CN104163767B - Method for purifying amino acids and polypeptide water-soluble substances - Google Patents
Method for purifying amino acids and polypeptide water-soluble substances Download PDFInfo
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Abstract
The invention discloses a method for purifying amino acids and polypeptide water-soluble substances and belongs to the technical field of protein and polypeptide purification. The method comprises the following steps of adjusting a pH value of an amino acid or/and polypeptide crude product aqueous solution to an appropriate value so that impurities having solubility similar to that of the desired amino acid or/and polypeptide in the follow-up organic solvent precipitation method are transformed into products having solubility different from that of the desired amino acid or/and polypeptide, adding an acid into the solution to adjust the pH value and then carrying out organic solvent precipitation so that a fined product is obtained and salt removal and product purification are realized. The method provides a simple and effective separation purification method, avoids the influence produced by difficultly-removed salts such as ammonium salt on product purity and physical properties in synthesis, saves a cost, has a small solvent treating capacity and small environmental pollution, has simple processes and a low production cost and is especially suitable for large-scale industrial production.
Description
Technical field
The invention belongs to protein and polypeptide purification techniques field are and in particular to a kind of amino acid and polypeptide water-soluble substances
Purification process, particularly to a kind of for process containing and/or the amino acid of villaumite or/and the purification process of polypeptide crude product.
Background technology
Developing rapidly with amino acid and polypeptide drugs market in recent years, its prospect shows heartening scene,
Its preparation and production technology also get more and more, and the research and development of peptide separation purification technique is also increasingly subject to the concern of expert,
Some new technologies and new technology are employed, and promote the research and development of biologically active polypeptide to become a focus of scientific and technological circle.But
Be general Peptide systhesis the polypeptide first product concentration that obtains of technique relatively low, impurity is complicated, the especially physicochemical property of impurity and mesh
Mark polypeptide is quite similar, thus isolates and purifies relatively difficult.Conventional separating and purifying technology, such as general solvent deposition, tie again
Crystalline substance, the technical operating procedure such as extraction is complicated, and the time is long, easy in inactivation, and consumption raw material is many, and the rate of recovery is low, although both at home and abroad in polypeptide
Research on take substantial amounts of time and efforts, delivered hundreds of research paper, the separating and purifying technology of polypeptide still enters
Postpone slow.
Chinese patent cn201080040450.3 discloses a kind of many based on fast protein liquid chromatography (fplc) purifying
The method of peptide, comprises the following steps: a) applies the solution comprising described polypeptide to the chromatographic apparatus comprising fixing phase；B) lead to
Cross the fixing phase making described solution through described chromatographic apparatus, described polypeptide is divided with the other being contained in described liquid solution
Son separates；C) reclaim polypeptide from chromatographic apparatus to flow through thing or eluate；And d) by filter by way of to comprise reclaim
Polypeptide flow through thing or eluate is sterilized.But the method solvent treating capacity is big, and product yield is low, cumbersome, industrialization
Production need to improve further.
Chinese patent cn201210214758.6 disclose a kind of method of purified polypeptide it is characterised in that by be obtained
After the pretreatment of polypeptide crude product, with octadecylsilane chemically bonded silica as fixing phase, with the concentration perchloric acid that is 0.1～0.8% and dense
Spend and mixed solution is obtained for 0.01～0.08% aqueous sulfuric acid, adjust the ph value of described mixed solution for after 2.0～3.5 with alkali
As a phase, with acetonitrile for b phase, eluted according to the gradient that b phase is 10%～40%, second crude product is obtained；Take described second thick
Product, turn salt using ion-exchange, obtain final product target product.But it is big that the method is also faced with eluting solvent amount, single treatment sample
Amount is little, and wastewater treatment capacity is big, high cost, and industrialized production need to improve further.
Gel chromatography is one of method according to molecular size separation protein mixture, mixture with mobile phase flow through equipped with
During the chromatographic column of gel fixing phase, because the molecular size of material each in mixture is different with shape, therefore, washing post process
In, the maximum material of molecular weight can not enter gel mesh and flow out at first outside post along the space between gel particle；Molecular weight is
Little material is blocked because entering gel mesh, flow velocity slow so as to finally flow out outside post, whole process and filter class
Seemingly, thus also known as gel filtration.Different molecular weight gel are selected to can be used for desalination displacement buffer solution and utilize molecular weight difference
Deng removing thermal source.But post need to be washed with substantial amounts of distilled water or other weak solution, quantity of solvent is big, and wastewater treatment capacity is big, and industrialization should
With there being own situation to be combined to consider.
Displacement analysis is a kind of nonlinear chromatographic technique, has clear advantage compared with traditional elution chromatography technology,
I.e. high applied sample amount high yield high-resolution, being separated sample has concentration effect in separation process, and this technology is increasingly
Cause the concern of people, using a kind of non-linear chromatography technology, by the sample on small molecule displacement agent exchange chromatography post,
Thus it has the characteristic of the less composition of separation component content to reach detached purpose, research shows, the average molecular of displacer
Quality is lower, easier in being combined with fixing phase, therefore separate relative molecular mass less polypeptide when, need less putting
Change agent and could be replaced and be purified, treating capacity also increases therewith.With the development of biotechnological industries, biological substance layer
Analyse detached industrial applications and just seem more and more important.Conventional preparative isolation technics is often by the line in laboratory
Property analytic type isolation technics be simply enlarged, but the restriction of applied sample amount, the dilution effect of low concentration wash-out and chromatography process,
Make that the rate of recovery of sample component is very low, economic benefit is relatively low.
Ion-exchange chromatography (iexc) the technology mainly powered property according to material is different with powered quantity and carry out layer
A kind of isolation technics of analysis. due to this technology high resolution, fractional dose is big, resistance to acids and bases good it is easy to operate, become
A kind of important method for isolated polypeptide. but ph, temperature, molecular size range, ionic strength and salinity are to isolated polypeptide
Impact larger, and different polypeptide is extracted, selected ion-exchanger is different, environmental condition and elution requirement are not yet
Identical, once condition selection is improper, isolating and purifying effect will be very poor. therefore, for not homopolypeptide, its most suitable ion exchange
Agent and corresponding optimum condition improve constantly the important subject that extraction effect is still researcher.
Compared with chromatography of ions and mesolow chromatogram, RPLC (rp-hplc) is with liquid for stream
The chromatographic technique of dynamic phase, has high sensitivity high-voltage high-speed, and pillar can be with Reusability, and separating effect is preferably, more stable,
It is convenient to reclaim, and is particularly well-suited to molecular weight and is less than 5000, the isolating and purifying of especially less than 10000 polypeptide. but because peptide exists
Diffusion coefficient in solution is little, and viscosity ratio is larger, the ph value of medium, ambient temperature, and organic solvent property etc. can lead to some knots
Structure changes, and produces denaturation.This separating and purifying technology there is also other inferior positions, such as: pillar is required strict, need to grope
Good condition etc..Other chromatographic processes, such as hydrophobic interaction chromatography (hic), metal ion affinity chromatography (imac) also has some classes
Like problem.
Ultrafiltration, because membrane separation and purification technology can protect the activity of polypeptide, simple to operate it is not necessary to large-scale instrument, obtain
Extensively apply.Ultrafiltration is exactly the selectivity using film, applies certain pressure, forms pressure differential as driving in the both sides of film
Power, realizes the separation of material by components various in solution through the difference of film migration rate.This technical costs is cheap, no
Any chemical reagent need to be increased, experiment condition is gentle, there is no the change of phase compared with evaporative freezing drying, and do not cause temperature ph
Change, thus deactivation and the self-dissolving of large biological molecule can be prevented.But in ultra-filtration process, because filter membrane surface is easy
Adsorbed material blocking, leads to ultrafiltration efficiency to reduce, the molecular weight of retention material also less and less therefore, in ultra-filtration process
In, select suitable membrane material particularly important.Similar approach, nanofiltration is a kind of separation between counter-infiltration and ultrafiltration
Method, the pore diameter range of NF membrane in several ran, than ultrafiltration effect more preferably, bacterium colloid iron rust can be completely removed
, there is not pollution problem in heavy metal etc., some polypeptides have thermal sensitivity, is heated easily by broken ring, and using traditional purification side
Method is difficult to remove the salinity of low-molecular-weight, thus affecting the purity of product, but is good selection using nanofiltration separation, not only
Organic pollution therein and salinity can also be removed, greatly improve the quality of product by energy reducing energy consumption.
Organic solvent precipitation method is one of conventional method, and its principle is: organic solvent miscible with water (as methyl alcohol,
Ethanol) some amino acid and polypeptide solubility in water can be made to significantly reduce；And it is strong in uniform temperature, ph value and ion
Under degree, the concentration of organic solvent is different, and material precipitation order is also different, therefore, controls the concentration of organic solvent can separate
Purify amino acid and polypeptide.For some and lipid binding than polar side chain in stronger or molecule more, water-fast ammonia
Base acid and polypeptide, can be with organic solvent deposits such as ethanol, acetone and butanol, and they have certain hydrophily and stronger lipophilic
Property, it is preferable extract.Cold separation of ethanol method is extracted immunoglobulin (Ig) and was proposed in 1949 by cohn earliest, for preparing
Gamma globulin.Cold Ethanol Method is also the method that current who code and Products in China code are recommended, not only high resolution,
Refining effect is good, can concurrently separate multiple plasma fractions, and plays the role of antibacterial, virus of removing and go out.But the method is at place
During reason some products, once can not be properly arrived at purification effect, need multiple alcohol analysis, loss is big.Invention describes a letter
Single, the method for practical desalination and purifying, it is particularly suitable for commercial application.
Content of the invention
In real work, it is sometimes difficult to realize amino acid with single method and the separation of polypeptide water soluble compound is pure
Change, a kind of preferable process for separation and purification often requires that the purity of final purpose product and the rate of recovery, and the higher the better, but actual
It is upper that both are difficult to take into account.Accordingly, it is considered to it has between make suitable balance when the condition of separating-purifying and method.
Therefore when needing to purify the product such as amino acid and polypeptide, be according to characteristics such as its physics, chemical property, it is a set of suitable to select
While purification procedures are to obtain highly purified target product, obtain many products as far as possible.The invention is intended to providing a kind of simple
Efficient isolation and purification method, solve the salt of the more difficult removing such as ammonium salt in building-up process to product purity and physical property in terms of
Impact, simultaneously cost-effective, solvent treating capacity is little, and environmental pollution is little, and technological operation is simple, and low production cost is particularly suitable for
Industrialized production.
The main thought of the present invention is the water-soluble amino acids containing ammonium salt etc. or/and polypeptide crude product to be dissolved in water or contains
The mixed solvent of water or directly using solution, plus specific aqueous slkali, such as hydrazine hydrate, lithium hydroxide etc., adjust ph value to 7-
14, preferably 7-11, optimum is 9-10, and the impurity such as ammonium salt are converted into (sinking in organic solvent with target amino acid or/and polypeptide
Separate out in the method for shallow lake) physical property is different, can be dissolved in the suitable industrialized production such as methyl alcohol, ethanol, acetone the hydrazonium salt of organic solvent or
Lithium salts, the solution after conversion can be done or partial concentration with reduced pressure concentration, add water or be not dissolved in water, then acid adding, and example hydrochloric acid etc. is adjusted
Ph value is to any required value (environment of suitable amino acid or/and polypeptide precipitation and ensure that hydrazonium salt or lithium salts are dissolved in follow-up place
The organic solvent of reason), then dropping organic solvent separates out target product at appropriate temperatures, and target product can continue to add
Enter organic solvent to wash at a certain temperature or recrystallize, until obtaining qualified products, product cools down further, suction filtration and baking
Dry etc. obtain highly purified fine work.
Specifically, this purification process is: using having the transforming agent adjusting ph effect by the crude product of amino acid or/and polypeptide
The ph of the aqueous solution is adjusted to fit value (generally 7-14, preferably 7-11, optimum be 9-10), make with target amino acid or/and
Polypeptide similar impurity of dissolubility in follow-up organic solvent precipitation method is converted into the different product of dissolubility, and acid adding adjusts ph value
Afterwards fine work is obtained using organic solvent precipitation method.Wherein, the impurity removing is needed to include ammonium salt and/or villaumite in the above-mentioned methods
Deng they may produce it is also possible to introduce because of acid-base neutralization in ammonolysis；The different product of dissolubility after conversion is permissible
It is dissolved in organic solvent used in follow-up organic solvent precipitation method, including hydrazonium salt or lithium salts etc., the transforming agent of use can include
Hydrazine hydrate or lithium hydroxide etc..
Amino acid in the embodiment of the present invention includes natural and alpha-non-natural amino acid, such as d or l amino acid (the method not shadow
Ring the configuration of object) and their dl mixture；Polypeptide includes the linear peptides or cyclic peptide containing two or more amino acid,
And their derivative, such as ester or acid amides etc..Specific example includes glycine, arginine, water miscible Ganguertai, sweet
Junket dipeptides, glutamine dipeptide etc..
Wherein, the acting as of acid adding: the treatment fluid of organic solvent precipitation method to be employed is adjusted to be suitable for amino acid by acid adding
Or/and the environment of polypeptide precipitation, specifically near target amino acid or/and polypeptide isoelectric point, and take into account hydrazonium salt or lithium salts and having
Dissolubility in machine solvent.
More specifically, this purification process is: using the specific alkali such as hydrazine hydrate or lithium hydroxide, such as 80% hydrazine hydrate, by amino
The ph of the crude product aqueous solution of acid or/and polypeptide is adjusted to 9-10, and the impurity such as ammonium salt and/or villaumite are converted into dissolve in subsequently to be had
The hydrazonium salt of organic solvent or lithium salts used in the machine precipitation method；Concentrate (being such as spin-dried for), with sour (example hydrochloric acid solution), concentrate is adjusted
Save the environment for being suitable for target amino acid or/and polypeptide precipitation, such as near isoelectric point, processed using organic solvent precipitation method and obtain
Object precipitates, and suction filtration is boiled with alcohol reflux, suction filtration, is dried to obtain fine work.
After testing, using the method, yield is more than 80%, notable to the separating effect of the ammonium salt wherein containing, villaumite, and
Do not need to introduce extra solvent, process is simple, and processing cost is low, especially suitable industrialized production.
Specific embodiment
Embodiment one, the refined and desalination of glycine crude product:
1st, take 100g glycine crude product (being obtained by chloracetic acid ammonolysis) in eggplant-shape bottle, plus 50 ml water stirring and dissolving, use
Hydrazine hydrate adjusts ph=10-11.
2nd, 50ml water dissolves are added after being spin-dried for, with hcl tune ph=7 about.After stirring 0.5h, room temperature drips the anhydrous second of 300ml
Alcohol, separates out product.
3rd, the product suction filtration that will separate out, obtains wet product about 100g, adds 800 ml alcohol 600Under c, 0.5h is boiled in backflow.
4th, suction filtration, dries to obtain fine work 88g, yield 88%, chloride ion content is less than 0.1%.
Embodiment two, the refined and desalination of Ganguertai crude product
1st, take 100g Ganguertai crude product (chlorinity 7.2%) in eggplant-shape bottle, plus 60 ml water stirring and dissolving, use 80% water
Close hydrazine and adjust ph=10-11.
2nd, add 60ml water dissolves after being spin-dried for, adjust ph=6 with hcl.After stirring 0.5h, room temperature drips 360ml absolute ethyl alcohol, analysis
Go out product.
3rd, the product suction filtration that will separate out, obtains wet product about 100g, adds 800 ml alcohol 600Under c, 0.5h is boiled in backflow.
4th, suction filtration, dries to obtain fine work 85g, yield 85%, chloride ion content is less than 0.2%.
Embodiment three, the refined and desalination of Ganguertai crude product
1st, take 100g Ganguertai crude product (chlorinity 7.2%) in eggplant-shape bottle, plus 60 ml water stirring and dissolving, use hydroxide
Lithium solution adjusts ph=10-11.
2nd, add 60ml water dissolves after being spin-dried for, adjust ph=6 with hcl.After stirring 0.5h, room temperature drips 360ml absolute ethyl alcohol, analysis
Go out product.
3rd, the product suction filtration that will separate out, obtains wet product about 100g, adds 800 ml alcohol 600Under c, 0.5h is boiled in backflow.
4th, suction filtration, dries to obtain fine work 86g, yield 86%, chloride ion content is less than 0.2%.
Example IV, the refined and desalination of glutamine dipeptide crude product
1st, take 100g glutamine dipeptide crude product (chlorinity 7.2%) in eggplant-shape bottle, plus 50 ml water stirring and dissolving, use 80% water
Close the hydrazine aqueous solution and adjust ph=9-10.
2nd, add 50ml water dissolves after being spin-dried for, adjust ph=7 with hcl.After stirring 0.5h, room temperature drips 300ml absolute ethyl alcohol,
Separate out product.
3rd, the product suction filtration that will separate out, obtains wet product about 100g, adds 800 ml alcohol 600Under c, 0.5h is boiled in backflow.
4th, suction filtration, dries to obtain fine work 82g, yield 82%, chloride ion content is less than 0.2%.
The foregoing is only presently preferred embodiments of the present invention, not in order to limit the present invention, all spirit in the present invention and
Within principle, any modification, equivalent substitution and improvement made etc., should be included within the scope of the present invention.
Claims (4)
1. the purification process of a kind of amino acid and polypeptide water-soluble substances is it is characterised in that incited somebody to action using hydrazine hydrate or lithium hydroxide
The ph of the crude product aqueous solution of amino acid or/and polypeptide is adjusted to 7-11, ammonium salt and/or villaumite are converted into dissolve in subsequently organic
The hydrazonium salt of organic solvent or lithium salts used in the precipitation method；Concentrate, with acid by concentrate be adjusted to be suitable for target amino acid or/and
The environment of polypeptide precipitation, then fine work is obtained using organic solvent precipitation method.
2. purification process according to claim 1 it is characterised in that: described amino acid is water-soluble natural and non-natural ammonia
Base acid.
3. purification process according to claim 1 it is characterised in that: described polypeptide be water miscible Ganguertai, sweet junket
Dipeptides or glutamine dipeptide.
4. purification process according to claim 1 it is characterised in that: ph is adjusted to 9-10.
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| CN110407913A (en) * | 2018-06-11 | 2019-11-05 | 合肥川迪医药技术有限公司 | A kind of process for separation and purification of glutamine dipeptide |
| CN111018572A (en) * | 2019-11-15 | 2020-04-17 | 鞍钢集团矿业有限公司 | Method for preparing fertilizer by desalting amino acid industrial wastewater |
| CN113101360A (en) * | 2021-04-13 | 2021-07-13 | 武汉桀升生物科技有限公司 | Application of low-dose zinc dipeptide in preparation of anti-inflammatory drugs |
| CN115466189B (en) * | 2022-09-19 | 2024-08-30 | 安徽普利药业有限公司 | Purification method of amino acid and derivative thereof |
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| CN101851285A (en) * | 2009-04-03 | 2010-10-06 | 四川省德阳市生化制品有限公司 | Method for preparing sulglycotide |
| US20110020327A1 (en) * | 2008-12-16 | 2011-01-27 | Millipore Corporation | Purification of proteins |
| CN102286069A (en) * | 2011-08-09 | 2011-12-21 | 华南理工大学 | Method for primarily purifying glutathione fermentation liquid by precipitation and separation with organic solvent |
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| JP4522706B2 (en) * | 2002-01-29 | 2010-08-11 | インデナ エッセ ピ ア | Selective extraction, purification and enzymatic modification of soybean β-conglycinin α 'subunit for use as a blood cholesterol lowering agent |
| US20110020327A1 (en) * | 2008-12-16 | 2011-01-27 | Millipore Corporation | Purification of proteins |
| CN101851285A (en) * | 2009-04-03 | 2010-10-06 | 四川省德阳市生化制品有限公司 | Method for preparing sulglycotide |
| CN102286069A (en) * | 2011-08-09 | 2011-12-21 | 华南理工大学 | Method for primarily purifying glutathione fermentation liquid by precipitation and separation with organic solvent |
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Denomination of invention: A purification method for water-soluble substances of amino acids and peptides Granted publication date: 20170118 Pledgee: Bank of Hankou Limited by Share Ltd. Financial Services Center Pledgor: Wuhan jitide Biotechnology Co.,Ltd. Registration number: Y2024980026642 |
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