CN107892717A - A kind of method of purifying Suo Malu peptides - Google Patents
A kind of method of purifying Suo Malu peptides Download PDFInfo
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- CN107892717A CN107892717A CN201711474148.9A CN201711474148A CN107892717A CN 107892717 A CN107892717 A CN 107892717A CN 201711474148 A CN201711474148 A CN 201711474148A CN 107892717 A CN107892717 A CN 107892717A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/605—Glucagons
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Abstract
The present invention is a kind of method of purifying Suo Malu peptides, and its step is as follows：Suo Malu peptide crude products are dissolved in dilute ammonia solution and obtain the thick peptide aqueous solution；Filtering, filtrate carry out HPLC linear gradient elutions by stationary phase of inverted polymer chromatograph packing material；Collect the cut containing Suo Malu peptides；Revolving removes partial acetonitrile；Obtain purification solution of Suo Malu peptides；HPLC linear elutions are carried out by stationary phase of eight alkyl silane bonded silica gels；Collect the cut containing Suo Malu peptides；Revolving removes partial acetonitrile；Obtain Suo Malu peptide purification solution.The inventive method, once inverted polymer chromatograph packing material selected by purifying, can bear strong alkali solution.And applied sample amount of Suo Malu peptides is big, high income, purity height.Purifying number can be so reduced, reduces loss, it is cost-effective.It is secondarily purified using eight alkyl silane bonded silica gels as stationary phase with selected mobile phase be combined, can once receive more than 99%, maximum single miscellaneous 0.15% product.
Description
Technical field
The present invention relates to a kind of purification process of polypeptide compound, more particularly to a kind of method of purifying Suo Malu peptides.
Background technology
Chinese name：Suo Malu peptides
English name：Sermaglutide
Peptide sequence is：
H-His-Aib-Glu-Gly-Thr-Phe-Thr-Ser-Asp-Val-Ser-Ser-Tyr-Leu-Glu-Gly-Gln-
Ala-Ala-Lys(Octadecanedioic-g-Glu-PEG2-PEG2)-Glu-Phe-Ile-Ala-Trp-Leu-Val-Arg-
Gly-Arg-Gly-OH
The New-type long-acting GLP-1 analogs that Suo Malu peptides are developed by Novo Nordisk Co., Ltd of Denmark, from amino acid sequence, peptide sequence
2 are alpha-non-natural amino acid aminoisobutyric acid, and the Lys side-chain amino groups of peptide sequence 20 have passed through PEG, γ-Glu and octadecane diacid
Modification.Compared with Liraglutide, the Suo Malu peptides hydrophily enhancing after modification, suppress the hydrolysis of DPP-4 enzymes, extend biology half
Decline the phase, long-acting reduction blood glucose, promote pancreatic cell regeneration, it is extensive to extend a variety of effects, the application prospects such as gastric emptying.
Diabetes（Diabetes Mellitus, DM）It is a kind of global high morbidity, countries in the world type II diabetes is suffered from
Sick rate sharply increases, and the trend that type II diabetes sharply increases in nearly 30 or five ten years is still difficult to alleviate.The result of WHO predictions is such as
Under：Diabetic's number in 1994 be within 1.20 hundred million, 1997 be within 1.35 hundred million, 2000 1.75 hundred million, 2010 be 2.39 hundred million,
300,000,000 will be broken through within 2025, this numeral will be close to 600,000,000 by 2035.Wherein 80% lives in middle and low income country.Diabetes relate to
And each system of whole body, the labour capacity of people is had a strong impact on, and threaten the life security of people.
Suo Malu peptides are the novel therapeutic diabetes medicaments that Novo Nordisk Co., Ltd is carrying out phase iii clinical trial, are noted weekly
It is 1.0mg to penetrate dose, and curative effect is extremely outstanding, while also carries out oral Suo Malu peptide formulations（40mg specifications）Clinical examination
Test, and achieve certain effect, if the oral formulations of Suo Malu peptides are succeeded in developing, the life of diabetic will be improved greatly
Quality.Therefore, the purification process for researching and developing Suo Malu peptides has great importance.
The content of the invention
The technical problems to be solved by the invention are in view of the shortcomings of the prior art, there is provided one kind purifying thick peptide of Suo Malu peptides
Method, it is not high to solve Suo Malu peptide finished product purity, the problem of yield is low.
The technical problems to be solved by the invention are realized by following technical scheme.The present invention is a kind of purifying
The method of Suo Malu peptides, is characterized in, its step is as follows：Suo Malu peptide crude products are dissolved in dilute ammonia solution to obtain thick peptide water-soluble
Liquid；Filtering, filtrate carry out HPLC linear gradients using inverted polymer chromatograph packing material as stationary phase, using acetic acid and acetonitrile as mobile phase
Elution；The cut containing Suo Malu peptides is collected, revolving removes partial acetonitrile；Obtain purification solution of Suo Malu peptides；Suo Malu
Purification solution of peptide is using eight alkyl silane bonded silica gels as stationary phase, to adjust pH trifluoroacetic acid aqueous solution with triethylamine, contain
There is trifluoroacetic acetonitrile solution to carry out HPLC linear elutions for mobile phase；Collect the cut containing Suo Malu peptides；Revolving removes
Partial acetonitrile；Obtain Suo Malu peptide purification solution.
A kind of method of purifying Suo Malu peptides of the present invention, its further preferred technical scheme steps are as follows：
（1）Suo Malu peptide crude products are dissolved in 8% dilute ammonia solution and obtain the thick peptide aqueous solution；
（2）The thick peptide aqueous solution 0.22um membrane filtrations of Suo Malu peptides are taken, it is standby to collect filtrate；
（3）Filtrate is taken, using inverted polymer chromatograph packing material as stationary phase；Detection wavelength is that 230nm progress HPLC linear gradients are washed
It is de-；Mobile phase A is：0.5% acetic acid, ammoniacal liquor adjust the aqueous solution of pH=7.6, and Mobile phase B is：Pure acetonitrile；Gradient Initial Gradient B
Phase 5% keeps 5min, then 60min to 45%；Collect the cut containing Suo Malu peptides；
（4）With rotary evaporator water bath temperature at 30 ~ 35 DEG C, vacuum removes partial acetonitrile below -0.09MPa；Obtain rope
Purification solution of agate Shandong peptide；It is meta-alkalescence to obtain purification solution of Suo Malu peptides；
（5）Purification solution of Suo Malu peptides is taken, using eight alkyl silane bonded silica gels as stationary phase；Detection wavelength is entered for 230nm
Row HPLC linear elutions；0.2% trifluoracetic acid, it is A phases that triethylamine, which adjusts the aqueous solution of pH=2.5, contains 0.1% trifluoroacetic second
Nitrile solution is B phases；Gradient Initial Gradient B phases 5% keep 5min, and then 60min to 55%, collects evaporating containing Suo Malu peptides
Point；
（6）With rotary evaporator water bath temperature at 30 ~ 35 DEG C, vacuum removes partial acetonitrile below -0.09MPa；Obtain rope
Agate Shandong peptide purification solution.Suo Malu peptide purifications solution is obtained as acidity.
The method of purifying Suo Malu peptides of the present invention, its further preferred technical scheme are：Rotary evaporator water
Bath temperature is at 30 ~ 35 DEG C.
Compared with prior art, the inventive method has advantages below：
The inventive method, once inverted polymer chromatograph packing material selected by purifying, can bear strong alkali solution.And Suo Malu peptides
One time applied sample amount is big, high income, and purity is high.Purifying number can be so reduced, reduces loss, it is cost-effective.It is secondarily purified with
Eight alkyl silane bonded silica gels be stationary phase with selected mobile phase be combined, can once receive more than 99%, be maximum single miscellaneous
0.15% product.
Brief description of the drawings
Fig. 1 is Liraglutide crude product chromatogram in embodiment 4；
Fig. 2 is the product chromatogram of Liraglutide once after purification in embodiment 4；
Product chromatograms of the Fig. 3 for Liraglutide in embodiment 4 after secondarily purified.
Embodiment
Concrete technical scheme of the invention described further below, in order to which those skilled in the art is further understood that
The present invention, without forming the limitation to its right.
Embodiment 1, a kind of method of purifying Suo Malu peptides, step are as follows：
（1）2g Suo Malu peptide crude products are dissolved in 8% dilute ammonia solution, 0.22um membrane filtrations are used after being completely dissolved.Collect filtering
The thick peptide aqueous solution afterwards is standby；
（2）First step HPLC is purified
Chromatographic condition：Chromatographic column：Inverted polymer chromatograph packing material, the diameter and length of chromatographic column are：30*250mm.Mobile phase A：
0.5% acetic acid, ammoniacal liquor adjust the aqueous solution of pH=7.6.Mobile phase B：Acetonitrile.Flow velocity：20mL/min Detection wavelengths are：230nm.On
Sample amount：1.5g.Gradient Initial Gradient B phases 5% keep 5min, then 60min to 45%.Collect containing Suo Malu peptide samples
Cut.With rotary evaporator water bath temperature at 30 ~ 35 DEG C, vacuum removes partial acetonitrile below -0.09MPa；Obtain Suo Ma
Purification solution of Shandong peptide.
（3）Second step HPLC is purified
Chromatographic condition：Chromatographic column：Eight alkyl silane bonded silica gels, the diameter and length of chromatographic column are：30*250mm.Mobile phase A：
0.2% trifluoracetic acid, triethylamine adjust the aqueous solution of pH=2.5.Mobile phase B：Contain 0.1% trifluoroacetic acetonitrile solution.Flow velocity：
20mL/min Detection wavelengths are：230nm.Applied sample amount：0.8g.Gradient Initial Gradient B phases 5% keep 5min, then
60min to 55%.Collect the cut containing Suo Malu peptides.With rotary evaporator water bath temperature at 30 ~ 35 DEG C, vacuum-
Below 0.09MPa removes partial acetonitrile.Obtain Suo Malu peptide purification solution.
Embodiment 2, a kind of method of purifying Suo Malu peptides, step are as follows：
（1）5g Suo Malu peptide crude products are dissolved in 8% dilute ammonia solution, 0.22um membrane filtrations are used after being completely dissolved.Collect filtering
The thick peptide aqueous solution afterwards is standby.
（2）First step HPLC is purified
Chromatographic condition：Chromatographic column：Inverted polymer chromatograph packing material, the diameter and length of chromatographic column are：50*250mm.Mobile phase A：
0.5% acetic acid, ammoniacal liquor adjust the aqueous solution of pH=7.6.Mobile phase B：Acetonitrile.Flow velocity：60mL/min Detection wavelengths are：230nm.On
Sample amount：4g.Gradient Initial Gradient B phases 5% keep 5min, then 60min to 45%.Collect the cut containing Suo Malu peptides.
With rotary evaporator water bath temperature at 30 ~ 35 DEG C, vacuum removes partial acetonitrile below -0.09MPa.Obtain Suo Malu peptides one
Secondary purification solution.
（3）Second step HPLC is purified
Chromatographic condition：Chromatographic column：Eight alkyl silane bonded silica gels, the diameter and length of chromatographic column are：30*250mm.Mobile phase A：
0.2% trifluoracetic acid, triethylamine adjust the aqueous solution of pH=2.5.Mobile phase B：Contain 0.1% trifluoroacetic acetonitrile solution.Flow velocity：
60mL/min Detection wavelengths are：230nm.Applied sample amount：2.2g.Gradient Initial Gradient B phases 5% keep 5min, then
60min to 55%.Collect the cut containing Suo Malu peptides.With rotary evaporator water bath temperature at 30 ~ 35 DEG C, vacuum-
Below 0.09MPa removes partial acetonitrile.Obtain Suo Malu peptide purification solution.
Embodiment 3, a kind of method of purifying Suo Malu peptides, step are as follows：
（1）20g Suo Malu peptide crude products are dissolved in 8% dilute ammonia solution, 0.22um membrane filtrations are used after being completely dissolved.Collected
The thick peptide aqueous solution after filter is standby.
（2）First step HPLC is purified
Chromatographic condition：Chromatographic column：Inverted polymer chromatograph packing material, the diameter and length of chromatographic column are：100*250mm.Mobile phase
A：0.5% acetic acid, ammoniacal liquor adjust the aqueous solution of pH=7.6.Mobile phase B：Acetonitrile.Flow velocity：200mL/min Detection wavelengths are：
230nm.Applied sample amount：16g.Gradient Initial Gradient B phases 5% keep 5min, then 60min to 45%.Collect containing Suo Malu
The cut of peptide.With rotary evaporator water bath temperature at 30 ~ 35 DEG C, vacuum removes partial acetonitrile below -0.09MPa.Obtain
Purification solution of Suo Malu peptides.
（3）Second step HPLC is purified
Chromatographic condition：Chromatographic column：Eight alkyl silane bonded silica gels, the diameter and length of chromatographic column are：30*250mm.Mobile phase A：
0.2% trifluoracetic acid, triethylamine adjust the aqueous solution of pH=2.5.Mobile phase B：Contain 0.1% trifluoroacetic acetonitrile solution.Flow velocity：
200mL/min Detection wavelengths are：230nm.Applied sample amount：8g.Gradient Initial Gradient B phases 5% keep 5min, then 60min
To 55%.Collect the cut containing Suo Malu peptides.With rotary evaporator water bath temperature at 30 ~ 35 DEG C, vacuum -0.09MPa with
Lower removing partial acetonitrile.Obtain Suo Malu peptide purification solution.
Embodiment 4, a kind of method of purifying Suo Malu peptides, step are as follows：
（1）60g Suo Malu peptide crude products are dissolved in 8% dilute ammonia solution, 0.45um membrane filtrations are used after being completely dissolved.Collected
The thick peptide aqueous solution after filter is standby.Fig. 1 is Liraglutide crude product chromatogram；
（2）First step HPLC is purified
Chromatographic condition：Chromatographic column：Inverted polymer chromatograph packing material, the diameter and length of chromatographic column are：150*250mm.Mobile phase
A：0.5% acetic acid, ammoniacal liquor adjust the aqueous solution of pH=7.6.Mobile phase B：Acetonitrile.Flow velocity：600mL/min Detection wavelengths are：
230nm.Applied sample amount：37g.Gradient Initial Gradient B phases 5% keep 5min, then 60min to 45%.Collect containing Suo Malu
The cut of peptide.With rotary evaporator water bath temperature at 30 ~ 35 DEG C, vacuum removes partial acetonitrile below -0.09MPa.Obtain
Purification solution of Suo Malu.Fig. 2 is the product chromatogram of Liraglutide once after purification.
（3）Second step HPLC is purified
Chromatographic condition：Chromatographic column：Eight alkyl silane bonded silica gels, the diameter and length of chromatographic column are：30*250mm.Mobile phase A：
0.2% trifluoracetic acid, triethylamine adjust the aqueous solution of pH=2.5.Mobile phase B：Contain 0.1% trifluoroacetic acetonitrile solution.Flow velocity：
600mL/min Detection wavelengths are：230nm.Applied sample amount：20g.Gradient Initial Gradient B phases 5% keep 5min, then
60min to 55%.Collect the cut containing Suo Malu peptides.With rotary evaporator water bath temperature at 30 ~ 35 DEG C, vacuum-
Below 0.09MPa removes partial acetonitrile.Obtain Suo Malu peptide purification solution.Product colors of the Fig. 3 for Liraglutide after secondarily purified
Spectrogram.
Described above is the preferred embodiment of the present invention, it should be pointed out that is come for those skilled in the art
Say, some improvements and modifications made under the premise without departing from the principles of the invention, these improvements and modifications also should be regarded as this hair
Bright protection domain.
Claims (3)
- A kind of 1. method of purifying Suo Malu peptides, it is characterised in that its step is as follows：It is molten that Suo Malu peptide crude products are dissolved in weak aqua ammonia The thick peptide aqueous solution is obtained in liquid；Filtering, filtrate using inverted polymer chromatograph packing material as stationary phase, using acetic acid and acetonitrile as mobile phase Carry out HPLC linear gradient elutions；The cut containing Suo Malu peptides is collected, revolving removes partial acetonitrile；Obtain Suo Malu peptides once Purification solution；Purification solution of Suo Malu peptides is using eight alkyl silane bonded silica gels as stationary phase, to adjust the three of pH with triethylamine Fluorine aqueous acetic acid, containing trifluoroacetic acetonitrile solution be mobile phase carry out HPLC linear elutions；Collect containing Suo Malu peptides Cut；Revolving removes partial acetonitrile；Obtain Suo Malu peptide purification solution.
- 2. the method for purifying Suo Malu peptides according to claim 1, it is characterised in that it is comprised the following steps that：Suo Malu peptide crude products are dissolved in 8% dilute ammonia solution and obtain the thick peptide aqueous solution；The thick peptide aqueous solution 0.22um membrane filtrations of Suo Malu peptides are taken, it is standby to collect filtrate；Filtrate is taken, using inverted polymer chromatograph packing material as stationary phase；Detection wavelength is that 230nm carries out HPLC linear gradient elutions； Mobile phase A is：0.5% acetic acid, ammoniacal liquor adjust the aqueous solution of pH=7.6, and Mobile phase B is：Pure acetonitrile；Gradient Initial Gradient B phases 5% keeps 5min, then 60min to 45%；Collect the cut containing Suo Malu peptides；With rotary evaporator water bath temperature at 30 ~ 35 DEG C, vacuum removes partial acetonitrile below -0.09MPa；Obtain Suo Malu Purification solution of peptide；Purification solution of Suo Malu peptides is taken, using eight alkyl silane bonded silica gels as stationary phase；Detection wavelength is carried out for 230nm HPLC linear elutions；0.2% trifluoracetic acid, it is A phases that triethylamine, which adjusts the aqueous solution of pH=2.5, contains 0.1% trifluoroacetic acetonitrile Solution is B phases；Gradient Initial Gradient B phases 5% keep 5min, and then 60min to 55%, collects evaporating containing Suo Malu peptides Point；With rotary evaporator water bath temperature at 30 ~ 35 DEG C, vacuum removes partial acetonitrile below -0.09MPa；Obtain Suo Malu Peptide purification solution.
- 3. the method for purifying Suo Malu peptides according to claim 2, it is characterised in that rotary evaporator water bath temperature is 30 ~35℃。
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108640985A (en) * | 2018-06-25 | 2018-10-12 | 杭州诺泰澳赛诺医药技术开发有限公司 | A method of purifying Suo Malu peptides |
| CN108794618A (en) * | 2018-06-25 | 2018-11-13 | 杭州诺泰澳赛诺医药技术开发有限公司 | A method of purifying Liraglutide |
| CN109354622A (en) * | 2018-12-05 | 2019-02-19 | 苏州汇通色谱分离纯化有限公司 | A kind of Suo Malu peptide purification filler special and its purification process |
| CN109456402A (en) * | 2018-12-31 | 2019-03-12 | 江苏诺泰澳赛诺生物制药股份有限公司 | A kind of synthetic method of Suo Malu peptide |
| CN110845602A (en) * | 2019-11-29 | 2020-02-28 | 苏州天马医药集团天吉生物制药有限公司 | Method for separating and purifying somaglutide |
| WO2020190757A1 (en) * | 2019-03-15 | 2020-09-24 | Novetide Ltd. | Improved processes for the preparation of semaglutide |
| CN111848777A (en) * | 2020-08-17 | 2020-10-30 | 深圳瑞德林生物技术有限公司 | Method for purifying somaglutide |
| CN112175068A (en) * | 2020-09-28 | 2021-01-05 | 深圳深创生物药业有限公司 | Method for purifying semaglutide |
| CN112279907A (en) * | 2019-07-27 | 2021-01-29 | 深圳市健元医药科技有限公司 | Purification method of somaglutide |
| CN112940102A (en) * | 2020-12-30 | 2021-06-11 | 苏州天马医药集团天吉生物制药有限公司 | Purification method of Somalutide |
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| CN106928343A (en) * | 2015-12-30 | 2017-07-07 | 深圳翰宇药业股份有限公司 | The preparation method of Suo Malu peptides |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108794618B (en) * | 2018-06-25 | 2021-08-17 | 杭州诺泰澳赛诺医药技术开发有限公司 | Method for purifying liraglutide |
| CN108794618A (en) * | 2018-06-25 | 2018-11-13 | 杭州诺泰澳赛诺医药技术开发有限公司 | A method of purifying Liraglutide |
| CN108640985A (en) * | 2018-06-25 | 2018-10-12 | 杭州诺泰澳赛诺医药技术开发有限公司 | A method of purifying Suo Malu peptides |
| CN109354622A (en) * | 2018-12-05 | 2019-02-19 | 苏州汇通色谱分离纯化有限公司 | A kind of Suo Malu peptide purification filler special and its purification process |
| CN109456402A (en) * | 2018-12-31 | 2019-03-12 | 江苏诺泰澳赛诺生物制药股份有限公司 | A kind of synthetic method of Suo Malu peptide |
| WO2020190757A1 (en) * | 2019-03-15 | 2020-09-24 | Novetide Ltd. | Improved processes for the preparation of semaglutide |
| CN112279907B (en) * | 2019-07-27 | 2023-10-03 | 深圳市健元医药科技有限公司 | Purification method of somalupeptide |
| CN112279907A (en) * | 2019-07-27 | 2021-01-29 | 深圳市健元医药科技有限公司 | Purification method of somaglutide |
| CN110845602A (en) * | 2019-11-29 | 2020-02-28 | 苏州天马医药集团天吉生物制药有限公司 | Method for separating and purifying somaglutide |
| CN111848777A (en) * | 2020-08-17 | 2020-10-30 | 深圳瑞德林生物技术有限公司 | Method for purifying somaglutide |
| CN112175068B (en) * | 2020-09-28 | 2021-06-25 | 深圳深创生物药业有限公司 | Method for purifying semaglutide |
| CN112175068A (en) * | 2020-09-28 | 2021-01-05 | 深圳深创生物药业有限公司 | Method for purifying semaglutide |
| CN112940102A (en) * | 2020-12-30 | 2021-06-11 | 苏州天马医药集团天吉生物制药有限公司 | Purification method of Somalutide |
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Application publication date: 20180410 |