CN112824888B - Analytical reagent and method for aminobenzenesulfonic acid positional isomer based on beta cyclodextrin - Google Patents
Analytical reagent and method for aminobenzenesulfonic acid positional isomer based on beta cyclodextrin Download PDFInfo
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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
- G01N27/62—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating the ionisation of gases, e.g. aerosols; by investigating electric discharges, e.g. emission of cathode
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- G—PHYSICS
- G01—MEASURING; TESTING
- 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
- G01N27/62—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating the ionisation of gases, e.g. aerosols; by investigating electric discharges, e.g. emission of cathode
- G01N27/622—Ion mobility spectrometry
Abstract
The invention relates to an analytical reagent of aminobenzenesulfonic acid positional isomer based on beta cyclodextrin, which comprises aminobenzenesulfonic acid isomer molecules mixed with a solvent, beta cyclodextrin and a compound containing univalent lithium ions. The structural analysis method of the aminobenzenesulfonic acid isomers at different positions is simple, the aminobenzenesulfonic acid molecules do not need to be subjected to pre-resolution or derivatization, and the used chemical samples are easy to obtain, low in price, non-toxic and harmless, and have a plurality of advantages compared with the conventional method.
Description
Technical Field
The invention relates to the technical field of analysis and test, in particular to an analysis reagent and an analysis method of aminobenzene sulfonic acid position isomer based on beta cyclodextrin.
Background
Molecules are the most basic building blocks of the physical world, while positional isomers are one of the basic properties of molecules. These compounds are called positional isomers, with the same composition and different positions on the carbon skeleton (carbon chain or carbon ring) of substituents or functional groups (including carbon-carbon double and triple bonds) in the molecule. The positional isomer is an isomerization phenomenon in which positional isomers occur due to a difference in position of a substituent or a functional group on a carbon chain or a carbon ring, and belongs to one of isomers.
Positional isomers are central concepts in organic chemistry and may have a significant impact on the properties of the molecule. Many disubstituted benzene compounds are environmental pollutants, drug metabolites or intermediates in the chemical and pharmaceutical industries. In addition, positional isomerism often has different chemical and pharmaceutical properties. For example, the three-position isomerism of 2-aminobenzenesulfonic acid (2-ABSA), 3-ABSA and 4-ABSA, where 4-ABSA is an important compound for the synthesis and characterization of sulfamethoxazole and sulfanilamide proteins and lysine conjugates. Acids used to study sulfonamide allergies, while 2-ABSA and 3-ABSA are reactive dye intermediates, while 3-ABSA is highly toxic. In this case, the separation of the three positional isomers is of crucial importance. However, isomers generally have similar physical and chemical properties, and their separation is therefore one of the most challenging areas in the science of separation.
At present, the separation and detection of aminobenzenesulfonic acid ester substances are mainly High Performance Liquid Chromatography (HPLC), and a C18 column is often used for separation, because aminobenzenesulfonic acid substances have strong polarity, phosphate buffer solution is mostly used as a mobile phase, and the retention time is short, so that aminobenzenesulfonic acid substances are difficult to separate from impurities, and even accurate quantification of aminobenzenesulfonic acid substances is interfered. Therefore, it is very important to develop a simple and fast method for separating and detecting the content of the positional isomer of the aminobenzene sulfonic acid substances, and the method is also one of the key problems in the research of the positional isomer at present.
The mass spectrometry is the most commonly used molecular or atomic mass analysis technology, which can rapidly analyze the mass-to-charge ratio or mass information of different atoms or molecules, but has no effect on chiral molecules with the same mass-to-charge ratio and molecular mass. The ion mobility spectrometry technology can analyze molecules with different structures like a fractal body, and the working principle and the process of the ion mobility spectrometry technology are that ions of a sample to be analyzed are firstly generated and then are introduced into the ion mobility spectrometry, and the general ion mobility spectrometry works under the low vacuum condition. In ion mobility spectrometry, sample ions make directional motion under the action of an electric field and continuously collide with nonreactive working gases in the mobility spectrometry, such as nitrogen, argon and the like. Different ions are separated by their different mobilities due to their different collision cross sections. Information on the structure of the ion or molecule can be obtained from the separated ion mobility spectrum obtained. However, because the resolution capability of the current ion mobility spectrometry is low, the structure difference of the molecules is small, or the molecules are very small, such as organic small molecules, small molecule drugs and the like, the ion mobility spectrometry technology still cannot analyze the structure difference, particularly the structure difference of different position isomers, such as the position structure analysis of aminobenzenesulfonic acid substances.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides an analytical reagent and a method for aminobenzenesulfonic acid positional isomer based on beta cyclodextrin.
The technical scheme for realizing the purpose of the invention is as follows: an analytical reagent for aminobenzenesulfonic acid positional isomers based on beta cyclodextrin, comprising aminobenzenesulfonic acid isomer molecules mixed with a solvent, beta cyclodextrin and a compound containing monovalent lithium ions.
The concentration of the aminobenzenesulfonic acid isomer molecule in the technical scheme is 10-121 mol/L, the concentration of the beta cyclodextrin is 10-12About 1 mol/l, containingThe concentration of the compound having monovalent lithium ion was 10-12-1 mole/liter, the relative proportions between said aminobenzenesulfonic acid isomer molecules, said beta-cyclodextrin and said compound containing monovalent lithium ions being not limited.
The aminobenzenesulfonic acid isomer molecule in the technical scheme has three types of 2-aminobenzenesulfonic acid, 3-aminobenzenesulfonic acid and 4-aminobenzenesulfonic acid.
The compound containing monovalent lithium ions in the technical scheme is one of lithium halide (except F), lithium nitrate, lithium chlorate, lithium perchlorate, lithium bicarbonate, lithium dihydrogen phosphate, lithium gluconate, lithium hydrogen phosphate, lithium lactate, alkali containing lithium ions and a complex containing lithium ions.
The beta cyclodextrin in the technical scheme comprises a derivative of the beta cyclodextrin.
In the technical scheme, the solvent is one or more of deionized water, methanol, ethanol, ether, acetic acid, acetonitrile and formic acid water.
An analytical method of aminobenzenesulfonic acid positional isomer based on beta cyclodextrin comprises the following steps:
s1, adding a solvent into aminobenzenesulfonic acid isomer molecules, beta cyclodextrin and a compound containing monovalent lithium ions to be subjected to isomer analysis to prepare an aminobenzenesulfonic acid-beta cyclodextrin-lithium ion-containing mixture;
s2, the mixture of aminobenzenesulfonic acid-beta-cyclodextrin-lithium-containing ions uses an ion source to generate univalent positive ions of aminobenzenesulfonic acid-beta-cyclodextrin-lithium-containing ions, namely [ C6H7NO3S-βCD-Li]+Mass to charge ratio of m/z = 1314.4;
s3, measuring the ion collision cross section of the monovalent positive ions of the aminobenzenesulfonic acid-beta cyclodextrin-lithium-containing ions, or measuring the ion mobility spectrum of the monovalent positive ions of the aminobenzenesulfonic acid-beta cyclodextrin-lithium-containing ions by using an experimental device comprising an ion mobility spectrum, so as to obtain the position isomeric structure information of aminobenzenesulfonic acid molecules.
In the above technical solution S1, the ion source is one of an electrospray ionization ion source ESI, a laser-assisted desorption ionization ion source MALDI, and a desorption electrospray ionization ion source DESI.
The experimental device in the technical scheme is one of an ion mobility spectrometry and a composite experimental device comprising the ion mobility spectrometry.
After the technical scheme is adopted, the invention has the following positive effects:
the invention provides an analytical reagent and method for aminobenzenesulfonic acid positional isomer based on beta-cyclodextrin, which is prepared by simply mixing aminobenzenesulfonic acid sample with beta-cyclodextrin and containing Li ions (Li ions)+) The compound of (1), such as LiCl, etc., is prepared into a mixed solution, and then is ionized by electric spray to generate' aminobenzenesulfonic acid-beta cyclodextrin-lithium ion-containing monovalent positive ion, namely [ C6H7NO3S-βCD-Li]+And then measuring the ion mobility spectrometry by using the ion mobility spectrometry technology to obtain the structure information of different positions of the aminobenzenesulfonic acid molecule. Furthermore, if the samples contain aminobenzenesulfonic acid molecules with different positional isomers, the method provided by the invention can also obtain the information of the relative content of the aminobenzenesulfonic acid molecules.
The structural analysis method of the aminobenzenesulfonic acid isomers at different positions is simple, the aminobenzenesulfonic acid molecules do not need to be subjected to pre-resolution or derivatization, and the used chemical samples are easy to obtain, low in price, non-toxic and harmless. Compared with the method commonly used at present, the method has many advantages.
Drawings
In order that the present disclosure may be more readily and clearly understood, reference is now made to the following detailed description of the present disclosure taken in conjunction with the accompanying drawings, in which
FIG. 1, a schematic diagram of the chemical structure of three positional isomers of aminobenzenesulfonic acid;
FIG. 2 is a schematic diagram of the chemical structure of beta-cyclodextrin;
FIG. 3 is a mass spectrometric image of a mixture of three aminobenzenesulfonic acids, lithium chloride and beta-cyclodextrin;
FIG. 4 shows TIMS separation of three positional isomers of aminobenzenesulfonic acid, lithium chloride and beta-cyclodextrin mixture (a) [ 2-ABSA-beta CD-Li ]]+；(b) [3-ABSA-βCD-Li]+；(c) [4-ABSA-βCD-Li]+；(d) [ABSAMixing of-βCD-Li]+。
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are some, but not all, embodiments of the present invention. The components of embodiments of the present invention generally described and illustrated in the figures herein may be arranged and designed in a wide variety of different configurations.
The inventor analyzes the structure of the position isomer of aminobenzenesulfonic acid molecule by using a commercial ion mobility spectrometry-mass spectrometry combined instrument-TIMS-TOFMS instrument manufactured by Bruke company, and the primary mass spectrum result is shown in figure 3, and can see that the compound [ C ] formed by aminobenzenesulfonic acid substances of three different position isomers, beta cyclodextrin and metal salt LiCl6H7NO3S-βCD-Li]+ No separation was obtained. After passage through TIMS, the three regioisomeric species were well separated (FIG. 4). It is clear from the experimental results that three aminobenzenesulfonic acid molecules having different positional isomers can be easily distinguished.
Taking three position isomeric aminobenzenesulfonic acid standards, beta-cyclodextrin and LiCl, and mixing the three position isomeric aminobenzenesulfonic acid standards with a ratio of 1: 1: 1 is proportioned to a concentration of 10-4The solvent of the mixed solution is 50 percent of methanol and 50 percent of formic acid water, and the formic acid water solution is 0.1 percent of formic acid water solution. Directly carrying out detection analysis on the prepared solution by TIMS-TOF, wherein the ion source voltage is 2.5-4.5 kV, and the sample injection flow rate is 1-5 mu L/min; the atomizer pressure was 0.3 bar; the drying gas is 3L/min at 200 ℃, and the detection result is analyzed, and the analysis result is shown in figures 3 and 4.
The above-mentioned embodiments are intended to illustrate the objects, technical solutions and advantages of the present invention in further detail, and it should be understood that the above-mentioned embodiments are only exemplary embodiments of the present invention, and are not intended to limit the present invention, and any modifications, equivalents, improvements and the like made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (8)
1. An analytical method of aminobenzenesulfonic acid positional isomer based on beta cyclodextrin is characterized in that: the analytical reagent comprises aminobenzenesulfonic acid isomer molecules mixed with a solvent, beta cyclodextrin and a compound containing univalent lithium ions;
the use of the assay reagent has the following steps:
s1, adding a solvent into aminobenzenesulfonic acid isomer molecules, beta cyclodextrin and a compound containing monovalent lithium ions to be subjected to isomer analysis to prepare an aminobenzenesulfonic acid-beta cyclodextrin-lithium ion-containing mixture;
s2, the mixture of aminobenzenesulfonic acid-beta-cyclodextrin-lithium-containing ions uses an ion source to generate univalent positive ions of aminobenzenesulfonic acid-beta-cyclodextrin-lithium-containing ions, namely [ C6H7NO3S-βCD-Li]+Mass to charge ratio of m/z = 1314.4;
s3, measuring the ion collision cross section of the monovalent positive ions of the aminobenzenesulfonic acid-beta cyclodextrin-lithium-containing ions, or measuring the ion mobility spectrum of the monovalent positive ions of the aminobenzenesulfonic acid-beta cyclodextrin-lithium-containing ions by using an experimental device comprising an ion mobility spectrum, so as to obtain the position isomeric structure information of aminobenzenesulfonic acid molecules.
2. The method for analyzing aminobenzenesulfonic acid positional isomer based on beta-cyclodextrin as claimed in claim 1, wherein: the concentration of aminobenzenesulfonic acid isomer molecules is 10-12About 1 mol/l, the concentration of the beta cyclodextrin is 10-12About 1 mol/l, concentration of the compound containing monovalent lithium ion is 10-12-1 mole/liter, the relative proportions between said aminobenzenesulfonic acid isomer molecules, said beta-cyclodextrin and said compound containing monovalent lithium ions being not limited.
3. The method for analyzing aminobenzenesulfonic acid positional isomer based on beta-cyclodextrin as claimed in claim 1, wherein: the aminobenzenesulfonic acid isomer molecules comprise three types of 2-aminobenzenesulfonic acid, 3-aminobenzenesulfonic acid and 4-aminobenzenesulfonic acid.
4. The method for analyzing aminobenzenesulfonic acid positional isomer based on beta-cyclodextrin as claimed in claim 1, wherein: the compound containing monovalent lithium ions is one of lithium halide, lithium nitrate, lithium chlorate, lithium perchlorate, lithium bicarbonate, lithium dihydrogen phosphate, lithium gluconate, lithium hydrogen phosphate, lithium lactate, lithium ion-containing alkali and lithium ion-containing complex except for F.
5. The method for analyzing aminobenzenesulfonic acid positional isomer based on beta-cyclodextrin as claimed in claim 1, wherein: the beta cyclodextrin includes derivatives of beta cyclodextrin.
6. The method for analyzing aminobenzenesulfonic acid positional isomer based on beta-cyclodextrin as claimed in claim 1, wherein: the solvent is one or more of deionized water, methanol, ethanol, diethyl ether, acetic acid acetonitrile and formic acid water.
7. The method for analyzing aminobenzenesulfonic acid positional isomer based on beta-cyclodextrin as claimed in claim 1, wherein: in S1, the ion source is one of an electrospray ionization ion source ESI, a laser assisted desorption ionization ion source MALDI, and a desorption electrospray ionization ion source DESI.
8. The method for analyzing aminobenzenesulfonic acid positional isomer based on beta-cyclodextrin as claimed in claim 1, wherein: the experimental device is one of an ion mobility spectrometry and a composite experimental device comprising the ion mobility spectrometry.
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| CN202010703683.2A CN112824888B (en) | 2020-07-21 | 2020-07-21 | Analytical reagent and method for aminobenzenesulfonic acid positional isomer based on beta cyclodextrin |
| PCT/CN2021/119185 WO2022017547A1 (en) | 2020-07-21 | 2021-09-17 | Beta cyclodextrin-based, aminobenzene sulfonic acid positional isomer analysis reagent and method |
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