with a modulation of one or more physical properties of the sample during the optical investigation, e.g. electro-reflectance
- G01N2021/1727—Magnetomodulation
Abstract
The invention provides a method for detecting a chiral compound, which is characterized in that a chiral photomagnetic response material is adopted as a substrate material to be matched with a gaussmeter so as to detect the chiral compound, and the method comprises the following steps: step S1, placing a sample to be tested of the chiral compound on a substrate material; and step S2, irradiating the sample to be detected with laser, and detecting the magnetic field intensity generated after the sample to be detected is irradiated with the laser by using a gauss meter so as to obtain a detection result, wherein the laser irradiating the sample to be detected is unpolarized light. Compared with the chiral compound detection method in the prior art, the detection method has the advantages of simple operation, accurate result, easy realization of field detection and the like.
Description
Technical Field
The invention relates to a detection method of a chiral compound.
Background
The chiral compound refers to a class of compounds with the same molecular structure but the configurations are mirror images of each other. In the pharmaceutical and chemical field, a pair of chiral compounds which are mirror images of each other usually have different characteristics, for example, thalidomide has two enantiomeric configurations of S and R which are mirror images of each other, wherein R has a central sedative effect, and S has a strong teratogenic effect. Therefore, the separation between enantiomers and the detection of the content are crucial steps in the development and production process of chiral compounds.
In the prior art, methods for analyzing and detecting chiral compounds mainly include two types, namely spectra and chromatograms. The spectral method is often realized by utilizing the optical rotation of a chiral compound (i.e., the property of deflecting polarized light), and is difficult to quantify and susceptible to stray light interference. And the spectroscopy requires very precise optics, which presents a significant challenge to the fabrication process. The chromatographic method mainly depends on the difference of the adsorption capacity of chromatographic column packing on chiral compounds with different configurations for separation and content detection, however, the applicable range of the chromatographic method is limited, the common chiral chromatographic column can only be applied to a part of chiral compounds which accord with the adsorption characteristics of the chiral chromatographic column, and compounds with overlarge molecular weight, undersize molecular weight or no polarity can not be detected. In addition, the devices required for chromatographic methods are generally bulky and inconvenient to carry, and thus field detection of samples is difficult to achieve.
Disclosure of Invention
In order to solve the above problems, the inventors of the present invention have conducted studies on the physical properties of chiral compounds, and found that the chiral compounds exhibit the following properties under light irradiation: when the chiral molecules are subjected to magnetic field detection by adopting the chiral photomagnetic responsive material as a substrate material, the detection result is different along with the content change of the enantiomer. Moreover, the inventor also finds that the intensity change and the content of the enantiomer accord with a linear rule, so that the content proportion can be calculated according to the detection result of the magnetic field intensity corresponding to the loaded enantiomers with different content proportions, and the chiral compound can be detected.
Based on the above findings, the inventors propose a method for detecting a chiral compound, specifically adopting the following technical scheme:
the invention provides a method for detecting a chiral compound, which is characterized in that a chiral photomagnetic response material is adopted as a substrate material to be matched with a gaussmeter so as to detect the chiral compound, and the method comprises the following steps: step S1, placing a sample to be tested of the chiral compound on a substrate material; and step S2, irradiating the sample to be detected with laser, and detecting the magnetic field intensity generated after the sample to be detected is irradiated with the laser by using a gauss meter so as to obtain a detection result, wherein the laser irradiating the sample to be detected is unpolarized light.
Further, the method for detecting a chiral compound provided by the present invention may further have a technical feature that the photo-magnetically responsive material having chirality in step S1 is one or a mixture of several of a metal nano-spiral line array, a composite metal nano-spiral line array, a metal oxide nano-spiral line array, and a composite metal oxide nano-spiral line array.
Further, the detection method of the chiral compound provided by the invention can also comprise the following steps: and step S3, analyzing the magnetic field intensity detected in the step S2 to obtain the content of the enantiomer in the chiral compound.
Further, in the method for detecting a chiral compound provided by the present invention, the analysis in step S3 may include the following steps: s3-1, preparing a plurality of chiral compound standards, wherein each standard contains enantiomers of chiral compounds with different amounts; s3-2, respectively placing each standard product on a substrate material, respectively irradiating by laser and detecting the magnetic field intensity generated after the laser irradiates the sample to be detected by a Gauss meter, thereby obtaining the magnetic field intensity generated after the irradiation of each standard product; and step S3-3, comparing and analyzing the magnetic field strengths of the standard sample and the sample to be detected to obtain the enantiomer content of the chiral compound in the sample to be detected.
Furthermore, in the detection method of the chiral compound provided by the present invention, the comparative analysis in step S3-3 may be: and drawing a standard curve according to the relationship between the magnetic field strength of the standard substance and the enantiomer content, and obtaining the enantiomer content of the chiral compound according to the standard curve and the magnetic field strength of the sample to be detected.
Action and Effect of the invention
According to the detection method of the chiral compound provided by the invention, as the photo-magnetic response material with chirality is adopted as the substrate material during magnetic field detection, the photo-magnetic response material can generate magnetic fields with different intensities according to the difference of the chiral compounds, and the chiral compounds which are antipodal to each other can generate magnetic fields with obviously different intensities, so that the content proportion can be calculated by measuring the magnetic field intensity through a gauss meter, thereby realizing the detection of the chiral compounds. Compared with the chiral compound detection method in the prior art, the detection method has the advantages of simple operation, accurate result, easy realization of field detection and the like.
Drawings
FIG. 1 is a scanning electron micrograph of an R-type gold nanospiral array according to a first embodiment of the present invention;
FIG. 2 is a low power transmission electron micrograph of an R-type gold nanospiral array according to a first embodiment of the present invention;
FIG. 3 is a high-power TEM image of the R-type Au nanospiral array according to the first embodiment of the present invention;
FIG. 4 is a circular dichroism spectrum of a gold nanospiral array according to a first embodiment of the present invention;
FIG. 5 is a flow chart of a method for detecting a chiral compound according to example one of the present invention;
FIG. 6 is a plot of the magnetic field strength as a linear fit to the percentage of chiral molecules present in a mixture of N-acetyl-L-cysteine and N-acetyl-D-cysteine using a Gauss meter using the detection method of example one of the present invention;
FIG. 7 is a plot of the magnetic field strength as a linear fit to the percentage of chiral molecule content using a gauss meter for a mixture of S-1-phenyl-1, 2-ethanediol and R-1-phenyl-1, 2-ethanediol as determined by the method of example one of the present invention.
Detailed Description
The following describes embodiments of the present invention with reference to the drawings.
< example one >
In the embodiment, the gold nano spiral array is adopted as a photo-magnetic response material with chirality to detect the chiral compound.
The gold nano spiral array is prepared by the following preparation method:
step S0-1, placing the substrate into an amino silanization reagent, standing for a period of time, taking out and washing;
step S0-2, soaking the substrate washed in the step S0-1 into a solution containing metal species so as to load the metal species;
step S0-3, placing the substrate loaded with the metal seeds into a mixed solution containing a metal source and an inducer, adding a reducing agent to carry out growth reaction for a preset time, and growing a metal spiral line array on the substrate to obtain a metal spiral line array plate, wherein the inducer is a chiral inducer;
and step S0-4, removing the residual inducer in the metal spiral line array plate.
In the above process, the substrate used in step S0-1 is a silicon substrate that has been previously cleaned in the following manner: the silicon substrate is put into a mixed solution containing concentrated sulfuric acid and hydrogen peroxide (the volume ratio of the concentrated sulfuric acid to the hydrogen peroxide is 3:1) and heated for 2 hours at 60 ℃, then is subjected to ultrasonic treatment for half an hour, and then is taken out and washed with deionized water for three times.
The aminosilane reagent used in step S0-1 was a 5mM solution of 3-aminopropyltriethoxysilane, and the standing time was 2 hours.
The metal seeds of the step S0-2 are gold seeds, and the soaking time is 2 hours.
The metal source of the step S0-3 is chloroauric acid, the inducer is chiral inducer N-acetyl-L-cysteine, and the reducing agent is ascorbic acid. Specifically, the mixed solution of the inducer and the reducing agent contains 3.45mM of chiral inducer (N-acetyl-L-cysteine or N-acetyl-D-cysteine), 2.76mM of 4-mercaptobenzoic acid, 8.62mM of chloroauric acid and 20.69mM of ascorbic acid.
The growth reaction of step S0-3 was carried out by standing at room temperature for a predetermined time of 15 minutes. In addition, in step S0-3, the metal helix array sheet is obtained, washed with absolute ethanol three times, and then dried.
The removal of the residual inducer of step S0-4 employs an electrochemical method, specifically cyclic voltammetry.
In this example, N-acetyl-L cysteine was used as an inducer to prepare an L-type gold nanospiral array, and N-acetyl-D-cysteine was also used as an inducer to prepare an R-type gold nanospiral array.
Fig. 1 is a scanning electron micrograph of an R-type gold nano-spiral array according to a first embodiment of the present invention, fig. 2 is a low-power transmission electron micrograph of the R-type gold nano-spiral array according to a first embodiment of the present invention, and fig. 3 is a high-power transmission electron micrograph of the R-type gold nano-spiral array according to a first embodiment of the present invention.
As can be seen from FIGS. 1 to 3, the R-shaped gold nanospiral array prepared in this example is composed of regularly arranged gold wires, each gold wire has a diameter of about 5nm to 6nm and a length of about 500 μm at the longest. In addition, the L-type gold nano-spiral array presents similar appearance to the images in the electron microscope pictures in figures 1-3, which are not listed here.
Fig. 4 is a circular dichroism spectrum of the gold nano-spiral array according to the first embodiment of the present invention. In FIG. 4, L-CNAF is L-type gold nano-spiral array film, and R-CNAF is R-type gold nano-spiral array film.
As shown in fig. 4, the L-type gold nanospiral array and the R-type gold nanospiral array have obvious circular dichroism, indicating that both have single chirality, respectively.
FIG. 5 is a flow chart of a method for detecting a chiral compound according to a first embodiment of the present invention.
In order to illustrate the effect of the gold nano-spiral array in the detection of chiral compounds, the R-type gold nano-spiral array is used as a photo-magnetic responsive material in the embodiment, and a gauss meter is combined to detect the chiral compounds. That is, a sample to be detected of a chiral compound is prepared into a solution with a proper concentration, the solution is dripped to an R-type gold nano spiral array growing on a silicon substrate, then the silicon substrate is placed under a 514nm laser irradiation condition, and a gauss meter is used for magnetic field strength detection, as shown in fig. 5, the detection method of the embodiment specifically includes the following steps:
step S1, placing a sample to be tested of the chiral compound on a substrate material;
step S2, irradiating the sample by 514nm laser, and detecting the sample to be detected by a gaussmeter so as to obtain the magnetic field intensity of the sample to be detected;
and step S3, analyzing the magnetic field intensity obtained in the step S2 to obtain the content of the enantiomer in the chiral compound.
The 514nm laser beam of step S2 is unpolarized light, that is, generated by a conventional laser generator and directly irradiated onto the sample to be measured, and optical devices capable of polarizing the laser beam are not used.
In addition, in this embodiment, the content of the enantiomer in the sample to be tested is quantified by a standard curve analysis method. Specifically, the analysis process in step S3 further includes the steps of:
s3-1, preparing a plurality of chiral compound standards, wherein each standard contains enantiomers of chiral compounds with different amounts;
s3-2, respectively placing the standard products on the substrate material, respectively irradiating with 514nm laser and detecting the standard products by adopting a Gauss meter so as to obtain the magnetic field intensity corresponding to each standard product;
and step S3-3, comparing and analyzing the magnetic field strengths of the standard sample and the sample to be detected to obtain the enantiomer content of the chiral compound in the sample to be detected.
This example uses N-acetyl-cysteine as the chiral compound to be tested, which has two configurations, N-acetyl-L-cysteine (S-NAC) and N-acetyl-D-cysteine (R-NAC).
FIG. 6 is a plot of magnetic field strength versus percent chiral molecule content using a Gauss meter for a mixture of R-NAC and S-NAC using the detection method of example one of the present invention. In FIG. 6, the abscissa is the percentage of content of chiral molecules (ee value), the ordinate is the magnetic field strength, -100% is a sample containing only R-NAC, 100% is a sample containing only S-NAC, -50% is a sample having a content ratio of R-NAC to S-NAC of 75:25, 0% is a sample having a content ratio of R-NAC to S-NAC of 50:50, and 50% is a sample having a content ratio of R-NAC to S-NAC of 25: 75. In addition, the total content (sum of molar concentrations) of R-NAC and S-NAC was the same in each sample.
As shown in FIG. 6, when the R-type gold nano-spiral array is used for detecting the chiral compound of N-acetyl-cysteine, the magnetic field intensity of the R-type gold nano-spiral array is in a direct proportion relation with the proportion of chiral molecules in a sample. That is to say, when two N-acetyl-cysteine samples with unknown isomer contents need to be detected, the R-type gold nanospiral array of the present embodiment is used as a substrate material to perform magnetic field detection in combination with laser irradiation, and then the detection result is compared with a linear fitting graph formed by a standard product for analysis, so as to calculate the content ratio of R-NAC and S-NAC in the sample to be detected.
< example two >
In this embodiment, the chiral compound is detected by using the same detection method and the substrate material (i.e., R-type gold nano-spiral array) as in the first embodiment. The chiral compound to be detected is 1-phenyl-1, 2-ethanediol and has two configurations, namely S-1-phenyl-1, 2-ethanediol and R-1-phenyl-1, 2-ethanediol.
FIG. 7 shows the magnetic field intensity measured for a mixture of S-1-phenyl-1, 2-ethanediol and R-1-phenyl-1, 2-ethanediol using the measurement method of example one of the present invention. In FIG. 7, - < 100 > is a sample containing only S-1-phenyl-1, 2-ethanediol, 100 > is a sample containing only R-1-phenyl-1, 2-ethanediol, 50 > is a sample containing the ratio of the contents of R-1-phenyl-1, 2-ethanediol and S-1-phenyl-1, 2-ethanediol at 75:25, 0 > is a sample containing the ratio of the contents of R-1-phenyl-1, 2-ethanediol and S-1-phenyl-1, 2-ethanediol at 50:50, and 50 > is a sample containing the ratio of the contents of R-1-phenyl-1, 2-ethanediol and S-1-phenyl-1, 2-ethanediol at 25: 75. The total content (sum of molar concentrations) of S-1-phenyl-1, 2-ethanediol and R-1-phenyl-1, 2-ethanediol was the same for each sample.
As shown in FIG. 7, when the chiral compound 1-phenyl-1, 2-ethanediol is detected by using the R-type gold nano spiral array, the magnetic field intensity is in a direct proportion relation with the chiral molecular proportion in the sample. That is to say, when two samples of 1-phenyl-1, 2-ethanediol with unknown isomer content need to be detected, the R-type gold nanospiral array of the present embodiment is used as a substrate material to perform magnetic field detection, and then the detection result is compared with a linear fitting graph formed by a standard substance, so as to calculate the content ratio of S-1-phenyl-1, 2-ethanediol and R-1-phenyl-1, 2-ethanediol in the sample to be detected.
< example three >
In order to examine whether the gold nano-spiral arrays prepared under different conditions can be applied in the detection method of the present invention, different gold nano-spiral arrays prepared under different conditions are used in the present embodiment, and the gold nano-spiral arrays are used as substrate materials, and magnetic field detection experiments are performed by using the detection method of the first embodiment.
In this example, a total of three gold nanospiral arrays were prepared, which were prepared by the same procedure as in example one, but under different conditions as follows:
the first method comprises the following steps: the dosage of the 4-mercaptobenzoic acid in the step S0-3 is changed to 3.45 mM;
and the second method comprises the following steps: the dosage of the 4-mercaptobenzoic acid in the step S0-3 is changed to 4.14 mM;
and the third is that: in step S0-3, N-acetyl L-cysteine was used in an amount of 2.76mM instead.
When the three gold nano spiral arrays are used for detecting the N-acetyl-cysteine in the first embodiment, the magnetic field intensity of the three gold nano spiral arrays is in a uniform proportional relation with the chiral molecular proportion in the sample, namely, the three gold nano spiral arrays can show the same characteristics as the gold nano spiral array in the first embodiment. In other words, the gold nano helical wire array prepared under different conditions can also be used as a substrate material to be matched with a gaussmeter, so that the content proportion detection of chiral compounds with different configurations can be realized by the detection method of the first embodiment of the invention.
< example four >
In order to verify whether other photo-magnetic responsive materials with chirality can also be used in the detection method of the present invention, the gold-silver nanowire array is prepared and the gold-silver nanowire array is used as a substrate material to perform chiral compound detection.
In this embodiment, the first four steps of the method for preparing gold-silver nanowire arrays are the same as the steps S0-1 to S0-3 of the embodiment. The difference is that after step S0-3, a silver attaching step is performed, specifically as follows:
and (4) placing the gold nano spiral line array obtained in the step (S0-3) into a solution containing 5mM of silver nitrate and 10mM of ascorbic acid, standing for 5 minutes for reaction, taking out, washing with ethanol for three times, and drying to obtain the gold-silver nano spiral line array.
And then, carrying out organic matter removal operation on the dried gold-silver nano spiral line array to obtain the chiral gold-silver nano spiral line array.
Through magnetic field detection experiments, the gold-silver nano spiral array can also show the same characteristics as the gold nano spiral array in the first embodiment. Namely, the gold-silver nano spiral array can also be used as a substrate material to be matched with a gaussmeter, so that the content ratio detection of chiral compounds with different configurations in a sample to be detected is realized.
In addition, the inventors have found that the same test as the above embodiment can be achieved by using other materials having similar characteristics. The materials are all nano metal film materials, nano metal powder materials and nano metal oxide powder materials with a single chiral structure, and when the materials are used as substrate materials for detection, the materials can show the same characteristics as the gold nano spiral array and the gold-silver nano spiral array in the embodiment, so that the materials can be used as the substrate materials to be matched with a Gauss meter, and the content proportion detection of chiral compounds with different configurations in a sample to be detected is realized.
Effects and effects of the embodiments
It can be seen from the above examples that when the chiral photo-magnetic responsive material is used as the substrate material for magnetic field intensity detection, the detection result varies with the content of the enantiomer. Presumably, the reason for this is that the intensity of the magnetic field of the substrate material is influenced by the chiral molecules after the chiral molecules are loaded, and the different enantiomers have different degrees of influence on the magnetic field intensity, and thus different magnetic field intensity detection results are exhibited when the contents of the enantiomers are different. Furthermore, the influence conforms to a linear rule, so that the content proportion of the enantiomers can be calculated according to the detection result of the magnetic field intensity corresponding to the enantiomers loaded with different proportions, and the chiral compound can be detected.
When the detection method of the embodiment is adopted to detect the chiral compounds, the chiral compounds which are enantiomers can generate magnetic fields with obviously different intensities, and the content proportion can be calculated by measuring the magnetic field intensity through a gauss meter, so that the detection of the chiral compounds is realized. In the detection method of each embodiment, a detection result can be obtained only by loading a sample to be detected on a substrate material and then detecting by adopting a gauss meter while using laser irradiation, and separation of enantiomers is not required, so that compared with the chiral compound detection method in the prior art, the detection method has the advantages of simple operation, accurate result, easy realization of field detection and the like.
The above examples are merely illustrative of specific embodiments of the present invention, and the method for detecting a chiral compound of the present invention is not limited to the scope described in the above examples.
In the embodiment, the material having chiral property is a nano metal film material, a nano metal powder material, a nano metal oxide powder material, etc. having a single chiral structure. However, in the present invention, the material with chiral property may also be other kinds of materials, including micro-nano material powder or micro-nano film material with chiral structure composed of other kinds of organic matter, inorganic matter or organic matter-inorganic matter mixture. Wherein, the inorganic substance can comprise metal and metal oxide, the metal can be one or a combination of more of gold, silver, copper and platinum, and the metal oxide can be one or a combination of more of copper oxide, titanium oxide, zinc oxide, tin oxide, iron oxide and cobalt oxide; the chiral structure may be a plurality of chiral structures such as a propeller structure, in addition to the spiral fiber structure, the flower-shaped structure, and the fan-shaped structure of the embodiment. That is, the substrate material used in the present invention is only required to be a material having chiral photo-magnetic responsiveness, and all of the materials can exhibit different magnetic field strengths under a laser irradiation condition after a sample to be detected carrying a chiral compound, thereby realizing content ratio detection of enantiomers.
Claims (5)
1. A method for detecting chiral compounds is characterized in that a chiral photo-magnetic response material is used as a substrate material to be matched with a gaussmeter so as to detect the chiral compounds, and comprises the following steps:
step S1, placing a sample to be tested of the chiral compound on a substrate material;
step S2, irradiating the sample to be detected with laser, detecting the magnetic field intensity generated after the sample to be detected is irradiated with the laser with a gaussmeter to obtain a detection result,
and the laser irradiating the sample to be detected is unpolarized light.
2. The method for detecting a chiral compound according to claim 1, wherein:
the photo-magnetic responsive material with chirality in step S1 is one or a mixture of several of a metal nano spiral line array, a composite metal nano spiral line array, a metal oxide nano spiral line array and a composite metal oxide nano spiral line array.
3. The method for detecting a chiral compound according to claim 1, further comprising the steps of:
and step S3, analyzing the magnetic field intensity detected in the step S2 to obtain the content of the enantiomer in the chiral compound.
4. The method for detecting a chiral compound according to claim 3, wherein:
wherein the analyzing of step S3 includes the steps of:
step S3-1, preparing a plurality of standard products of the chiral compound, wherein each standard product contains enantiomers of the chiral compound with different amounts;
step S3-2, respectively placing each standard product on the substrate material, respectively irradiating by the laser and detecting the magnetic field intensity generated after the laser irradiates the sample to be detected by the gaussmeter, so as to obtain the magnetic field intensity generated after the irradiation of each standard product;
and S3-3, comparing and analyzing the magnetic field strengths of the standard sample and the sample to be detected to obtain the enantiomer content of the chiral compound in the sample to be detected.
5. The method for detecting a chiral compound according to claim 4, wherein:
wherein the comparative analysis of step S3-3 is: and drawing a standard curve according to the relationship between the magnetic field strength of the standard substance and the enantiomer content, and obtaining the enantiomer content of the chiral compound according to the standard curve and the magnetic field strength of the sample to be detected.
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