CN106383185B - The high-efficiency liquid chromatography method for detecting of carbobenzyloxy-L-alanine - Google Patents
The high-efficiency liquid chromatography method for detecting of carbobenzyloxy-L-alanine Download PDFInfo
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- CN106383185B CN106383185B CN201610774833.2A CN201610774833A CN106383185B CN 106383185 B CN106383185 B CN 106383185B CN 201610774833 A CN201610774833 A CN 201610774833A CN 106383185 B CN106383185 B CN 106383185B
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- carbobenzyloxy
- alanine
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- liquid chromatography
- mobile phase
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- TYRGLVWXHJRKMT-QMMMGPOBSA-N n-benzyloxycarbonyl-l-serine-betalactone Chemical compound OC(=O)[C@H](C)NC(=O)OCC1=CC=CC=C1 TYRGLVWXHJRKMT-QMMMGPOBSA-N 0.000 title claims abstract description 33
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000004811 liquid chromatography Methods 0.000 title claims abstract description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000012071 phase Substances 0.000 claims abstract description 21
- 238000001514 detection method Methods 0.000 claims abstract description 14
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims abstract description 10
- 235000019796 monopotassium phosphate Nutrition 0.000 claims abstract description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007791 liquid phase Substances 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 8
- 239000000741 silica gel Substances 0.000 claims abstract description 8
- 229960001866 silicon dioxide Drugs 0.000 claims abstract description 8
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 19
- 239000013558 reference substance Substances 0.000 claims description 17
- 238000012360 testing method Methods 0.000 claims description 16
- 239000012488 sample solution Substances 0.000 claims description 15
- 239000000523 sample Substances 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 9
- 238000001914 filtration Methods 0.000 claims description 6
- 238000010812 external standard method Methods 0.000 claims description 4
- 238000005070 sampling Methods 0.000 claims description 4
- 238000007872 degassing Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 3
- 235000016236 parenteral nutrition Nutrition 0.000 description 3
- HJCMDXDYPOUFDY-WHFBIAKZSA-N Ala-Gln Chemical compound C[C@H](N)C(=O)N[C@H](C(O)=O)CCC(N)=O HJCMDXDYPOUFDY-WHFBIAKZSA-N 0.000 description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
- 229960003767 alanine Drugs 0.000 description 2
- 235000004279 alanine Nutrition 0.000 description 2
- 108010044940 alanylglutamine Proteins 0.000 description 2
- 229960002648 alanylglutamine Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 108010016626 Dipeptides Proteins 0.000 description 1
- 206010020674 Hypermetabolism Diseases 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000012372 quality testing Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000009469 supplementation Effects 0.000 description 1
Classifications
-
- 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
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- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of high-efficiency liquid chromatography method for detecting of carbobenzyloxy-L-alanine, chromatographic conditions are as follows: chromatographic column: amino bonded silicagel column；Mobile phase: 0.05mol/L potassium dihydrogen phosphate aqueous solution is 35:65-75 with acetonitrile volume ratio；Wherein, 0.05mol/L potassium dihydrogen phosphate aqueous solution pH value is 4.0；Flow rate of mobile phase: 0.7-1ml/min；Detection wavelength: 215nm；Chromatographic column column temperature: 30 DEG C；Efficient liquid phase chromatographic analysis is carried out, the content of carbobenzyloxy-L-alanine is measured.The method of the present invention can be quick, and Accurate Determining goes out the content of carbobenzyloxy-L-alanine, it is ensured that its is quality controllable, reduces error, save the cost is easy to operate, and detection time is short, improves production efficiency.
Description
Technical field
The present invention relates to column chromatographies to measure compounds content technical field.
Background technique
Glutamine dipeptide (alanyl glutamine) is parenteral nutrition, and can be infused supplement glutamine via parenteral nutrition, point
The amino acid that solution releases respectively is stored in the corresponding site of body as nutriment and be metabolized with body.It is suitable
For requiring supplementation with the parenteral nutrition of glutamine patient, the patient including being in catabolism and hypermetabolism situation.
Carbobenzyloxy-L-alanine (CBZ-L- alanine) is the starting material for preparing alanyl glutamine, due to life
It is antenatal to carry out quality testing to bulk pharmaceutical chemicals.It is disclosed in the prior art using C18Chromatographic column, 0.01% phosphoric acid: the flowing of acetonitrile
Phase, but this method detection time is long, and a sample needs 65min, and needs gradient elution, to high performance liquid chromatograph, prepares and flows
The reagent requirement of phase is higher.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of high performance liquid chromatography detection sides of carbobenzyloxy-L-alanine
Method, this method can be quick, and Accurate Determining goes out the content of carbobenzyloxy-L-alanine, it is ensured that its is quality controllable, reduces error, section
About cost, easy to operate, detection time is short, improves production efficiency.
In order to solve the above technical problems, the technical solution used in the present invention is: a kind of height of carbobenzyloxy-L-alanine
Effect liquid phase chromatogram detection method, chromatographic condition are as follows:
Chromatographic column: amino bonded silicagel column；
Mobile phase: 0.05mol/L potassium dihydrogen phosphate aqueous solution is 35:65-75 with acetonitrile volume ratio；Wherein, 0.05mol/L
Potassium dihydrogen phosphate aqueous solution pH value is 4.0；
Flow rate of mobile phase: 0.7-1ml/min；
Detection wavelength: 215nm；
Chromatographic column column temperature: 30 DEG C；
Efficient liquid phase chromatographic analysis is carried out, the content of carbobenzyloxy-L-alanine is measured.
Preferably, the high-efficiency liquid chromatography method for detecting of carbobenzyloxy-L-alanine, comprising the following steps:
(1) mobile phase is prepared, pH value, filtering, degassing are adjusted；
(2) high performance liquid chromatograph condition, booting balance chromatographic column are adjusted；
(3) preparation of reference substance solution and testing sample solution: precision weigh carbobenzyloxy-L-alanine reference substance and to
Sample, respectively with flowing phased soln constant volume to get；
(4) high performance liquid chromatograph will be injected after reference substance solution, testing sample solution filtering, records chromatogram and peak face
Product calculates the content of carbobenzyloxy-L-alanine in sample to be tested using external standard method.
Preferably, mobile phase are as follows: 0.05mol/L potassium dihydrogen phosphate aqueous solution is 35:75 with acetonitrile volume ratio.
Preferably, flow rate of mobile phase are as follows: 0.7ml/min.
Preferably, chromatogram column length 250mm, internal diameter 4.6mm, packing material size are 5 μm.
Preferably, in step (3), the concentration of reference substance solution and testing sample solution is 0.20-0.21mg/ml.
It is further preferred that the sampling volume of reference substance solution and testing sample solution is 20 μ l in step (4).
The beneficial effects of adopting the technical scheme are that the present invention uses amino bonded silicagel column, carry out high
Effect liquid phase chromatogram analysis, can go out the content of carbobenzyloxy-L-alanine, by this method Accurate Determining to prepare alanine paddy
Glutamine provides initial data, it is ensured that its is quality controllable, reduces error, save the cost is easy to operate, and its appearance time 4-
8min, detection time is short, improves work efficiency.It is not only suitable for the inspection of carbobenzyloxy-L-alanine content in large-scale production
It surveys, is also applied for the detection and analysis in laboratory.
Detailed description of the invention
The present invention will be further described in detail below with reference to the accompanying drawings and specific embodiments；
Fig. 1 is the high-efficient liquid phase chromatogram of reference substance solution in the embodiment of the present invention 1；
Fig. 2 is the high-efficient liquid phase chromatogram of testing sample solution in the embodiment of the present invention 1.
Specific embodiment
The embodiment of the present invention is only used to illustrate realization technical solution of the present invention, these embodiments are not to the present invention
Composition further limits, and in following embodiment, uses high performance liquid chromatograph for Japanese Shimadzu LC-15C, SPD-15C, chromatographic column
For amino bonded silicagel column, GRACE, 250mm*4.6mm, 5 μm, sampling volume is 20 μ l(quantitative loops), other factories can also be used
The high performance liquid chromatograph of family and model, amino bonded silicagel column and other sampling volumes, are attained by the purpose of the present invention.
Embodiment 1-3
Chromatographic condition:
Chromatographic column: amino bonded silicagel column, GRACE, 250mm*4.6mm, 5 μm；
Mobile phase: 0.05mol/l potassium dihydrogen phosphate aqueous solution (phosphoric acid tune pH to 4.0) is 35:75 with acetonitrile volume ratio；
Flow rate of mobile phase: 0.7ml/min；
Detection wavelength: 215nm；
Chromatographic column temperature: 30 DEG C；
Experimental procedure:
(1) mobile phase is prepared, pH value, filtering, degassing are adjusted；
(2) high performance liquid chromatograph condition, booting balance chromatographic column are adjusted；
(3) preparation of reference substance solution and testing sample solution:
Reference substance solution: carbobenzyloxy-L-alanine reference substance 10.0mg is weighed in 50ml volumetric flask, is mixed with flowing
Solve and be diluted to scale, shake up to get；
Testing sample solution: carbobenzyloxy-L-alanine sample to be tested 10.0mg is weighed in 50ml volumetric flask, with flowing
Phased soln is simultaneously diluted to scale, shake up to get；
(4) high performance liquid chromatograph will be injected after reference substance solution, testing sample solution filtering, records chromatogram and peak face
Product calculates the content of carbobenzyloxy-L-alanine in sample to be tested using external standard method；
External standard method calculates the content formula of carbobenzyloxy-L-alanine in sample to be tested are as follows:
X(%)=CIt is right×ASample/AIt is right/CSample*100
CIt is rightFor the concentration of carbobenzyloxy-L-alanine in reference substance solution, unit mg/ml；
AIt is rightFor the peak area or peak height of reference substance solution chromatogram；
ASampleFor the peak area or peak height of testing sample solution chromatogram；
CSampleFor the concentration of solution to be measured in testing sample solution, unit mg/ml；
(5) 1 testing sample solution chromatogram of embodiment, as shown in Figure 2,5.218min are carbobenzyloxy-L-alanine
Peak, remaining is miscellaneous peak, and main peak appearance time is suitable for that theoretical cam curve is greater than 5000 and good with impurity peaks separating degree.
Embodiment 4
The difference from embodiment 1 is that chromatographic condition:
Mobile phase: 0.05mol/l potassium dihydrogen phosphate aqueous solution (phosphoric acid tune pH to 4.0) is 35:65 with acetonitrile volume ratio；
Flow rate of mobile phase: 1ml/min.
Embodiment 5
The difference from embodiment 1 is that chromatographic condition:
Mobile phase: 0.05mol/l potassium dihydrogen phosphate aqueous solution (phosphoric acid tune pH to 4.0) is 35:70 with acetonitrile volume ratio；
Flow rate of mobile phase: 0.8ml/min.
Specific value as shown in the table below:
The present invention uses amino bonded silicagel column, carries out efficient liquid phase chromatographic analysis, can pass through this method Accurate Determining
The content of carbobenzyloxy-L-alanine out provides initial data to prepare alanine glutamine, it is ensured that its is quality controllable, subtracts
Small error, save the cost is easy to operate, and its appearance time 4-8min, and detection time is short, improves work efficiency.Both it was applicable in
The detection of carbobenzyloxy-L-alanine content in large-scale production, is also applied for the detection and analysis in laboratory.
Claims (6)
1. a kind of high-efficiency liquid chromatography method for detecting of carbobenzyloxy-L-alanine, which is characterized in that its chromatographic condition are as follows:
Chromatographic column: amino bonded silicagel column, GRACE, 250mm*4.6mm, 5 μm；
Mobile phase: 0.05mol/L potassium dihydrogen phosphate aqueous solution is 35:65-75 with acetonitrile volume ratio；Wherein, 0.05mol/L phosphoric acid
Potassium dihydrogen pH value of water solution is 4.0；
Flow rate of mobile phase: 0.7-1ml/min；
Detection wavelength: 215nm；
Chromatographic column column temperature: 30 DEG C；
Efficient liquid phase chromatographic analysis is carried out, the content of carbobenzyloxy-L-alanine is measured.
2. the high-efficiency liquid chromatography method for detecting of carbobenzyloxy-L-alanine according to claim 1, which is characterized in that
The following steps are included:
(1) mobile phase is prepared, pH value, filtering, degassing are adjusted；
(2) high performance liquid chromatograph condition, booting balance chromatographic column are adjusted；
(3) preparation of reference substance solution and testing sample solution: precision weighs carbobenzyloxy-L-alanine reference substance and to test sample
Product, respectively with flowing phased soln constant volume to get；
(4) high performance liquid chromatograph will be injected after reference substance solution, testing sample solution filtering, records chromatogram and peak area,
The content of carbobenzyloxy-L-alanine in sample to be tested is calculated using external standard method.
3. the high-efficiency liquid chromatography method for detecting of carbobenzyloxy-L-alanine according to claim 1, it is characterised in that institute
State mobile phase are as follows: 0.05mol/L potassium dihydrogen phosphate aqueous solution is 35:75 with acetonitrile volume ratio.
4. the high-efficiency liquid chromatography method for detecting of carbobenzyloxy-L-alanine according to claim 1, it is characterised in that institute
State flow rate of mobile phase are as follows: 0.7ml/min.
5. the high-efficiency liquid chromatography method for detecting of carbobenzyloxy-L-alanine according to claim 2, it is characterised in that:
In step (3), the concentration of reference substance solution and testing sample solution is 0.20-0.21mg/ml.
6. the high-efficiency liquid chromatography method for detecting of carbobenzyloxy-L-alanine according to claim 5, it is characterised in that:
In step (4), the sampling volume of reference substance solution and testing sample solution is 20 μ l.
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| CN108037206A (en) * | 2017-12-20 | 2018-05-15 | 精晶药业股份有限公司 | A kind of efficient liquid phase detection method of Beta-alanine |
| CN109725099A (en) * | 2019-03-05 | 2019-05-07 | 内蒙古精晶生物科技有限公司 | A kind of efficient liquid phase detection method of valine |
| CN112557574B (en) * | 2020-12-31 | 2023-05-09 | 成都普康生物科技有限公司 | Method for measuring content of CBZ-AEEA |
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|---|---|---|---|---|
| CN105510497A (en) * | 2015-11-30 | 2016-04-20 | 精晶药业股份有限公司 | Quantitative detection method of L-alanyl-L-alanine |
| CN105675756A (en) * | 2016-01-25 | 2016-06-15 | 江南大学 | HPLC (high performance liquid chromatography) detection method for simultaneously determining five substances in reaction system for producing L-Ala-L-Gln (L-alanyl-L-glutamine) with microbial enzyme method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105510497A (en) * | 2015-11-30 | 2016-04-20 | 精晶药业股份有限公司 | Quantitative detection method of L-alanyl-L-alanine |
| CN105675756A (en) * | 2016-01-25 | 2016-06-15 | 江南大学 | HPLC (high performance liquid chromatography) detection method for simultaneously determining five substances in reaction system for producing L-Ala-L-Gln (L-alanyl-L-glutamine) with microbial enzyme method |
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Denomination of invention: Determination of Benzyloxycarbonyl-L-alanine by High Performance Liquid Chromatography Effective date of registration: 20221010 Granted publication date: 20190917 Pledgee: Ningjin Sub branch of Xingtai Bank Co.,Ltd. Pledgor: JING JING PHARMACEUTICAL Co.,Ltd. Registration number: Y2022130000091 |
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Denomination of invention: High performance liquid chromatography detection method for benzyloxycarbonyl-L-alanine Effective date of registration: 20230922 Granted publication date: 20190917 Pledgee: Ningjin Sub branch of Xingtai Bank Co.,Ltd. Pledgor: JING JING PHARMACEUTICAL Co.,Ltd. Registration number: Y2023980058579 |
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Denomination of invention: High performance liquid chromatography detection method for benzyloxycarbonyl-L-alanine Granted publication date: 20190917 Pledgee: Ningjin Sub branch of Xingtai Bank Co.,Ltd. Pledgor: JING JING PHARMACEUTICAL Co.,Ltd. Registration number: Y2024980043364 |