CN102381919A - Grouping preparation method of amino acid groups with alkaline, acid and neutral functions - Google Patents
Grouping preparation method of amino acid groups with alkaline, acid and neutral functions Download PDFInfo
- Publication number
- CN102381919A CN102381919A CN2010102718085A CN201010271808A CN102381919A CN 102381919 A CN102381919 A CN 102381919A CN 2010102718085 A CN2010102718085 A CN 2010102718085A CN 201010271808 A CN201010271808 A CN 201010271808A CN 102381919 A CN102381919 A CN 102381919A
- Authority
- CN
- China
- Prior art keywords
- amino acid
- acidic
- neutral
- acidic amino
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Images
Abstract
The invention relates to a grouping preparation method of amino acid groups with alkaline, acid and neutral functions. The grouping preparation method comprises steps that 1, hydrolysis of protein is realized to obtain amino acid mixture liquor, 2, the pH (potential of hydrogen) value of the mixture liquor is regulated so that the alkali amino acid is provided with positive charges, and the alkali amino acid is separated by the aid of cation exchanging resin, 3, the pH value of mixture liquor which is separated from the alkali amino acid is regulated so that all acidic amino acid is provided with negative charges, and the acidic amino acid is separated by the aid of anion exchanging resin, and 4, separated mixture liquor is dried to obtain neutral amino acid powder. The acidic amino acid, the neutral amino acid and the alkali amino acid in a hydrolysis product of the protein are successfully separated by means of ion exchanging steps with certain sequence, the grouping preparation method is simple in process and low in cost, and the three amino acid groups display different chemical and physical properties as analysis results show, and can be used as functional materials in texture or biomedical application.
Description
Technical field
The present invention relates generally to a kind of technology that function amino acid in the protein hydrolyzate is divided into groups to prepare; Relating in particular to proteolysis is become amino-acid compound, is three groups with these compound separation then, promptly acid, neutral and alkaline function amino acid group.
Background technology
Protein is linked together through peptide bond by many amino acid and forms.Proteinic hydrolysis takes place when peptide bond destroys.Proteinic hydrolysate is that protein is hydrolyzed or resolves into its each amino acid composition.
The method that many protein hydrolysates are arranged; The most frequently used is in strong acid or highly basic, to boil for a long time, perhaps promotes abiogenous hydrolytic process with enzyme.Existing patent how to have told about respectively under alkaline condition with acidic conditions under X 1000.Patent has been told about and how have been selected for use enzyme to come X 1000 in addition.
Prior art also discloses the method for many separation and purifying amino-acid compound.For example, existing patent is separated monamino acid or basic aminoacids through the Zeo-karb tower from protein hydrolysate; Other has patent to provide a kind of purifying amino acid whose method, comprises the amino acid solution that contains impurity is contacted with ion exchange resin optionally amino acid is adsorbed onto on the resin; Other has patent to relate to the amino acid whose technology of a kind of purifying, especially a kind of through electrodialysis with the amino acid separation processes; Other has patent to tell about a kind of method of amino acid separation, especially comes amino acid separation from protein hydrolysate through in acetone soln, decomposing amino-acid compound; Other has patent to tell about the technology that selected amino acid is separated from mixture, and this mixture contains different compounds and the polymer materials that comprises the selected amino acid molecular marking; Other has patent to tell about use chirality eluent through the liquid phase chromatography amino acid separation; Other have patent provide a kind of from impurity the method for amino acid separation and salt thereof, this impurity contain comprise amine and acid the non-basically extraction agent that dissolves each other mutually; Other has patent to tell about the technology of coming amino acid separation from the aqueous solution with the adsorption of different sorts zeolite; Other has patent to tell about a kind of being used for from the method for the aqueous solution separating at least one die aromatischen Aminosaeuren of kilnitamin and strongly-acid gel Zeo-karb.
For these amino-acid compounds in the protein hydrolyzate, they can be divided into acidic amino acid, basic aminoacids with too much amino group (NH2) and the neutral amino acids with equivalent COOH and NH2 with too much carboxylic group (COOH) respectively.Though have many about preparation protein hydrolyzate and the amino acid whose technology of separation/purification; But also there is not prior art to claim that a kind of method of exploitation can be divided into the amino-acid compound in the protein hydrolyzate three groups, i.e. acidity, neutrality and basic aminoacids.
Summary of the invention
The technical problem that the present invention will solve is; Do not relate to the defective that amino-acid compound is divided into acidity, neutrality and basic aminoacids in the technology to existing amino acid separation; Provide a kind of proteolysis is become amino-acid compound, and function amino acid wherein is divided into the method for acidity, neutrality and alkaline three major types function amino acid group.
The technical solution adopted for the present invention to solve the technical problems is: construct a kind of method that mixed amino acid solution is divided into groups to prepare according to acidity, neutrality and alkaline three major types function amino acid; Ion exchange process through particular order can successfully separate acid, neutral from the blended protein degradation products and these three groups of amino acid of alkalescence, and through dry its corresponding dry powder of collecting.
The invention provides a kind of method of dividing into groups to prepare alkalescence, acidity and neutral function amino acid group, mainly may further comprise the steps:
1) protein is hydrolyzed and filters the mixing solutions that the back obtains to contain multiple amino acids;
The pH value of 2) regulating said amino acid mixing solution is lower than the iso-electric point of all basic aminoacidss in this mixing solutions and is higher than the iso-electric point of all neutral amino acidss; The lotus so that all basic aminoacidss become positively charged; Use Zeo-karb to separate basic aminoacids subsequently, and with basic aminoacids wash-out and the dry basic aminoacids powder that obtains from the Zeo-karb;
3) regulating step 2) in separated parlkaline amino group of amino acids acid mixing solutions the pH value be lower than the iso-electric point of all neutral amino acidss in this mixing solutions and be higher than the iso-electric point of all acidic amino acids; So that negative charge on all acidic amino acid bands; Use anionite-exchange resin to separate acidic amino acid subsequently, and with acidic amino acid wash-out and the dry acidic amino acid powder that obtains from the anionite-exchange resin;
4) the amino acid mixing solution that has separated parlkaline amino acid and acidic amino acid in the step 3) is carried out drying and obtain the neutral amino acids powder.
The grouping of embodiment of the present invention prepares the method for alkalescence, acidity and neutral function amino acid group; Have following beneficial effect: the present invention is through being hydrolyzed to protein; And further adopt the ion-exchange step of particular order to carry out successfully separating with these three groups of amino acid of alkalescence to acid, neutral; Its technology is simple, and cost is low; And analytical results show isolating three groups of amino acid show different separately chemistry and physical properties, can be used as the weaving or biomedical applications in functional materials.
Description of drawings
Below in conjunction with accompanying drawing and embodiment the present invention is described further, in the accompanying drawing:
Fig. 1 is the method flow diagram that divides into groups to prepare alkalescence, acidity and neutral function amino acid group in the preferred embodiment of the present invention;
Fig. 2 (a), Fig. 2 (b) and Fig. 2 (c) are respectively the scanning electron microscope image of alkalescence, neutrality and acidic amino acid powder;
Fig. 3 (a), Fig. 3 (b), Fig. 3 (c) and Fig. 3 (d) are respectively the thermogravimetric-differential scanning calorimetric curve of wool, alkalescence, neutrality and acidic amino acid;
Fig. 4 is the Fourier transform infrared spectroscopy figure of wool, l-arginine, alkalescence, neutrality and acidic amino acid;
Fig. 5 is the X-ray powder diffraction figure of wool, alkalescence, acidity and neutral amino acids.
Embodiment
In order to make the object of the invention, technical scheme and advantage clearer,, the present invention is further elaborated below in conjunction with accompanying drawing and embodiment.
See also Fig. 1, be the method flow diagram of divide into groups in the preferred embodiment of the present invention preparation alkalescence, acidity and neutral function amino acid group.As shown in Figure 1, grouping provided by the invention prepares the method for alkalescence, acidity and neutral function amino acid group, mainly may further comprise the steps:
1), perhaps use enzyme to promote abiogenous hydrolytic process that protein source is hydrolyzed into aminoacid mixture solution through in strong acid or highly basic, boiling for a long time; Filter hydrolysising product solution so that carry out subsequent disposal, obtained containing the mixing solutions of acidity, neutrality and basic aminoacids.
2) separate basic aminoacids through Zeo-karb.The pH value of the amino acid mixing solution after at first will filtering is adjusted to iso-electric point (the isoelectric point that is lower than all basic aminoacidss in this mixing solutions; PI) but be higher than the iso-electric point of all neutral amino acidss; I.e. 5.05＜pH＜7.60; Better between 6.0 to 7.0, so that have only the basic aminoacids lotus that becomes positively charged.Subsequently competent Zeo-karb (is included but not limited to H
+Or Na
+The type Zeo-karb) puts into amino acid mixing solution after the above-mentioned adjusting pH value; React the enough time; 24 hours better, exchanges on the resin, afterwards as much as possible so that will have the basic aminoacids of positive charge; The resin that obtains is separated from amino acid mixing solution, and with the residual solution of zero(ppm) water flush away resin surface.For with basic aminoacids wash-out from the resin; Resin is immersed in the basic soln (for example NaOH solution) of pH greater than all basic aminoacids iso-electric points; Be pH＞10.76, better between 11.0 to 12.0, so that therefore negative charge also separates from resin on the basic aminoacids band.Afterwards through the elutriant that contains basic aminoacids being carried out spraying drying or lyophilize to collect the basic aminoacids powder.
3) separate acidic amino acid through anionite-exchange resin.Above-mentioned pH value of having separated parlkaline amino group of amino acids acid mixing solutions is adjusted to the iso-electric point that is lower than all neutral amino acidss in this mixing solutions but the iso-electric point that is higher than all acidic amino acids; I.e. 3.15＜pH＜5.05; Better between 4.0 to 5.0, so that have only negative charge on the acidic amino acid band.Subsequently competent anionite-exchange resin (is included but not limited to OH
-Or Cl
-Type anionite-exchange resin) put into amino acid mixing solution after this adjusting pH value; React the enough time; 24 hours better; Exchange to as much as possible on the resin so that will have the acidic amino acid of negative charge, afterwards the resin that obtains is separated from mixing solutions, and with the residual solution of zero(ppm) water flush away resin surface.For with acidic amino acid wash-out from the resin; Resin is immersed in the acidic solution (like HCl solution) of pH value less than all acidic amino acid iso-electric points; Be pH＜2.85, better between 1.0 to 2.0, therefore lotus also separates from resin so that acidic amino acid becomes positively charged.Afterwards through the elutriant that contains acidic amino acid being carried out spraying drying or lyophilize to collect the acidic amino acid powder.
4) separate neutral amino acids.Collect the neutral amino acids powder through the mixing solutions that separates parlkaline and acidic amino acid being carried out spraying drying, lyophilize or other drying mode.
The result show the present invention isolating three groups of amino acid show different chemistry and physical properties, can be used as the weaving or biomedical applications in functional materials.
Following Example will further specify invention, but be not limited to the present invention.
1) the 100g wool is put into 1.0L 1.5molL
-1Sodium hydroxide solution in, then in 120 ℃ HP steam well heater the reaction 24 hours so that wool is hydrolyzed to amino acid.Amino acid whose amount is measured with ninhydrin reaction, and the amount that contains the composition of peptide bond is measured with biuret reaction, and the result confirms that wool nearly all is hydrolyzed to amino acid.Subsequently, the amino acid mixing solution with gained hydrolysis gained filters so that carry out subsequent disposal.
2) the pH value with the amino acid mixing solution that filters is adjusted to 7.0, so that basic aminoacids becomes positively charged, then with competent H
+The type Zeo-karb was put into amino acid mixing solution reaction 24 hours, exchanged on the resin with the basic aminoacids that will have positive charge, afterwards, the resin that obtains is separated from solution, and with the residual solution of zero(ppm) water flush away resin surface.For with amino acid wash-out from the resin, resin is immersed in the NaOH solution of pH=12.0, so that negative charge and therefore separating from resin on the basic aminoacids band carries out further spray drying treatment to obtain the basic aminoacids powder with gained solution.
3) from amino acid mixing solution, separate after the basic aminoacids, the pH value of remaining mixing solutions is adjusted to 5.0, so that negative electricity on the acidic amino acid band, with competent OH
-Type anionite-exchange resin was put into solution reaction 24 hours, exchanged on the resin with the acidic amino acid that will have negative charge, afterwards, the resin that obtains is separated from solution, and with the residual solution of zero(ppm) water flush away resin surface.For with amino acid wash-out from the resin, resin is immersed in the HCl solution of pH=2.0, so that acidic amino acid becomes positively charged and therefore separate from resin, gained solution is carried out further spray drying treatment to obtain the acidic amino acid powder.
4) from amino acid mixing solution, separate after alkalescence and the acidic amino acid, remaining mixing solutions is carried out spraying drying to obtain the neutral amino acids powder.
Be respectively ESEM (scanning electron microscope, the SEM) image of alkalescence, neutrality and acidic amino acid powder shown in Fig. 2 (a), Fig. 2 (b) and Fig. 2 (c).Obviously, the surface topography of these powder of amino acids is very different, and basic aminoacids is stiffened and crisp more, and acidic amino acid is then softer and have viscosity, what is interesting is that neutral amino acids seems between alkalescence and acidic amino acid.This possibly can confirm through further sign owing to these several groups amino acid whose different propertiess cause.
In order to explain the difference of several groups of powder of amino acids surface topographies, we attempt investigating through the thermogravimetric-differential scanning calorimetric curve of measure sample some physical propertiess of powder of amino acids.Thermogravimetric (Thermogravimetry; TG) method of masurement is an a kind of good method of measuring the component content with different phase transition temperatures and temperature of fusion; (differential scanning calorimetry DSC) is a kind of be used for measuring the temperature that mixture phase transition process comprised and instrument of energy variation to DSC.
Be respectively the TG-DSC curve of wool, alkalescence, neutrality and acidic amino acid shown in Fig. 3 (a), Fig. 3 (b), Fig. 3 (c) and Fig. 3 (d); Their corresponding second-order transition temperatures, decomposition temperature and quality change (400 ℃) are listed in the table 1.From the result, can find; Basic aminoacids has higher second-order transition temperature (73.8 ℃), decomposition temperature (305.3 ℃) and lower quality change (17.40%); And acidic amino acid has lower second-order transition temperature (54.6 ℃), decomposition temperature (158.9 ℃) and higher quality change (39.01%); What is interesting is that these character of neutral amino acids have Jie in the intermediary parameter.These results have also supported to characterize viewed phenomenon from surface topography.
Table 1
Shown in Figure 4 be wool, l-arginine, alkalescence, neutrality and acidic amino acid Fourier transform infrared spectroscopy (Fourier transform infrared, FTIR) figure, their corresponding characteristic peaks all are indicated among the figure.After the hydrolysis, the peptide bond in the wool is destroyed, and its characteristic peak disappears.Spectrogram acid and neutral amino acids is not obviously distinguished, and the spectrogram of basic aminoacids is then different, and this is because the effect of l-arginine characteristic peak.
Shown in Figure 5 is X-ray powder diffraction (X-raypowder diffraction, XRPD) figure of wool, alkalescence, acidity and neutral amino acids.The result shows that wool is unbodied before hydrolysis, and after hydrolysis, all amino acid of separating all have the component of crystallized form, and this possibly be because the existence of crystalline aminoacid is arranged.
Above-mentioned experimental result shows that wool successfully is hydrolyzed into amino acid through in sodium hydroxide, boiling, and is further separated into three groups through ion exchange technique, i.e. alkalescence, neutrality and acidic amino acid.These three groups of amino acid whose different propertiess that disclose through sign show that they can be used as Biofunctional materials and are used among the different application.
1) 40g silk is put into 1.0L 2.0molL
-1HCl solution in, then in 120 ℃ HP steam well heater the reaction 24 hours so that silk is hydrolyzed to amino acid.Amino acid whose amount is measured with ninhydrin reaction, and the amount that contains the composition of peptide bond is measured with biuret reaction, and the result confirms that silk nearly all is hydrolyzed to amino acid.Subsequently, the amino acid mixing solution with gained filters so that carry out subsequent disposal.
2) the pH value with the amino acid mixing solution that filters is adjusted to 7.60, so that basic aminoacids becomes positively charged, then with competent Na
+The type Zeo-karb was put into amino acid mixing product solution reaction 24 hours, exchanged on the resin with the basic aminoacids that will have positive charge, afterwards, the resin that obtains is separated from solution, and with the residual solution of zero(ppm) water flush away resin surface.For with amino acid wash-out from the resin; Resin is immersed in the NaOH solution of pH=10.76; So that therefore negative charge also separates from resin on the basic aminoacids band, gained solution is carried out further lyophilize handle to obtain the basic aminoacids powder.
3) from amino acid mixing solution, separate after the basic aminoacids, the pH value of surplus solution is adjusted to 5.05, so that negative charge on the acidic amino acid band, with competent Cl
-Type anionite-exchange resin was put into solution reaction 24 hours, exchanged on the resin with the acidic amino acid that will have negative charge, afterwards, the resin that obtains is separated from solution, and with the residual solution of zero(ppm) water flush away resin surface.For with amino acid wash-out from the resin, resin is immersed in the HCl solution of pH=2.85, the lotus and therefore separating from resin so that acidic amino acid becomes positively charged carries out further lyophilize with gained solution and handles to obtain the acidic amino acid powder.
4) from amino acid mixing solution, separate after alkalescence and the acidic amino acid, remaining mixing solutions is carried out spraying drying to obtain the neutral amino acids powder.
1) 200g pig blood meal is dissolved in the 1000ml zero(ppm) water, adding massfraction according to the weight of pig blood meal is 2% papoid, and mixture reacted 24 hours in 50 ℃ of Water Tanks with Temp.-controlled, being amino acid with proteolysis.Amino acid whose amount is measured with ninhydrin reaction, and the amount that contains the composition of peptide bond is measured with biuret reaction, and the result confirms that the pig blood meal nearly all is hydrolyzed to amino acid.Subsequently, gained amino acid mixing solution is filtered so that carry out subsequent disposal.
2) the pH value with the amino acid mixing solution that filters is adjusted to 5.05, and the lotus so that basic aminoacids becomes positively charged is then with competent Na
+The type Zeo-karb was put into amino acid mixing solution reaction 24 hours, exchanged on the resin with the basic aminoacids that will have positive charge, afterwards, the resin that obtains is separated from solution, and with the residual solution of zero(ppm) water flush away resin surface.For with amino acid wash-out from the resin, resin is immersed in the NaOH solution of pH=12.8, so that negative electricity and therefore separating from resin on the basic aminoacids band carries out further spray drying treatment to obtain the basic aminoacids powder with gained solution.
3) from amino acid mixing solution, separate after the basic aminoacids, the pH value of surplus solution is adjusted to 3.15, so that negative charge on the acidic amino acid band, with competent OH
-Type anionite-exchange resin was put into solution reaction 24 hours, exchanged on the resin with the acidic amino acid that will have negative charge, afterwards, the resin that obtains is separated from solution, and with the residual solution of zero(ppm) water flush away resin surface.For with amino acid wash-out from the resin, resin is immersed in the HCl solution of pH=1.5, the lotus and therefore separating from resin so that acidic amino acid becomes positively charged carries out further spray drying treatment to obtain the acidic amino acid powder with gained solution.
4) from amino acid mixing solution, separate after alkalescence and the acidic amino acid, remaining mixing solutions is carried out spraying drying to obtain the neutral amino acids powder.
Claims (11)
1. a method of dividing into groups to prepare alkalescence, acidity and neutral function amino acid group is characterized in that, may further comprise the steps:
1) protein is hydrolyzed and filters the mixing solutions that the back obtains to contain multiple amino acids;
The pH value of 2) regulating said amino acid mixing solution is lower than the iso-electric point of all basic aminoacidss in this mixing solutions and is higher than the iso-electric point of all neutral amino acidss; The lotus so that all basic aminoacidss become positively charged; Use Zeo-karb to separate basic aminoacids subsequently, and with basic aminoacids wash-out and the dry basic aminoacids powder that obtains from the Zeo-karb;
3) regulating step 2) in separated parlkaline amino group of amino acids acid mixing solutions the pH value be lower than the iso-electric point of all neutral amino acidss in this mixing solutions and be higher than the iso-electric point of all acidic amino acids; So that negative charge on all acidic amino acid bands; Use anionite-exchange resin to separate acidic amino acid subsequently, and with acidic amino acid wash-out and the dry acidic amino acid powder that obtains from the anionite-exchange resin;
4) the amino acid mixing solution that has separated parlkaline amino acid and acidic amino acid in the step 3) is carried out drying and obtain the neutral amino acids powder.
2. method according to claim 1 is characterized in that, through in strong acid or highly basic, boiling for a long time protein is hydrolyzed in the said step 1); Perhaps use enzyme to quicken abiogenous hydrolytic process.
3. method according to claim 1 is characterized in that, said step 2) in regulate said amino acid mixing solution the pH value between 5.05～7.60.
4. method according to claim 1 is characterized in that, the pH value that adjusting has separated parlkaline amino group of amino acids acid mixing solutions in the said step 3) is between 3.15～5.05.
5. method according to claim 1 is characterized in that, said step 2) in use the pH value greater than the basic soln of all basic aminoacids iso-electric points with said basic aminoacids wash-out from the Zeo-karb.
6. method according to claim 5 is characterized in that, said step 2) in use the pH value greater than 10.76 sodium hydroxide solution with said basic aminoacids wash-out from the Zeo-karb.
7. method according to claim 1 is characterized in that, use in the said step 3) pH value less than the acidic solution of all acidic amino acid iso-electric points with said acidic amino acid wash-out from the anionite-exchange resin.
8. method according to claim 7 is characterized in that, use in the said step 3) pH value less than 2.85 hydrochloric acid soln with said acidic amino acid wash-out from the anionite-exchange resin.
9. according to any described method in the claim 1 to 8, it is characterized in that said Zeo-karb comprises: H
+Or Na
+The type Zeo-karb.
10. according to any described method in the claim 1 to 8, it is characterized in that said anionite-exchange resin comprises: OH
-Or Cl
-Type anionite-exchange resin.
11., it is characterized in that said drying comprises spraying drying or lyophilize with the technology that obtains basic aminoacids powder, acidic amino acid powder or neutral amino acids powder according to any described method in the claim 1 to 8.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102718085A CN102381919A (en) | 2010-09-03 | 2010-09-03 | Grouping preparation method of amino acid groups with alkaline, acid and neutral functions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102718085A CN102381919A (en) | 2010-09-03 | 2010-09-03 | Grouping preparation method of amino acid groups with alkaline, acid and neutral functions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102381919A true CN102381919A (en) | 2012-03-21 |
Family
ID=45821816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010102718085A Pending CN102381919A (en) | 2010-09-03 | 2010-09-03 | Grouping preparation method of amino acid groups with alkaline, acid and neutral functions |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102381919A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102618610A (en) * | 2012-03-26 | 2012-08-01 | 苏州大学 | Preparation method of sericin compound amino acid |
| CN103145573A (en) * | 2013-03-27 | 2013-06-12 | 中粮生物化学（安徽）股份有限公司 | Purification method of lysine |
| CN106748871A (en) * | 2016-11-29 | 2017-05-31 | 岳阳科罗德联合化学工业有限公司 | A kind of green circulatory industrial production process of amino acid surfactant |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1734033A1 (en) * | 2004-04-07 | 2006-12-20 | Asahi Kasei Chemicals Corporation | Method of purifying amino acid |
| CN101479292A (en) * | 2006-06-28 | 2009-07-08 | 协和发酵生化株式会社 | Method for purification of oligopeptide |
-
2010
- 2010-09-03 CN CN2010102718085A patent/CN102381919A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1734033A1 (en) * | 2004-04-07 | 2006-12-20 | Asahi Kasei Chemicals Corporation | Method of purifying amino acid |
| CN101479292A (en) * | 2006-06-28 | 2009-07-08 | 协和发酵生化株式会社 | Method for purification of oligopeptide |
Non-Patent Citations (2)
| Title |
|---|
| 周骏山: "《实用氨基酸手册》", 31 December 1989, 无锡市氨基酸研究所科技情报室 * |
| 王镜岩等: "《生物化学》", 30 September 2002, 高等教育出版社 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102618610A (en) * | 2012-03-26 | 2012-08-01 | 苏州大学 | Preparation method of sericin compound amino acid |
| CN103145573A (en) * | 2013-03-27 | 2013-06-12 | 中粮生物化学（安徽）股份有限公司 | Purification method of lysine |
| CN106748871A (en) * | 2016-11-29 | 2017-05-31 | 岳阳科罗德联合化学工业有限公司 | A kind of green circulatory industrial production process of amino acid surfactant |
| CN106748871B (en) * | 2016-11-29 | 2019-03-05 | 岳阳科罗德联合化学工业有限公司 | A kind of green circulatory industrial production process of amino acid surfactant |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7311836B2 (en) | Process for producing amino acid or salt thereof by column technique and production apparatus thereof | |
| CN102381919A (en) | Grouping preparation method of amino acid groups with alkaline, acid and neutral functions | |
| CN103664665A (en) | Solid sodium sarcosine preparation method | |
| CN108484665A (en) | A method of the separation and Extraction L-glufosinate-ammonium from enzymatic conversion liquid | |
| WO2014002674A1 (en) | Method for producing lignin from biomass using lignin-dissolving ionic liquid, and method for producing lignin, hemicellulose and cellulose | |
| CN109942447A (en) | A kind of amino acid-extraction | |
| JPS5931520B2 (en) | Method for producing silk fibroin peptide aqueous solution | |
| JP2508554B2 (en) | Method for producing surface modification component solution and method for producing adsorbent | |
| CN1164565C (en) | Process for preparing amino acids from natural albumen | |
| TWI243822B (en) | Improved process for preparing N-phosphonomethyl iminodiacetic acid | |
| CN101838211B (en) | Processing method for producing intermediate 2-aminobutyric acid of levetiracetam | |
| CN103214113A (en) | Chromatographic separation method of sodium chloride and sodium glycollate in waste water in production process of sodium carboxy methyl cellulose | |
| JP3546592B2 (en) | Phytic acid purification method | |
| CN104693054A (en) | L-amino acid sulfate type chiral ionic liquid and preparation method thereof | |
| JPH0393757A (en) | Production of alpha-amino acid | |
| JPH024534B2 (en) | ||
| AU678824B2 (en) | Resin regeneration process | |
| US2533215A (en) | Process for the manufacture of arginine base | |
| EP4015639A1 (en) | Means and methods for manufacturing racemic alanine for the mgda synthesis | |
| DE2410850C3 (en) | Process for the production of peptides | |
| JPS6013758A (en) | Purification of tryptophan | |
| JPS604155A (en) | Separation of l-leucine and l-isoleucine | |
| CN106117543A (en) | The post-processing approach of PEKK crude product | |
| CN117509720A (en) | Method for preparing high-purity titanium dioxide by self-generated seed crystal nucleation method | |
| JPH0780822B2 (en) | Method for separating and purifying amino acids |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20120321 |