CN106596799A - Method for detecting glycine and impurities thereof through high-performance liquid chromatography - Google Patents
Method for detecting glycine and impurities thereof through high-performance liquid chromatography Download PDFInfo
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- CN106596799A CN106596799A CN201710050705.8A CN201710050705A CN106596799A CN 106596799 A CN106596799 A CN 106596799A CN 201710050705 A CN201710050705 A CN 201710050705A CN 106596799 A CN106596799 A CN 106596799A
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- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 title claims abstract description 108
- 239000004471 Glycine Substances 0.000 title claims abstract description 51
- 238000000034 method Methods 0.000 title claims abstract description 33
- 239000012535 impurity Substances 0.000 title claims abstract description 20
- 238000004128 high performance liquid chromatography Methods 0.000 title claims abstract description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000007788 liquid Substances 0.000 claims abstract description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910000402 monopotassium phosphate Inorganic materials 0.000 claims abstract description 10
- 235000019796 monopotassium phosphate Nutrition 0.000 claims abstract description 10
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000001514 detection method Methods 0.000 claims description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 239000000243 solution Substances 0.000 abstract description 5
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 abstract description 4
- FYWDUQCSMYWUHV-UHFFFAOYSA-N 3-chloro-5-hydroxypentan-2-one Chemical compound CC(=O)C(Cl)CCO FYWDUQCSMYWUHV-UHFFFAOYSA-N 0.000 abstract description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000010413 mother solution Substances 0.000 abstract description 2
- XKUKSGPZAADMRA-UHFFFAOYSA-N glycyl-glycyl-glycine Chemical compound NCC(=O)NCC(=O)NCC(O)=O XKUKSGPZAADMRA-UHFFFAOYSA-N 0.000 abstract 2
- 238000005915 ammonolysis reaction Methods 0.000 abstract 1
- 229940106681 chloroacetic acid Drugs 0.000 abstract 1
- 108010067216 glycyl-glycyl-glycine Proteins 0.000 abstract 1
- 229940091173 hydantoin Drugs 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 229960002449 glycine Drugs 0.000 description 40
- 239000012071 phase Substances 0.000 description 24
- 235000001014 amino acid Nutrition 0.000 description 8
- 150000001413 amino acids Chemical class 0.000 description 8
- 238000001212 derivatisation Methods 0.000 description 6
- 239000007791 liquid phase Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- XUKUURHRXDUEBC-SXOMAYOGSA-N (3s,5r)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-SXOMAYOGSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- ILRLTAZWFOQHRT-UHFFFAOYSA-N potassium;sulfuric acid Chemical compound [K].OS(O)(=O)=O ILRLTAZWFOQHRT-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- QGQXAMBOYWULFX-LZWSPWQCSA-N 2-morpholin-4-ylethyl (e)-6-(4,6-dihydroxy-7-methyl-3-oxo-1h-2-benzofuran-5-yl)-4-methylhex-4-enoate Chemical compound OC=1C=2C(=O)OCC=2C(C)=C(O)C=1C\C=C(/C)CCC(=O)OCCN1CCOCC1 QGQXAMBOYWULFX-LZWSPWQCSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical class [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 235000019605 sweet taste sensations Nutrition 0.000 description 2
- 238000007445 Chromatographic isolation Methods 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000275 quality assurance Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 239000007785 strong electrolyte Substances 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 238000004448 titration Methods 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for detecting glycine and impurities thereof through high-performance liquid chromatography. The method includes using, by volume, 80-99% of acetonitrile and 1-20% of water as a first mobile phase; using, by volume, 80-99% of 5-30 mmol/L potassium dihydrogen phosphate solution and 1-10% of methyl alcohol as a second mobile phase; determining the glycine in a liquid chromatograph with a C18 chromatographic column. The method is capable of well separating all the impurities of the glycine, especially hydantoin, hydantoic acid and gly-gly-gly, and is good in reproducibility. Compared with the prior art, the method has the advantage that the method is capable of accurately detecting the content of the glycine from glycine mother solutions synthesized by main industrial production methods (chloroacetic acid ammonolysis, Strecker and Hydantion).
Description
Technical field
The present invention relates to organic analyses technical field, and in particular to one kind by high performance liquid chromatography detection glycine and its
The method of impurity.
Background technology
Glycine is that structure is simplest one in 20 members of amino acid series, is that human body must also known as aminoacetic acid
A kind of aminoacid for needing, has in the molecule acid and basic functionality simultaneously, is in aqueous strong electrolyte.Glycine exists
Dissolubility is larger in intensive polar solvent, is substantially insoluble in non-polar solven, and with higher boiling point and fusing point, by water-soluble
The regulation of liquid Acidity of Aikalinity can make glycine that different molecular conformations are presented.
Because the side switch of glycine is a hydrogen atom, it can take up the space that other aminoacid cannot be occupied, such as
As the aminoacid in collagen helix.Under room temperature, aminoacid is white crystal or Light yellow crystals powder, and has uniqueness
Sweet taste, can relax acid, alkali taste, cover and add in food the bitterness of saccharin and strengthen sweet taste.The synthesis technique of glycine is more, main
There are Chloroacetic Aminolysis, apply special rake method and three kinds of glycolylurea method, glycin mother liquid complicated component is synthesized in three kinds of methods, therefore
Certain difficulty is brought to the content of glycine in accurately detection mother solution.
In prior art, the analysis method of several amino acids, such as liquid chromatography, amino-acid analyzer are had been disclosed for
Method, photometry, formol titration and Kjeldahl's method.Wherein, liquid chromatography generally uses the scheme of pre-column derivatization, will
Glycine elder generation derivatization, then makes reactant realize that separation is detected on analytical column, the content of indirect reaction glycine.Though
So column front derivation can relatively free to selective response condition, there is no the restriction of kinetics；And, the by-product of derivatization
Thing can carry out pretreatment to reduce or eliminate interference, easily allow the carrying out of multistep reaction, have more derivatization reagent optional
Select, it is not necessary to complicated instrument and equipment.But, the by-product that derivatization is formed may cause larger difficulty to chromatographic isolation, and
And impurity or Interference Peaks are readily incorporated during derivatization, make sample loss.Additionally, derivative reagent is expensive, complex operation is right
Do not apply in a kind of aminoacid is determined.
The maximum advantage of Kjeldahl's method is that accuracy is high, but because reagent consumption is big, and it is long to determine the cycle, and
Require that other nitride can not be contained in sample, the inaccurate of result is otherwise easily caused on the contrary.
To sum up, the detection method of glycine a kind of easy to operate and that complicated components can be determined is needed.
The content of the invention
For the deficiencies in the prior art, it is desirable to provide glycine a kind of easy to operate and that complicated components can be determined
Detection method.
In order to solve above-mentioned technical problem, the present invention provides one kind by high performance liquid chromatography detection glycine and its impurity
Method, including：
The use of the acetonitrile of volume ratio 80-99% and the water of 1-20% is the first mobile phase；
The use of volume for the concentration of 80-99% is for the potassium dihydrogen phosphate of 5-30mmol/L and the methanol of 1-10%
Two mobile phases；
Glycine is determined in C18 is for the chromatograph of liquid of chromatographic column.
Preferably, the column temperature of the chromatograph of liquid during measure glycine is set to 20-50 DEG C.
Preferably, the wavelength of the chromatograph of liquid during measure glycine is set to as 200-260nm.
Preferably, the sample size for determining the chromatograph of liquid that glycine is is set to 5-15 μ L.
Preferably, the acetonitrile volume content of first mobile phase and the volume content ratio of water are 85-95%：5-15%.
Preferably, the second mobile phase potassium dihydrogen phosphate and methanol volume ratio are 90-96%：4-10%.
Preferably, the column temperature of the chromatograph of liquid during measure glycine is set to 25 DEG C.
Preferably, second mobile phase needs to adjust pH value less than 3.0.
Preferably, second mobile phase is less than 3.0 using phosphoric acid adjustment pH value.
Preferably, second mobile phase is adjusted to pH value for 2.0 using pH value.
The present invention disclose it is a kind of by high performance liquid chromatography detection glycine and its method for impurity, including：Using volume
The water of acetonitrile and 1-20% than 80-99% is the first mobile phase；Using the concentration that volume is 80-99% for 5-30mmol/L's
The methanol of potassium dihydrogen phosphate and 1-10% is the second mobile phase；Sweet ammonia is determined in C18 is for the chromatograph of liquid of chromatographic column
Acid.Compared to prior art, the glycine in utilization high performance liquid chromatography detection synthesis glycin mother liquid involved in the present invention
And the method for impurity.The detection method can efficiently separate the impurity of glycine, particularly realize to glycolylurea (impurity A), sea
Because of sour (impurity B) and the high efficiency separation of two glycylglycines (impurity C).The method separating degree is high, favorable reproducibility, for synthesis
The process detection of glycine and quality assurance have important practical significance.
Description of the drawings
Fig. 1 is conventionally to determine the glycine high-efficient liquid phase chromatogram containing impurity；
Fig. 2 is the high-efficient liquid phase chromatogram of high-purity glycine of present invention detection；
Fig. 3 is the glycine high-efficient liquid phase chromatogram containing impurity of present invention detection.
Specific embodiment
The present invention provides a kind of by high performance liquid chromatography detection glycine and its method for impurity, including：
The use of the acetonitrile of volume ratio 80-99% and the water of 1-20% is the first mobile phase；
The use of volume for the concentration of 80-99% is for the potassium dihydrogen phosphate of 5-30mmol/L and the methanol of 1-10%
Two mobile phases；
Glycine is determined in C18 is for the chromatograph of liquid of chromatographic column.
According to the present invention, for the first mobile phase, the mixed of the acetonitrile of volume ratio 80-99% and the water of 1-20% is preferably used
The volume ratio for closing solution, the acetonitrile and water is more preferably 80-99%：1-20%, more preferably 85-95%：5-15%, it is more excellent
Elect 88-92% as：8-12%.For the second mobile phase, potassium dihydrogen phosphate and methanol volume ratio are 90-96%：4-10%.
The concentration of the potassium dihydrogen phosphate in the second mobile phase is preferably 5-30mmol/L, more preferably 8-25mmol/L, more preferably
For 10-15mmol/L.For the second mobile phase, preferably use phosphoric acid and be adjusted to pH value for 2.0-3.0, more preferably 2.0.
According to the present invention, for chromatographic column is preferably C18,250*4.6mm, 5 μm.Column temperature is preferably controlled in 20-50 DEG C, more
It is preferably controlled in 25-30 DEG C.Wavelength is set to 200-260nm, more preferably 205-210nm.Flow velocity is set to 0.5-2.0mL/
Min, more preferably 1.0-1.5mL/min.
Hereinafter technical scheme is illustrated with specific embodiment.
Embodiment 1
Chromatographic column is C18,250*4.6mm, 5 μm
Column temperature is preferably controlled in 25 DEG C；
Wavelength is adjusted to 210nm；
Flow velocity is arranged on 1.0mL/min；
Sample size is 10 μ L.
First mobile phase is the acetonitrile of 90% volume and 10 volume of water；Second mobile phase is the 20mmol/L of 95% volume
After the methanol mixed of dihydrogen sulfate potassium solution and 5% volume, with sulphuric acid pH value 2.0 is adjusted.
Detection object is high-purity glycine, as a result such as Fig. 2.
Embodiment 2
Chromatographic column is C18,250*4.6mm, 5 μm
Column temperature is preferably controlled in 24 DEG C；
Wavelength is adjusted to 230nm；
Flow velocity is arranged on 1.5mL/min；
Sample size is 9 μ L.
First mobile phase is the water of 100% volume；Second mobile phase is the potassium dihydrogen sulfate of the 20mmol/L of 94% volume
After the methanol mixed of solution and 6% volume, with phosphoric acid pH value 2.0 is adjusted.
Detection object is impure glycine, as a result such as Fig. 1.
Embodiment 3
Chromatographic column is C18,250*4.6mm, 5 μm
Column temperature is preferably controlled in 25 DEG C；
Wavelength is adjusted to 210nm；
Flow velocity is arranged on 1.0mL/min；
Sample size is 10 μ L.
First mobile phase is the acetonitrile of 90% volume and 10 volume of water；Second mobile phase is the 20mmol/L of 95% volume
After the methanol mixed of dihydrogen sulfate potassium solution and 5% volume, with sulphuric acid pH value 2.0 is adjusted.
Detection object is impure glycine, as a result such as Fig. 3.
Comparative example 1
Fig. 1 be using traditional method measure come glycine design sketch, from embodiment 1, embodiment 2 and the figure of embodiment 3,
It can be seen that, conventionally determine the glycine high-efficient liquid phase chromatogram (Fig. 1) containing impurity, glycine and glycolylurea
(impurity A), hydantoic acid (impurity B) and two glycylglycines (impurity C) peak shape overlapping, it is impossible to distinguish；According to the present invention
Determine high-purity glycine, the glycine high-efficient liquid phase chromatogram (Fig. 2, Fig. 3) containing impurity, glycine and impurity A, impurity B and
Each peak shape is clear for impurity C, realizes and efficiently separates.
The present invention discloses a kind of detection method of glycine, including：Using the acetonitrile and 1-20% of volume ratio 80-99%
Water is the first mobile phase；Using the potassium dihydrogen phosphate and 1-10% that the concentration that volume is 80-99% is 5-30mmol/L
Methanol is the second mobile phase；Glycine is determined in C18 is for the chromatograph of liquid of chromatographic column.The present invention is by selecting suitable stream
Dynamic phase determines glycine with chromatographic column, as a result shows, compared with prior art, the present invention can accurately detect wherein sweet ammonia
Acid content.
The foregoing description of the disclosed embodiments, enables professional and technical personnel in the field to realize or using the present invention.
Various modifications to these embodiments will be apparent for those skilled in the art, as defined herein
General Principle can be realized without departing from the spirit or scope of the present invention in other embodiments kind.Therefore, the present invention
It is not intended to be limited to the embodiments shown herein, and is to fit to principles disclosed herein and features of novelty is consistent
Most wide scope.
Claims (10)
1. it is a kind of by high performance liquid chromatography detection glycine and its method for impurity, it is characterised in that to include：
The use of the acetonitrile of volume ratio 80-99% and the water of 1-20% is the first mobile phase；
The use of the methanol of potassium dihydrogen phosphate and 1-10% that the concentration that volume is 80-99% is 5-30mmol/L is second
Dynamic phase；
Glycine is determined in C18 is for the chromatograph of liquid of chromatographic column.
2. method according to claim 1, it is characterised in that the column temperature of the chromatograph of liquid during measure glycine sets
It is set to 20-50 DEG C.
3. method according to claim 2, it is characterised in that the wavelength of the chromatograph of liquid during measure glycine sets
It is set to as 200-260nm.
4. method according to claim 3, it is characterised in that the sample size of the chromatograph of liquid that the measure glycine is
It is set to 5-15 μ L.
5. the method according to any one of Claims 1-4, it is characterised in that the acetonitrile volume of first mobile phase contains
Amount is 85-95% with the volume content ratio of water：5-15%.
6. method according to claim 5, it is characterised in that the second mobile phase potassium dihydrogen phosphate and methanol body
Product is than being 90-96%：4-10%.
7. method according to claim 6, it is characterised in that the column temperature of the chromatograph of liquid during measure glycine sets
It is set to 25 DEG C.
8. method according to claim 7, it is characterised in that second mobile phase needs to adjust pH value and is less than 3.0.
9. method according to claim 8, it is characterised in that second mobile phase is less than using phosphoric acid adjustment pH value
3.0。
10. method according to claim 9, it is characterised in that second mobile phase is adjusted to pH value and is using pH value
2.0。
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| CN201710050705.8A CN106596799A (en) | 2017-01-20 | 2017-01-20 | Method for detecting glycine and impurities thereof through high-performance liquid chromatography |
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| CN110988154A (en) * | 2019-11-15 | 2020-04-10 | 天津市海诺德工贸有限公司 | Method for detecting glycine content in hemodialysis solution |
| CN117517541A (en) * | 2023-11-13 | 2024-02-06 | 重庆医科大学 | Method for measuring concentration of glycylglycine in blood plasma |
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| CN110988154A (en) * | 2019-11-15 | 2020-04-10 | 天津市海诺德工贸有限公司 | Method for detecting glycine content in hemodialysis solution |
| CN117517541A (en) * | 2023-11-13 | 2024-02-06 | 重庆医科大学 | Method for measuring concentration of glycylglycine in blood plasma |
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