CN112881571A - Chiral detection method of Fmoc-L-Hyp (tbu) -OH and isomers thereof by high performance liquid chromatography - Google Patents
Chiral detection method of Fmoc-L-Hyp (tbu) -OH and isomers thereof by high performance liquid chromatography Download PDFInfo
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- CN112881571A CN112881571A CN202110232616.1A CN202110232616A CN112881571A CN 112881571 A CN112881571 A CN 112881571A CN 202110232616 A CN202110232616 A CN 202110232616A CN 112881571 A CN112881571 A CN 112881571A
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- WPBXBYOKQUEIDW-VFNWGFHPSA-N (2s,4r)-1-(9h-fluoren-9-ylmethoxycarbonyl)-4-[(2-methylpropan-2-yl)oxy]pyrrolidine-2-carboxylic acid Chemical compound C1[C@H](OC(C)(C)C)C[C@@H](C(O)=O)N1C(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21 WPBXBYOKQUEIDW-VFNWGFHPSA-N 0.000 title claims abstract description 43
- 238000001514 detection method Methods 0.000 title claims abstract description 27
- 238000004128 high performance liquid chromatography Methods 0.000 title claims abstract description 20
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000010828 elution Methods 0.000 claims abstract description 6
- 238000010606 normalization Methods 0.000 claims abstract description 4
- 239000000243 solution Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 13
- 238000010829 isocratic elution Methods 0.000 claims description 12
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 238000010586 diagram Methods 0.000 description 5
- 229960002591 hydroxyproline Drugs 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 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 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 108010062049 chirobiotic T Proteins 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- BJBUEDPLEOHJGE-UHFFFAOYSA-N (2R,3S)-3-Hydroxy-2-pyrolidinecarboxylic acid Natural products OC1CCNC1C(O)=O BJBUEDPLEOHJGE-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 241000521257 Hydrops Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 208000016247 Soft tissue disease Diseases 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000000490 cosmetic additive Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- RFNODQARGNZURK-UHFFFAOYSA-N methyl 2-acetamidoacetate Chemical compound COC(=O)CNC(C)=O RFNODQARGNZURK-UHFFFAOYSA-N 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000004223 radioprotective effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 235000019605 sweet taste sensations Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- BJBUEDPLEOHJGE-IMJSIDKUSA-N trans-3-hydroxy-L-proline Chemical class O[C@H]1CC[NH2+][C@@H]1C([O-])=O BJBUEDPLEOHJGE-IMJSIDKUSA-N 0.000 description 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N trans-4-Hydroxy-L-proline Natural products O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000029663 wound healing Effects 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
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
-
- 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
- G01N30/62—Detectors specially adapted therefor
- G01N30/74—Optical detectors
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- 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)
- Spectroscopy & Molecular Physics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a chiral detection method of Fmoc-L-Hyp (tbu) -OH and isomers thereof by high performance liquid chromatography, which comprises the following steps: preparing a mobile phase A from an ion pair solution of n-hexane and 0.1% TFA according to a certain proportion; preparing mobile phase B from ion pair solution of isopropanol and 0.1% TFA according to a certain proportion; injecting a solution to be detected, and performing equal gradient elution on the chromatographic column by using the mobile phase A and the mobile phase B; and recording a chromatogram, and calculating the chiral purity of Fmoc-Hyp (tbu) -OH by adopting an area normalization method.
Description
Technical Field
The invention relates to the technical field of detection of organic compounds, in particular to a chiral detection method of Fmoc-L-Hyp (tbu) -OH and isomers thereof by high performance liquid chromatography.
Background art:
hydroxyproline (Hydroxyproline, Hydrop), also known as trans-4-hydroxy-L-proline, is the main component of collagen and does not belong to 20 common amino acids. In recent years, research and development of Hyp have attracted extensive attention in the pharmaceutical, biochemical, food and cosmetic industries, and the like. It can be used as cosmetic additive, and has antioxidant and radioprotective effects; it has the function of losing weight and is expected to become an ideal weight-losing medicine; has multiple physiological functions and unique biological activity, can be used as a medicament for treating various soft tissue diseases, such as damaged connective tissues, rheumatoid arthritis and the like, and can accelerate wound healing and treat various skin diseases.
The molecular formula of Hyp is C5H9NO3, and the molecular weight is 131.13. Usually in the form of crystalline powder or white flakes, and has a special sweet taste of bitter taste. Melting point 274 deg.C, readily soluble in water (25 deg.C, 36.1%) and slightly soluble in ethanol. Hydroxyproline has four isomers, including two isomers of 4-hydroxyproline and two isomers of 3-hydroxyproline.
The separation of enantiomers is of great importance in biochemistry, the pharmaceutical industry and modern stereoselective organic synthesis. Enantiomers of chemical drugs containing chiral factors have significant differences in pharmacological activity, metabolic processes and toxicity in the human body. The study of chiral drugs has become one of the major directions in the international research of new drugs. Most drugs are composed of chiral molecules, two of which may have significantly different biological activities. The drug molecules must match the molecular geometry of the receptor (the reacting substance) to exert the desired drug effect, just as the right hand can only carry the right glove. Thus, often only one of the two isomers is effective, the other is ineffective or even detrimental, and the four isomers of hydroxyproline are more difficult to separate chirally.
Disclosure of Invention
The invention aims to provide a chiral detection method of Fmoc-L-Hyp (tbu) -OH and an isomer thereof by using a high performance liquid chromatography, so as to overcome the defect that the prior art lacks a chiral detection method of Fmoc-L-Hyp (tbu) -OH and an isomer thereof.
A chiral detection method of Fmoc-L-Hyp (tbu) -OH and isomers thereof by high performance liquid chromatography, which comprises the following steps:
preparing a mobile phase A from an ion pair solution of n-hexane and 0.1% TFA according to a certain proportion;
preparing mobile phase B from ion pair solution of isopropanol and 0.1% TFA according to a certain proportion;
injecting a solution to be detected, and performing equal gradient elution on the chromatographic column by using the mobile phase A and the mobile phase B;
recording the chromatogram, and calculating the chiral purity of Fmoc-Hyp (tbu) -OH by using an area normalization method.
Furthermore, the n-hexane accounts for 60-85% by volume, the isopropanol accounts for 15-35% by volume, and the ion pair solution of 0.1% TFA accounts for 0.02-1.5% by volume.
Further, the chromatographic column used comprises one or more of chiralpak IC, chiralcel OD-H, chiralpak IA, chiralpak IB and chiralotic R.
Further, the column temperature of the isocratic elution is 20-50 ℃.
Furthermore, the injection concentration of the isocratic elution is controlled to be 0.25-1.5 mg/ml.
Furthermore, the detection wavelength of the ultraviolet detector during the isocratic elution is 210-240 nm.
Further, the detection wavelength of the ultraviolet detector during the isocratic elution is 220 nm.
Further, the flow rate of the mobile phase during the isocratic elution is 0.5-1.5 ml/min.
Further, the flow rate of the mobile phase at the time of the isocratic elution was 0.7 ml/min.
Further, the solution to be tested comprises one or a combination of Fmoc-L-Hyp (tbu) -OH solution, isomer Fmoc-D-Hyp (tbu) -OH solution, isomer Fmoc-L-Cis-Hyp (tbu) -OH solution and isomer Fmoc-D-Cis-Hyp (tbu) -OH solution.
The invention has the advantages that: the novel chiral detection method for Fmoc-L-Hyp (tbu) -OH and isomers thereof is provided, the detection speed is high, the result is accurate, the method steps are simple, the operation is convenient, and the method has a wide application prospect.
Drawings
FIG. 1 is a schematic diagram showing the molecular structure of Fmoc-L-Hyp (tbu) -OH in the present invention.
FIG. 2 is a schematic diagram showing the molecular structure of Fmoc-L-Hyp (tbu) -OH isomer in the present invention.
FIG. 3 is a schematic diagram of high performance liquid chromatography of comparative example 1 in the present invention.
FIG. 4 is a schematic diagram of high performance liquid chromatography of comparative example 2 in the present invention.
FIG. 5 is a schematic diagram of high performance liquid chromatography of comparative example 3 in the present invention.
FIG. 6 is a schematic high performance liquid chromatography of example 1 of the present invention.
Detailed Description
In order to make the technical means, the creation characteristics, the achievement purposes and the effects of the invention easy to understand, the invention is further described with the specific embodiments.
As shown in fig. 1 to 6, a chiral detection method of Fmoc-L-hyp (tbu) -OH and isomers thereof by high performance liquid chromatography, the method comprising the steps of:
the method comprises the following steps: preparing a mobile phase A from an ion pair solution of n-hexane and 0.1% TFA according to a certain proportion;
step two: preparing mobile phase B from ion pair solution of isopropanol and 0.1% TFA according to a certain proportion;
wherein the ion pair solution containing 0.1% TFA has a volume content of 0.02-1.5%, n-hexane has a volume content of 60-85%, and isopropanol has a volume content of 15-35%;
step three: injecting a solution to be detected, and performing equal gradient elution on a chromatographic column by using a mobile phase A and a mobile phase B, wherein the column temperature of the gradient elution is 20-50 ℃, the sample injection concentration is controlled to be 0.25-1.5 mg/ml, the flow rate of the mobile phase is 0.5-1.5 ml/min, and the used chiral columns comprise chiralpak IC, chiralcel OD-H, chiralpak IA, chiralpak IB and chiralic R;
step four: recording a chromatogram, and calculating the chiral purity of Fmoc-Hyp (tbu) -OH by adopting an area normalization method;
the detection wavelength of the ultraviolet detector during the isocratic elution is 210-240 nm, the preferable detection wavelength is 220nm, and the preferable flow rate of the mobile phase is 0.7 ml/min.
The scheme of the invention is further illustrated below by examples and comparative examples:
comparative example 1:
the chromatographic conditions adopted are as follows:
a chromatographic column: 4.6 x 250mm, CHIROBIOTIC T column;
mobile phase: MeOH: AcOH: TEA ═ 100:0.03: 0.03;
wavelength: 220nm sample configuration, 5mg/10ml mobile phase;
sample introduction amount: 10 ul;
flow rate: 0.6 ml/min;
a mixed solution of Fmoc-L-Hyp (tbu) -OH and the isomers Fmoc-D-Hyp (tbu) -OH, Fmoc-L-Cis-Hyp (tbu) -OH, Fmoc-D-Cis-Hyp (tbu) -OH was injected, and 3 isomers were not separated from each other as shown in FIG. 3.
Comparative example 2:
the chromatographic conditions adopted are as follows:
chromatography column 4.6 × 250mm, CHIROBIOTIC T column;
mobile phase A100% H2O;
mobile phase B, MeOH, AcOH, TEA 100:0.03: 0.03;
equal gradient: a and B are 50: 50;
the wavelength is 220 nm;
sample preparation, 5mg/10ml mobile phase;
the sample injection amount is 5 ul;
the flow rate is 0.4 ml/min;
a mixed solution of Fmoc-L-Hyp (tbu) -OH and the isomers Fmoc-D-Hyp (tbu) -OH, Fmoc-L-Cis-Hyp (tbu) -OH, Fmoc-D-Cis-Hyp (tbu) -OH was injected, and 2 isomers were not separated from each other as shown in FIG. 4.
Comparative example 3:
the chromatographic conditions adopted are as follows:
chromatography column 4.6 × 250mm, chiralpak IC;
mobile phase a phase 0.1% TFA in 100% Hex;
mobile phase B phase 0.1% TFA in 100% IPA;
an equal gradient A: B ═ 90: 10;
the wavelength is 220 nm;
sample preparation 5mg/10ml IPA;
the sample amount is 10 ul;
the flow rate is 0.8 ml/min;
a mixed solution of Fmoc-L-Hyp (tbu) -OH and the isomers Fmoc-D-Hyp (tbu) -OH, Fmoc-L-Cis-Hyp (tbu) -OH, Fmoc-D-Cis-Hyp (tbu) -OH was injected, and 1 isomer was not separated from FIG. 5.
Example 1:
the chromatographic conditions adopted are as follows:
chromatography column 4.6 × 250mm, chiralpak IC;
mobile phase a phase 0.1% TFA in 100% Hex;
mobile phase B phase 0.1% TFA in 100% IPA;
an equal gradient A: B ═ 80: 20;
the wavelength is 220 nm;
sample preparation 5mg/10ml IPA;
the sample amount is 10 ul;
the flow rate is 0.7 ml/min;
the mixed solution of Fmoc-L-Hyp (tbu) -OH and the isomers Fmoc-D-Hyp (tbu) -OH, Fmoc-L-Cis-Hyp (tbu) -OH, Fmoc-D-Cis-Hyp (tbu) -OH was injected, and the four isomers were successfully separated as shown in FIG. 6.
And respectively injecting Fmoc-L-Hyp (tbu) -OH and an isomer Fmoc-D-Hyp (tbu) -OH, an isomer Fmoc-L-Cis-Hyp (tbu) -OH, an isomer Fmoc-D-Cis-Hyp (tbu) -OH, determining peak emergence time, obtaining Fmoc-L-Hyp (tbu) -OH about 12.9min, Fmoc-D-Hyp (tbu) -OH about 15min, an isomer Fmoc-L-Cis-Hyp (tbu) -OH about 21min and an isomer Fmoc-D-Cis-Hyp (tbu) -OH about 40 min.
The method can well separate four isomers of Fmoc-L-Hyp (tbu) -OH, thereby effectively controlling the chiral purity of Fmoc-L-Hyp (tbu) -OH.
It will be appreciated by those skilled in the art that the invention may be embodied in other specific forms without departing from the spirit or essential characteristics thereof. The embodiments disclosed above are therefore to be considered in all respects as illustrative and not restrictive. All changes which come within the scope of or equivalence to the invention are intended to be embraced therein.
Claims (10)
1. A chiral detection method of Fmoc-L-Hyp (tbu) -OH and isomers thereof by high performance liquid chromatography is characterized by comprising the following steps:
preparing a mobile phase A from an ion pair solution of n-hexane and 0.1% TFA according to a certain proportion;
preparing mobile phase B from ion pair solution of isopropanol and 0.1% TFA according to a certain proportion;
injecting a solution to be detected, and performing equal gradient elution on the chromatographic column by using the mobile phase A and the mobile phase B;
recording the chromatogram, and calculating the chiral purity of Fmoc-Hyp (tbu) -OH by using an area normalization method.
2. The method for chiral detection of Fmoc-L-Hyp (tbu) -OH and its isomers by high performance liquid chromatography according to claim 1, wherein: the volume content of the n-hexane is 60-85%, the volume content of the isopropanol is 15-35%, and the volume content of the 0.1% TFA ion pair solution is 0.02-1.5%.
3. The method for chiral detection of Fmoc-L-Hyp (tbu) -OH and its isomers by high performance liquid chromatography as claimed in claim 2, wherein: the chromatographic column comprises one or more of chiralpak IC, chiralcel OD-H, chiralpak IA, chiralpak IB and chiralotic R.
4. The method of claim 3 for chiral detection of Fmoc-L-Hyp (tbu) -OH and its isomers by HPLC, wherein: the column temperature of the isocratic elution is 20-50 ℃.
5. The chiral detection method of Fmoc-L-Hyp (tbu) -OH and its isomers by high performance liquid chromatography according to any one of claims 1 to 4, wherein: the sample injection concentration of the isocratic elution is controlled to be 0.25-1.5 mg/ml.
6. The method of claim 5 for chiral detection of Fmoc-L-Hyp (tbu) -OH and its isomers by HPLC, wherein: the detection wavelength of the ultraviolet detector during the isocratic elution is 210-240 nm.
7. The method of claim 6 for chiral detection of Fmoc-L-Hyp (tbu) -OH and its isomers by HPLC, wherein: the detection wavelength of the ultraviolet detector during the isocratic elution is 220 nm.
8. The method of claim 7 for chiral detection of Fmoc-L-Hyp (tbu) -OH and its isomers by HPLC, wherein: the flow rate of the mobile phase in the equal gradient elution is 0.5-1.5 ml/min.
9. The method of claim 8 for chiral detection of Fmoc-L-Hyp (tbu) -OH and its isomers by HPLC, wherein: the flow rate of the mobile phase in the isocratic elution is 0.7 ml/min.
10. The method of claim 9 for chiral detection of Fmoc-L-hyp (tbu) -OH and its isomers by hplc, comprising: the solution to be tested comprises one or more of Fmoc-L-Hyp (tbu) -OH solution, isomer Fmoc-D-Hyp (tbu) -OH solution, isomer Fmoc-L-Cis-Hyp (tbu) -OH solution and isomer Fmoc-D-Cis-Hyp (tbu) -OH solution.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115541733A (en) * | 2022-07-14 | 2022-12-30 | 南京锐志生物医药有限公司 | Method for measuring protected amino acid enantiomer by reverse phase chromatography |
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| CN111871401A (en) * | 2020-07-31 | 2020-11-03 | 天津大学 | Polypeptide supermolecule chiral filler for high performance liquid chromatography, preparation method and application |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115541733A (en) * | 2022-07-14 | 2022-12-30 | 南京锐志生物医药有限公司 | Method for measuring protected amino acid enantiomer by reverse phase chromatography |
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