CN110031583B - Liquid chromatography method for separating and measuring N-succinyl tryptophan enantiomer - Google Patents
Liquid chromatography method for separating and measuring N-succinyl tryptophan enantiomer Download PDFInfo
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- CN110031583B CN110031583B CN201811629727.0A CN201811629727A CN110031583B CN 110031583 B CN110031583 B CN 110031583B CN 201811629727 A CN201811629727 A CN 201811629727A CN 110031583 B CN110031583 B CN 110031583B
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- UMUNJQFZILKRKP-UHFFFAOYSA-N 2-(2,5-dioxopyrrolidin-1-yl)-3-(1h-indol-3-yl)propanoic acid Chemical class C=1NC2=CC=CC=C2C=1CC(C(=O)O)N1C(=O)CCC1=O UMUNJQFZILKRKP-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000004811 liquid chromatography Methods 0.000 title claims abstract description 8
- 238000001514 detection method Methods 0.000 claims abstract description 14
- 239000007788 liquid Substances 0.000 claims abstract description 9
- XORXDJBDZJBCOC-UHFFFAOYSA-N azanium;acetonitrile;acetate Chemical compound [NH4+].CC#N.CC([O-])=O XORXDJBDZJBCOC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 6
- SIZZGLHHFQZDEC-LBPRGKRZSA-N 4-[[(1s)-1-carboxy-2-(1h-indol-3-yl)ethyl]amino]-4-oxobutanoic acid Chemical class C1=CC=C2C(C[C@H](NC(=O)CCC(=O)O)C(O)=O)=CNC2=C1 SIZZGLHHFQZDEC-LBPRGKRZSA-N 0.000 claims abstract 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 10
- 239000005695 Ammonium acetate Substances 0.000 claims description 9
- 229940043376 ammonium acetate Drugs 0.000 claims description 9
- 235000019257 ammonium acetate Nutrition 0.000 claims description 9
- 239000003085 diluting agent Substances 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 3
- 238000005259 measurement Methods 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims description 2
- 102000008100 Human Serum Albumin Human genes 0.000 claims 1
- 108091006905 Human Serum Albumin Proteins 0.000 claims 1
- 230000014759 maintenance of location Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 abstract description 7
- 239000003814 drug Substances 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 229940079593 drug Drugs 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229960004799 tryptophan Drugs 0.000 description 4
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical class C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- -1 feed science Substances 0.000 description 3
- SIZZGLHHFQZDEC-GFCCVEGCSA-N 4-[[(1r)-1-carboxy-2-(1h-indol-3-yl)ethyl]amino]-4-oxobutanoic acid Chemical compound C1=CC=C2C(C[C@@H](NC(=O)CCC(=O)O)C(O)=O)=CNC2=C1 SIZZGLHHFQZDEC-GFCCVEGCSA-N 0.000 description 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 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 description 1
- 229920002160 Celluloid Polymers 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005251 capillar electrophoresis Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000005220 pharmaceutical analysis Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000003908 quality control method Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/88—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
- G01N2030/8809—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample
- G01N2030/8813—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample biological materials
- G01N2030/8818—Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86 analysis specially adapted for the sample biological materials involving amino acids
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Investigating Or Analysing Biological Materials (AREA)
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Abstract
The invention relates to a liquid chromatography method for separating and measuring N-succinyl tryptophan enantiomer, and the existing detection method has lower efficiency and poorer accuracy. The invention adopts a protein bonding type chiral chromatographic column which mainly comprises the steps of taking ammonium acetate-acetonitrile as a mobile phase and separating and measuring N-succinyl-tryptophan enantiomer. The high performance liquid separation detection method of the N-succinyl tryptophan enantiomer can effectively separate and measure the N-succinyl tryptophan enantiomer, has strong specificity and high accuracy, and can be used for the qualitative and quantitative determination of the N-succinyl tryptophan enantiomer.
Description
Technical Field
The invention belongs to the field of pharmaceutical analysis, and particularly relates to a liquid chromatography method for separating and measuring N-succinyl tryptophan enantiomer.
Background
Amino acids are the basic substances that make up protein macromolecules and are closely related to vital activities. Amino acid analysis plays an important role in the fields of biochemistry, food science, clinical medicine, feed science, chemical industry and the like. The amino acid and the amino acid derivative as a classical chiral compound have inseparable properties such as the determination of the enantiomeric purity, the evaluation of an asymmetric synthesis method, the quality detection of chiral drugs and the like. At present, optical rotation method, NMR method, capillary electrophoresis method, chromatography and the like are widely applied to the determination of the enantiomeric purity, wherein the high performance liquid chromatography which utilizes the chiral chromatographic column for analysis is concerned by people due to the advantages of convenient operation, good reproducibility, small sample dosage and the like, and various commercialized chiral columns with excellent performance are developed.
Tryptophan derivative N-succinyl tryptophan with molecular formula C15H16N2O5The chemical name is N- (3-carboxyl-1-carbonyl-DL-Tryptophan), the foreign name is N- (3-carboxyl-1-oxypyryl) -DL-Tryptophan, and the chemical structural formula is as follows:
the molecule has a chiral center, and two enantiomers of DL exist; as an important intermediate in the process of tryptophan synthesis, the content of N-succinyl tryptophan enantiomer not only affects the final yield, but also the relative content of N-succinyl tryptophan enantiomer affects the optical purity of the product tryptophan, so strict quality control is necessary.
Disclosure of Invention
The invention aims to provide a liquid chromatography method for separating and measuring N-succinyl tryptophan enantiomer.
The purpose of the invention is realized by the following technical scheme:
a high performance liquid phase separation detection method of N-succinyl tryptophan enantiomer adopts a protein bonding type chiral chromatographic column under chromatographic conditions, and ammonium acetate-acetonitrile is used as a flow to separate the N-succinyl tryptophan enantiomer.
The protein-bonded chiral chromatographic column is preferably a CHIRALPAK HAS (150mmX4.0mm) chiral column of Daxylonite drug chiral technology, Inc. (DAICEL CHIRAL TECHNOLOGIES CO. LTD).
The mobile phase is preferably ammonium acetate-acetonitrile, and the volume ratio of the ammonium acetate to the acetonitrile is preferably 85: 15; wherein the organic phase acetonitrile is not replaceable, the concentration of the inorganic salt solution ammonium acetate is 30-50 mM, preferably 50mM, and the pH value is adjusted to 6.5;
in the separation detection method, the following chromatographic conditions are adopted:
the flow rate of the mobile phase is 0.5-0.7 mL/min, preferably 0.6 mL/min;
the chromatographic temperature is 25-30 ℃, and preferably 30 ℃;
the detector adopts an ultraviolet detector, and the detection wavelength is 280 nm.
In a preferred embodiment, the chromatographic conditions of the separation detection method comprise: the chromatographic column is CHIRALPAK HAS (150mmX4.0mM) chiral chromatographic column of Daxylonite medicine chiral technology Co.LTD (DAICEL CHIRAL TECHNOLOGIES CO.LTD), the detector adopts ultraviolet detector (UV), the mobile phase is ammonium acetate-acetonitrile (85:15), wherein the ammonium acetate concentration is 50mM, the pH is adjusted to 6.5, the temperature of the chromatographic column is 30 ℃, the flow rate is 0.6mL/min, and the detection wavelength is 280 nm.
The liquid chromatography method for separating and measuring the N-succinyl tryptophan enantiomer can effectively separate and measure the N-succinyl tryptophan enantiomer, has strong specificity and high accuracy, and can be used for the qualitative and quantitative determination of the N-succinyl tryptophan enantiomer.
Description of the drawings:
FIG. 1 is a high performance liquid chromatogram of N-succinyl tryptophan enantiomer
FIG. 2 is a high performance liquid chromatogram of N-succinyl-L-tryptophan
FIG. 3 is a high performance liquid chromatogram of N-succinyl-D-tryptophan
FIG. 4 is a standard curve of HPLC detection of N-succinyl-L-tryptophan
FIG. 5 is a HPLC detection standard curve for N-succinyl-D-tryptophan.
Detailed Description
The present invention will be further described by the following examples, which, however, are not intended to limit the scope of the present invention in any way. Certain changes and modifications within the scope of the claims, which may be made by one skilled in the art, are also considered to be within the scope of the invention.
Embodiment 1 selection of mobile phase
Apparatus and conditions
The instrument comprises the following steps: shimadzu LC-2030C liquid chromatograph and electronic analytical balance
A chromatographic column: CHIRALPAK HAS (150mmX4.0mm) of Daxylonite drug chiral technology Co.LTD (DAICEL CHIRAL TECHNOLOGIES CO.LTD)
TABLE 1 selection of chromatographic conditions during detection of N-succinyl tryptophan enantiomers
As can be seen from Table 1, when the mobile phase is ammonium acetate-acetonitrile (85:15, V/V) and the concentration of ammonium acetate is 30-50 mM, the main peak pattern in the obtained HPLC chromatogram is good, the separation degree R of the N-succinyl tryptophan enantiomer is greater than 1.5, a good separation effect is achieved, and the standard of Chinese pharmacopoeia is met, so that the condition of the mobile phase for detecting the N-succinyl tryptophan enantiomer is determined by comprehensively considering the ammonium acetate-acetonitrile (85:15, V/V) and the concentration of ammonium acetate is 50 mM.
Example 2 selection of flow Rate and column temperature
Apparatus and conditions
The instrument comprises the following steps: shimadzu LC-2030C liquid chromatograph and electronic analytical balance
A chromatographic column: CHIRALPAK HAS (150mmX4.0mm) of Daxylonite drug chiral technology Co.LTD (DAICEL CHIRAL TECHNOLOGIES CO.LTD)
TABLE 2 selection of chromatographic conditions during detection of N-succinyl tryptophan enantiomers
As can be seen from Table 2, when the flow rate is 0.6mL/min and the column temperature is 30 ℃, the main peak pattern in the obtained HPLC chart is better, the separation degree R of the N-succinyl tryptophan enantiomer is more than 1.5, the good separation effect is achieved, and the standard of Chinese pharmacopoeia is met, so that the chromatographic condition for detecting the N-succinyl tryptophan enantiomer is determined by comprehensively considering that the flow rate is 0.6mL/min and the column temperature is 30 ℃.
EXAMPLE 3 plotting of the enantiomeric detection markers for N-succinyltryptophan
1. Apparatus and conditions
The instrument comprises the following steps: shimadzu LC-2030C liquid chromatograph and electronic analytical balance
A chromatographic column: celluloid pharmaceuticals Manual technology Co., Ltd (DAICEL CHIRAL TECHNOLOGIES CO. LTD) CHIRALPAK HAS (150mmX4.0mm)
Ultraviolet detection wavelength: 280nm
Mobile phase: acetonitrile-ammonium acetate (15:85, V/V) with ammonium acetate concentration of 50mM
Column temperature: 30 deg.C
2. Experimental procedure
Weighing about 0.02g, 0.04g, 0.06g, 0.08g and 0.10g of N-succinyl tryptophan enantiomer into a beaker, ultrasonically dissolving the N-succinyl tryptophan enantiomer with a diluent (15% acetonitrile and 85% 50mM ammonium acetate), transferring the N-succinyl tryptophan enantiomer into a 100mL volumetric flask, and fixing the volume to the scale with the diluent. The instrument automatically samples 10 mul and injects into the liquid chromatograph, records chromatogram.
The measurement results are shown in FIGS. 4 and 5.
As can be seen from FIGS. 4 and 5, the linear range of the standard curve for detecting N-succinyl tryptophan enantiomer obtained from the peak area and the weighed concentration was 0.2-1.0 g/L, and the correlation coefficients R2 of two types of configuration LD of N-succinyl tryptophan were 0.9998 and 0.9999, respectively. The method is simple, convenient and quick, and can be used for separating and detecting the N-succinyl tryptophan enantiomer.
Claims (1)
1. A liquid chromatography method for separating and measuring N-succinyl tryptophan enantiomer is characterized in that: adopting a protein bonding type chiral chromatographic column which mainly comprises taking ammonium acetate-acetonitrile as a mobile phase to separate and measure the N-succinyl-tryptophan enantiomer;
the protein bonded chiral chromatographic column is CHIRALPAKHAS, wherein the bonded protein is human serum albumin;
the concentration of the ammonia acetate is 50 mM;
the volume ratio of the ammonium acetate to the acetonitrile is 85: 15;
in the method, the flow rate of the mobile phase is 0.6ml/min,
the temperature of a chromatographic column in the chromatographic condition is 30 ℃,
the detector adopts an ultraviolet detector, the detection wavelength is 280nm,
the liquid chromatography method for separating and measuring the N-succinyl tryptophan enantiomer comprises the following specific steps:
the method comprises the following steps: solution preparation
Weighing a proper amount of N-succinyl tryptophan enantiomer, placing the N-succinyl tryptophan enantiomer in a beaker, ultrasonically dissolving the N-succinyl tryptophan enantiomer in a diluent of 15% acetonitrile and 85% 50mM ammonium acetate, transferring the mixture into a volumetric flask, fixing the volume to a corresponding scale by using the diluent, and shaking up to obtain the N-succinyl tryptophan enantiomer;
step two: measurement of
An autosampler samples 10 mul and injects the sample into a liquid chromatograph, and the retention time of the chromatogram to the main peak is recorded to be 1.5 times.
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| JP2004057014A (en) * | 2002-07-24 | 2004-02-26 | Univ Waseda | Method for racemizing aromatic amino acid, method for producing optically active substance of aromatic amino acid and microorganism and enzyme having racemizing activity for aromatic amino acid |
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