CN113406183B - Method for efficiently identifying penicillamine chiral enantiomer based on ion mobility mass spectrometer - Google Patents
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- 150000002500 ions Chemical class 0.000 title claims abstract description 48
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 title claims abstract description 27
- 229960001639 penicillamine Drugs 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 20
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims abstract description 45
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 24
- VVNCNSJFMMFHPL-GSVOUGTGSA-N L-penicillamine Chemical compound CC(C)(S)[C@H](N)C(O)=O VVNCNSJFMMFHPL-GSVOUGTGSA-N 0.000 claims abstract description 19
- 238000001228 spectrum Methods 0.000 claims abstract description 12
- 238000004458 analytical method Methods 0.000 claims abstract description 11
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- 229920000858 Cyclodextrin Polymers 0.000 claims description 31
- 239000001116 FEMA 4028 Substances 0.000 claims description 27
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 27
- 229960004853 betadex Drugs 0.000 claims description 27
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 14
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 14
- 229910001416 lithium ion Inorganic materials 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 6
- 238000004949 mass spectrometry Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000005259 measurement Methods 0.000 claims description 2
- 238000001514 detection method Methods 0.000 abstract description 5
- 238000001871 ion mobility spectroscopy Methods 0.000 abstract description 3
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- 238000000926 separation method Methods 0.000 description 6
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
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- 239000012488 sample solution Substances 0.000 description 3
- 101100328463 Mus musculus Cmya5 gene Proteins 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940097362 cyclodextrins Drugs 0.000 description 2
- 238000001212 derivatisation Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
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- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000010413 mother solution Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000000176 thermal ionisation mass spectrometry Methods 0.000 description 2
- 238000013055 trapped ion mobility spectrometry Methods 0.000 description 2
- BTANRVKWQNVYAZ-BYPYZUCNSA-N (2S)-butan-2-ol Chemical compound CC[C@H](C)O BTANRVKWQNVYAZ-BYPYZUCNSA-N 0.000 description 1
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical class NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 1
- TWBPWBPGNQWFSJ-UHFFFAOYSA-N 2-phenylaniline Chemical group NC1=CC=CC=C1C1=CC=CC=C1 TWBPWBPGNQWFSJ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 208000002972 Hepatolenticular Degeneration Diseases 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 208000018839 Wilson disease Diseases 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 238000005251 capillar electrophoresis Methods 0.000 description 1
- -1 carbohydrate enantiomers Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910021397 glassy carbon Inorganic materials 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000000951 ion mobility spectrometry-mass spectrometry Methods 0.000 description 1
- 229960003376 levofloxacin Drugs 0.000 description 1
- 229960001699 ofloxacin Drugs 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 238000004808 supercritical fluid chromatography Methods 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- G01N27/623—Ion mobility spectrometry combined with mass spectrometry
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Electrochemistry (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Abstract
The invention belongs to the technical field of analysis and test, and particularly relates to a method for efficiently identifying penicillamine chiral enantiomers based on an ion mobility mass spectrometer. The invention mixes D-Pen and L-Pen with beta-CD, liCl and so on to prepare mixed solution, and then uses electrospray ionization ion source to produce ternary complex gas phase ions of [ D-pen+beta-CD+Li ] + and [ L-pen+beta-CD+Li ] + ] formed by non-covalent action. Finally, an ion mobility analysis and detection is carried out by using an ion mobility spectrometry device capable of measuring the ion collision section. Because the ion mobility spectrums of the ternary complexes of penicillamine-cyclodextrin-Li + corresponding to different isomers are different, the ion mobility spectrums corresponding to different enantiomers can be obtained, and the analysis and identification of the two enantiomers can be simply, quickly and sensitively realized according to the experimental results of the ion mobility spectrums.
Description
Technical Field
The invention relates to the technical field of analysis and test, in particular to a method for efficiently identifying penicillamine chiral enantiomers based on an ion mobility mass spectrometer.
Background
Chiral is a ubiquitous natural phenomenon, and chiral compounds are found in many organisms, environments, and compound products. Different chiral molecules often perform different functions, for example, the chiral drugs ofloxacin and levofloxacin can cause different pharmaceutical activities, functions, adverse reactions, and the like. The present study of the selectivity and stability of enantiomers has great significance in understanding the effect of individual enantiomers on pharmacological and toxicological activity. Therefore, there is a great deal of interest in how to control the purity of enantiomers in the analytical chemistry and pharmaceutical industry.
Over the past several decades, numerous techniques and methods have been developed to identify and identify chiral compounds, including High Performance Liquid Chromatography (HPLC), capillary electrophoresis, and supercritical fluid chromatography. These methods are mainly based on the fact that by selecting a suitable Chiral Selector (CS), the difference in binding capacity between the enantiomer and the chiral selector allows for an efficient separation. In HPLC, qin et al distinguished chiral tryptophan by beta-cyclodextrin (beta-CD) and acrylamide. Shedania et al replaced methanol with pure acetonitrile and separated 14 chiral sulfides with 12 cellulose chiral columns. Although these methods are widely used, they still have the disadvantages of long time, large sample amount, complex pretreatment of samples, and the like.
Beta-CD molecules are cone-shaped to form a cavity, and are a general chiral selector with 35 stereo centers (FIGS. 1B and C). The 2-and 3-secondary hydroxyl groups are distributed at the openings of the cyclodextrin, and the 6-primary hydroxyl groups are outside the cyclodextrin molecules, so that a structure with relatively hydrophobic inside the cavities and relatively hydrophilic around the openings is formed. Recent studies have also demonstrated good chiral selectivity of cyclodextrins, and the use of binary complexes of cyclodextrins with isomers can achieve efficient separation on IM-MS, such as the aminobiphenyl isomers and the aminobenzenesulfonic acid isomers. Unlike conventional methods, binary complexes bind to enantiomers through non-covalent interactions without reaction and derivatization between enantiomers and CS, the steps for preparing samples are greatly simplified.
In recent years, ion mobility mass spectrometry (IM-MS) has begun to receive increasing attention because of its rapid and efficient performance in enantiomer recognition. When passing through the ion drift tube, gas-phase ions are continuously collided with buffer gas in an electric field, and the difference of collision cross sections is caused due to the difference of the size, the shape and the charge value, so that the gas-phase ions are effectively separated. In 2006, dwivedi et al used (S) -2-butanol as a chiral selector to separate the drug, amino acid and carbohydrate enantiomers, thereby gradually expanding the work of efficient chiral discrimination of enantiomers by combining various CSs based on IM-MS. Shortly thereafter, J.Diana Zhang et al utilized proton-bound diastereomeric dimers based on IM-MS to rapidly differentiate amino acids. Will et al developed a rapid amino acid chiral analysis method based on chiral derivatization of chlornaproxen for IM-MS.
Penicillamine (PENICILLAMINE, pen for short) is an important chiral compound obtained from penicillin for the treatment of wilson's disease, cystiuria and rheumatoid arthritis, with the D-Pen and L-Pen enantiomer structures shown in figure 1A. Wherein D-Pen has a specific pharmacological activity, and L-Pen has a reaction. Wang et al developed a glassy carbon electrode using bovine serum albumin as CS to recognize the Pen enantiomer. However, the use of IM-MS for the analysis and identification of penicillamine (Pen) enantiomers has not been performed.
Disclosure of Invention
Penicillamine (PENICILLAMINE, pen) has two enantiomers, and only D-Pen has been found to be useful in the treatment of cystiuria and rheumatoid arthritis, while L-Pen has a counter-effect. In view of the wide need for analyzing and separating penicillamine and the deficiencies of the currently used separation techniques and methods, the present invention addresses the need for rapid and efficient analytical identification and separation of penicillamine, and provides a method for efficiently identifying chiral enantiomers of penicillamine based on ion mobility mass spectrometry.
The technical scheme for realizing the aim of the invention is as follows: a method for efficiently identifying chiral enantiomers of penicillamine based on ion mobility mass spectrometry, comprising a sample of penicillamine of both D-and L-enantiomers, having a molecular formula of C 5H11NO2 S, comprising the steps of:
S1, adding a solvent to a penicillamine sample, beta-CD and a compound containing lithium ions, which are required to be subjected to enantiomer analysis, to prepare a mixture of pen+beta-CD+lithium ions;
S2, using an ion source to generate monovalent positive ions of the Pen+beta-CD+lithium ions by using the mixture of the pen+beta-CD+lithium ions, namely [ D-pen+beta-CD+Li ] + and [ L-pen+beta-CD+Li ] +, wherein the mass-to-charge ratio is m/z= 1290.43;
S3, measuring ion mobility spectrums of monovalent positive ions of the pen+beta-CD+lithium ions by using an experimental device comprising the ion mobility spectrums, and obtaining a measurement result of the ion mobility spectrums according to a collision section sequence [ L-pen+beta-CD+Li ] +>[D-Pen+β-CD+Li]+, so that structural information of chiral enantiomers of penicillamine molecules can be obtained.
The lithium ion-containing compound in the technical scheme is lithium chloride.
According to the technical scheme, the solvent is a mixed solution of water and methanol.
According to the technical scheme, the content ratio of the penicillamine sample, the beta-CD and the lithium ion-containing compound is any value larger than 0.
The beta-CD is beta-cyclodextrin.
The ion source in the technical scheme is an electrospray ionization ion source.
After the technical scheme is adopted, the invention has the following positive effects:
D-Pen and L-Pen are respectively mixed with beta-CD, liCl and the like to prepare mixed solution, and then an electrospray ionization ion source is used for generating ternary complex gas-phase ions of [ D-pen+beta-CD+Li ] + and [ L-pen+beta-CD+Li ] + ] which are formed through non-covalent actions. Finally, an ion mobility analysis and detection is carried out by using an ion mobility spectrometry device capable of measuring the ion collision section. Because the ion mobility spectrums of the ternary complexes of penicillamine-cyclodextrin-Li + corresponding to different isomers are different, the ion mobility spectrums corresponding to different enantiomers can be obtained, and the analysis and identification of the two enantiomers can be simply, quickly and sensitively realized according to the experimental results of the ion mobility spectrums.
Drawings
In order that the invention may be more readily understood, a more particular description of the invention will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings, in which
FIG. 1 (A) is a schematic diagram of chemical structures of D-Pen and L-Pen;
FIG. 1 (B) is a schematic chemical structure of beta-cyclodextrin;
FIG. 1 (C) is a schematic diagram of the glucose unit structure in beta-cyclodextrin;
FIG. 2 is a mass spectrum detection diagram of a mixed solution of D-Pen and L-Pen, lithium chloride and beta-cyclodextrin;
FIG. 3 shows TIMS separation of D-Pen and L-Pen, lithium chloride, beta-cyclodextrin mixed solution (A) [ D-pen+beta-CD+H ] +;(B)[L-Pen+β-CD+H]+;(C)[D/L-Pen+β-CD+Li]+.
Detailed Description
For the purpose of making the objects, technical solutions and advantages of the embodiments of the present invention more apparent, the technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention, and it is apparent that the described embodiments are some embodiments of the present invention, but not all embodiments of the present invention. The components of the 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.
Example 1
To verify the feasibility and advancement of the method presented in the present invention, the inventors performed ion mobility and mass spectrometry experiments on "penicillamine-cyclodextrin-Li +" ternary complex ions containing chiral penicillamine molecules in positive ion mode using a commercial ion mobility spectrometry-mass spectrometry instrument (TIMS-TOF MS manufactured by Bruke). The primary mass spectrum results are shown in fig. 2, and it can be seen that the ternary complex [ Pen-beta-CD-Li ] + formed by the two isomers, beta-CD and LiCl cannot be separated due to the same mass-to-charge ratio. After TIMS analysis, the ternary complexes of the two isomers were well separated by having different ion mobility, and the results are shown in FIG. 3.
(1) Preparation of sample solutions
Firstly, weighing a certain amount of D-Pen and L-Pen standard substances, beta-cyclodextrin and LiCl solid on an analytical balance, and dissolving the D-Pen and L-Pen standard substances, beta-cyclodextrin and LiCl solid on a proper solvent to prepare a mother solution with the concentration of 10 -2 M. Respectively taking 10uL of mother solution, diluting to 1mL by taking methanol/water/formic acid (1:1:0.001, v/v/v) as a solvent to obtain 10 -4 M of mixed sample solution of D-Pen+beta-CD+Li + and L-pen+beta-CD+Li +, and shaking uniformly for later use.
(2) Sample detection
First, TIMS-TOF calibration is carried out, and a sample solution is detected by adopting manual sample injection. Instrument parameters: an electrospray ion source; a positive ion mode; sample injection flow rate: 3 mu L/min; electrospray voltage: 3600V; atomizing gas: 0.3bar; drying gas flow rate: 3.0L/min; drying gas temperature: 200 ℃; ramp time 500ms. And analyzing the detection result.
While the foregoing is directed to embodiments of the present invention, other and further details of the invention may be had by the present invention, it should be understood that the foregoing description is merely illustrative of the present invention and that no limitations are intended to the scope of the invention, except insofar as modifications, equivalents, improvements or modifications are within the spirit and principles of the invention.
Claims (5)
1. A method for efficiently identifying chiral enantiomers of penicillamine based on ion mobility mass spectrometry, comprising a sample of penicillamine having the formula C5H 11 NO 2S, and two enantiomers, D-and L-, comprising the steps of: s1, adding a solvent into a penicillamine sample, beta-CD and a lithium ion-containing compound to be subjected to enantiomer analysis to prepare a mixture of pen+beta-CD+lithium ions, wherein the content ratio of the penicillamine sample to the beta-CD to the lithium ion-containing compound is any value larger than 0;
S2, using an ion source to generate monovalent positive ions of the Pen+beta-CD+lithium ions by using the mixture of the pen+beta-CD+lithium ions, namely [ D-pen+beta-CD+Li ] + and [ L-pen+beta-CD+Li ] +, wherein the mass-to-charge ratio is m/z= 1290.43;
S3, measuring ion mobility spectrums of monovalent positive ions of the pen+beta-CD+lithium ions by using an experimental device comprising the ion mobility spectrums, and obtaining a measurement result of the ion mobility spectrums according to a collision section sequence [ L-pen+beta-CD+Li ] +>[D-Pen+β-CD+Li]+, so that structural information of chiral enantiomers of penicillamine molecules can be obtained.
2. The method for efficiently identifying penicillamine chiral enantiomers based on an ion mobility mass spectrometer of claim 1, wherein the method comprises the steps of: the lithium ion-containing compound is lithium chloride.
3. The method for efficiently identifying penicillamine chiral enantiomers based on an ion mobility mass spectrometer of claim 1, wherein the method comprises the steps of: the solvent is a mixed solution of water and methanol.
4. The method for efficiently identifying penicillamine chiral enantiomers based on an ion mobility mass spectrometer of claim 1, wherein the method comprises the steps of: the beta-CD is beta-cyclodextrin.
5. The method for efficiently identifying penicillamine chiral enantiomers based on an ion mobility mass spectrometer of claim 1, wherein the method comprises the steps of: the ion source is an electrospray ionization ion source.
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| JPH083131A (en) * | 1990-03-27 | 1996-01-09 | Sumika Bunseki Center:Kk | Penicillamine derivative, chirality discriminating agent and separating agent |
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| CN103880721A (en) * | 2014-03-05 | 2014-06-25 | 上海师范大学 | Method of separating chiral drug penicillamine enantiomer based on functional gold nanochannel |
| CN108414664A (en) * | 2018-04-11 | 2018-08-17 | 国家烟草质量监督检验中心 | A kind of method that ultra high efficiency conjunction phase chromatography-tandem mass spectrum technology splits, measures Chiral pesticide isopropyl methoxalamine enantiomer |
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