CN101824443A - Method for removing alanine in reaction system for preparing neutral amino acid - Google Patents
Method for removing alanine in reaction system for preparing neutral amino acid Download PDFInfo
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Abstract
The invention provides a method for removing alanine in a reaction system for preparing neutral amino acid, wherein the reaction system for preparing the neutral amino acid is a reaction system adopting a transaminase method or a fermentation method to prepare the neutral amino acid. The method provided by the invention is as follows: alanine racemase and a catalyst capable of specially catalyzing single chiral amino acid for further reaction are added into the reaction system, thus specially removing the alanine in the reaction system. The method can specially remove the alanine in conversion liquid or fermentation liquid, thus simplifying the separation and purification and refining the technique of the neutral target amino acid.
Description
Technical field
The invention belongs to bioengineering field, specifically, relate to a kind of method of removing the L-Ala in the reaction system for preparing neutral amino acids.
Background technology
Neutral amino acids comprises the non-natural chiral, L-Xie Ansuan, L-Isoleucine and L-leucine etc.Wherein, the non-natural chiral mainly comprises D-amino acid such as L-amino acid such as L-2-aminobutyric acid, L-Terleu, L-norvaline and D-tryptophane, D-leucine, D-Xie Ansuan, D-Terleu.Wherein, the non-natural chiral is except the most of function with natural amino acid, also has the not available premium properties of alpha-non-natural amino acid, has purposes widely at aspects such as medicine synthetic (medicine and agricultural chemicals), food, makeup, particularly have extensive market prospects aspect synthetic, become the fastest chiral drug intermediate of development in recent years at medicine.And L-Xie Ansuan, L-Isoleucine and L-leucine all are indispensable amino acids, because of its special 26S Proteasome Structure and Function, the status of in human life's metabolism, occupying particularly important, therefore has important use, now be mainly used in the preparation mixed amino acid, particularly be applied to high branched-chain amino acid transfusion and oral liquid.
Preparation non-natural L-amino acid and the amino acid whose method of D-have transaminase method etc., and preparation L-Xie Ansuan, L-Isoleucine and the leucic method of L-have fermentation method etc.But when transaminase method and fermentation method prepare above-mentioned neutral amino acids, generation along with above-mentioned neutral amino acids, the capital is accompanied by the generation of L-Ala, particularly when industrial production, than higher, this is to the separation and purification and the refining difficulty greatly of bringing of neutral amino acidss such as L-2-aminobutyric acid, L-Terleu, L-Xie Ansuan, L-norvaline, D-tryptophane, D-Xie Ansuan, D-leucine, D-Terleu with respect to target amino acid content for L-Ala.
But, therefore, adopt conventional chromatography and simple crystallization method to be difficult to remove wherein D-L-Ala or L-L-Ala, and the multistep recrystallization influence purifying and purified yield, increases cost because neutral amino acids is similar with the L-Ala physico-chemical property.Therefore, a kind of method of removing L-Ala is cheaply demanded exploitation urgently.
Summary of the invention
Purpose of the present invention just is, be difficult to remove at L-Ala in the reaction system of the neutral amino acids that has the preparation of transaminase method or fermentation method now, reduce the problem of target amino yield when perhaps removing, a kind of method of removing the L-Ala in the reaction system for preparing neutral amino acids is provided, L-Ala in can specific removal system, and very little for the influence of target amino yield, thus the subsequent purification step can be reduced, reduce the purifying cost.
Removal of the present invention prepares the method for the L-Ala in the reaction system of neutral amino acids, comprise in described reaction system, adding alanine racemase and further catalyst for reaction taking place specificity catalysis single chiral amino acid, by the L-Ala in both described reaction systems of common catalytic elimination.
According to the present invention, further catalyst for reaction takes place and comprises in energy specificity catalysis single chiral amino acid: amino-acid oxidase, amino acid acylase, amino acid aminotransferase, amino acid esterase.
According to the present invention, the alanine racemase of use comprises the alanine racemase that derives from subtilis, Corynebacterium glutamicum, Salmonella typhimurium, intestinal bacteria, Pseudomonas aeruginosa or bacillus stearothermophilus.
According to the present invention; further catalyst for reaction takes place the energy specificity catalysis single chiral amino acid that uses is the enzyme that has optical specificity, can act on L-L-Ala or D-L-Ala, and these enzymes are selected from: amino-acid oxidase, amino acid acylase and amino amino transaminase.
According to a preferred embodiment of the present invention; when the target product of reaction system was L-amino acid, further catalyst for reaction took place and is selected from the energy specificity catalysis single chiral amino acid of use: D-amino-acid oxidase, D-amino acid acylase, D-amino acid transaminase and D-amino acid had specific esterification enzyme.
According to a preferred embodiment of the present invention, the D-amino-acid oxidase that uses is selected from: the D-amino-acid oxidase (pkDAAO) that pig is kidney derived, the D-amino-acid oxidase (TvDAAO) in trigonopsis variabilis source, and the D-amino-acid oxidase (RgDAAO) in rhodotorula source.
According to a preferred embodiment of the present invention, the D-amino acid transaminase that uses is selected from: the D-amino acid transaminase that derives from subtilis, derive from the D-amino acid transaminase of Bacillus sphaericus, and the D-amino acid transaminase that derives from the stearothermophilus ground bacillus.
According to a preferred embodiment of the present invention; when the target product of reaction system was D-amino acid, further catalyst for reaction took place and is selected from the energy specificity catalysis single chiral amino acid of use: L-amino-acid oxidase, L-amino acid acylase, L-amino acid aminotransferase and L-amino acid had specific esterification enzyme.
According to a preferred embodiment of the present invention, the L-amino-acid oxidase of use is selected from: derive from the L-amino-acid oxidase of muddy rhodococcus, derive from and produce sticking mycetozoan L-amino-acid oxidase, and the L-amino-acid oxidase that derives from the snake class.
Use method provided by the invention, can remove the conversion fluid of preparation neutral amino acids or the L-Ala in the fermented liquid specifically, and it is very little for target amino racemization influence, thereby can be under guaranteeing that target amino acid is not by the situation of racemization, simplify target amino separation and purification and process for refining, thereby increase yield.
Embodiment
Below in conjunction with specific embodiment, the invention will be further described.Should be understood that following examples only are used to the present invention is described but not are used to limit scope of the present invention.
In following embodiment of the present invention, amino acid whose analysing and detecting method is with reference to reference (" reverse phase liquid chromatography is measured aminoacids content in the Leaf of Chinese Tallowtree ", Jiangxi agricultural journal: 2007,19 (3), 99-101, Wei Jingguang, Huo Guanghua etc.) in method carry out.
In following embodiment of the present invention, amino acid whose optical activity analysis is with reference to reference (" the multiple amino acids enantiomorph is measured in high performance liquid chromatography and chemometrics method coupling ", Qufu Normal University's journal: 2005.7,31 (3), 86-89, Liu Guangjun) method in is carried out.
In following embodiment of the present invention, at the reaction system of target solution system for adopting conventional transaminase method or fermentation method to prepare neutral amino acids, concrete preparation method can be with reference to Engineering of A Novel Biochemical Pathway for the Biosynthesis of L-2-aminobutyric Acid in Escherichia coli K12, Fotheringham, I.G., Pantaleone, D.P.and Taylor, P.P et.al. (1997) Chim.Oggi 15,33-37; Transaminase biotrans-formation process, Fotheringham, I.G. (2001) US Patent 6197558; With Preparation of d-amino acids by direct fermentative means, Fotheringham, I.G., Taylor, P.P.and Ton, J.L (1998) US Patent 5728555; The Study on Fermentation of L-Xie Ansuan, the biotechnology communication: 2006,17 (3), 381-383, documents such as Liu Xu Qingyang sea of trees Chen Ning.
In following embodiment of the present invention, the alanine racemase that uses is the alanine racemase that derives from subtilis, Corynebacterium glutamicum, Salmonella typhimurium, intestinal bacteria, Pseudomonas aeruginosa or bacillus stearothermophilus, concrete preparation method can be with reference to Preparation of d-amino acids by direct fermentative means, Fotheringham, I.G., Taylor, P.P.and Ton, J.L. (1998) US Patent 5728555; Expression of alr gene from Corynebacterium glutamicum ATCC 13032 in Escherichia coli and molecular characterization of the recombinant alanine racemase.Oikawa, T., A.Tauch, et al. (2006) .Journal of Biotechnology 125 (4): 503-512; Isolation of an Alanine Racemase Gene from Bacillus subtilis and its Use for Plasmid Maintenance in B.subtilis.Ferrari, E., D.J.Henner, et al. (1985) .Bio/Technology 3 (11): 1003-1007.; Cloning of alanine racemase genes from Pseudomonas fluorescens strains and oligomerization states of gene products expressed in Escherichia coli.Ju, J., K.Yokoigawa, et al. (2005) .Journal of Bioscience and Bioengineering 100 (4): 409-417 and/or Thermostable alanine racemase from Bacillus stearothermophilus:molecular cloning of the gene, enzyme purification, and characterization.Inagaki, K., K.Tanizawa, et al. (1986) .Biochemistry 25 (11): 3268-3274. etc.
In following embodiment of the present invention, the D-amino-acid oxidase that uses is the kidney derived D-amino-acid oxidase (pkDAAO) of pig, the D-amino-acid oxidase (RgDAAO) in the D-amino-acid oxidase (TvDAAO) in trigonopsis variabilis source or rhodotorula source, concrete preparation method can be with reference to Genetic and physiological data implicating the new human gene G72 and the gene for d-amino acid oxidase in schizophrenia.Chumakov, I., M.Blumenfeld, et al. (2002) .Proceedings of the National Academy of Sciences 99 (21): 13675-13680; Kinetic mechanism of D-amino acid oxidases from Rhodotorula gracilis and Trigonopsis variabilis.Pollegioni, L., B.Langkau, et al. (1993) .Journal of Biological Chemistry268 (19): 13850-13857 and/or Chinese invention patent CN01132380.9 etc.
In following embodiment of the present invention, the L-amino-acid oxidase that uses is the L-amino-acid oxidase that derives from muddy rhodococcus, derive from and produce sticking mycetozoan L-amino-acid oxidase, and the L-amino-acid oxidase that derives from the snake class, wherein, derive from crotalic L-amino-acid oxidase available from Sigma-Aldrich company, deriving from the L-amino-acid oxidase of muddy rhodococcus and derive from the sticking mycetozoan L-amino-acid oxidase of product can be with reference to Preparation of d-amino acids by direct fermentative means, Fotheringham, I.G., Taylor, P.P.and Ton, J.L. (1998) US Patent 5728555 and/or Purification and characterization of an l-amino acid deaminase used to prepare unnatural amino acids.Pantaleone, D.P., A.M.Geller, et al. (2001) .Journal of Molecular Catalysis.B, Enzymatic 11 (4-6): the method that 795-803. etc. provide obtains.
Embodiment 1-3, remove the L-L-Ala in the L-2-aminobutyric acid solution
At 25 ℃, pH is controlled to be by soda acid under 8.0 the condition, contain to 500ml and to add alanine racemase and D-amino-acid oxidase in the solution of L-2-aminobutyric acid 30g/L and L-L-Ala 5g/L, carry out conversion reaction with the condition shown in the table 1 then, and the L-2-aminobutyric acid in the difference detection reaction liquid and the content of L-Ala, detected result is as shown in table 2, and the alanine racemase that uses among the embodiment 1-3 is respectively the alanine racemase that derives from subtilis; The D-amino-acid oxidase that uses is respectively the D-amino-acid oxidase that derives from rhodotorula, trigonopsis variabilis and trigonopsis variabilis, wherein, the D-amino-acid oxidase among the embodiment 3 is the immobilization trigonopsis variabilis D-amino-acid oxidase available from Hu'nan Fulaige Biological Technology Co. Ltd.; The catalase that adds among the embodiment 2-3 is available from the outstanding promise biological enzyme in Zaozhuang City company limited.
Table 1, conversion condition
| Embodiment | The alanine racemase enzyme is lived | D-amino-acid oxidase enzyme is lived | Oxygen obtains mode | Stirring velocity |
| ??1 | ??3000U/L | ??3000U/L | 0.1V/VM the speed aerating oxygen | ??200rpm |
| ??2 | ??4000U/L | ??2000U/L | 5000U/L catalase, 0.5ml/min add 20% superoxol | ??200rpm |
| ??3 | ??3000U/L | ??2000U/L | 5000U/L catalase, 0.5ml/min add 20% superoxol | ??200rpm |
Table 2, detected result
According to the result of table 2, in embodiment 1-4, all remove the L-Ala in the solution system effectively, and kept the high yield of target amino acid (L-2-aminobutyric acid), promptly specificly removed the L-Ala in the solution system.
Embodiment 4-5, remove the L-Ala in L-Terleu solution, the L-Xie Ansuan solution
The solution that contains L-Terleu 30g/L and L-L-Ala 6g/L respectively to 100ml, 500ml contains in the solution of L-Xie Ansuan 30g/L and L-L-Ala 4g/L and adds alanine racemase, the catalase of amino-acid oxidase and 5000U/L, adding content with the speed of 0.5ml/min then is 20% superoxol, temperature is controlled at 25 ℃, pH is maintained 8.0, carry out conversion reaction under the condition of 200rpm stirring velocity, then respectively at reacted 4 hours and 6 hours, the target amino acid in the detection reaction liquid and the content of L-Ala, detected result is as shown in table 3, wherein, the alanine racemase that uses among the embodiment 4-5 derives from the alanine racemase of subtilis as 3000U/L; The amino-acid oxidase that uses is respectively 2000U/L and derives from the D-amino-acid oxidase of rhodotorula, the D-amino-acid oxidase that 2000U/L derives from trigonopsis variabilis.
Table 3, detected result
According to the result of table 3, in embodiment 4-5, all remove the L-Ala in the conversion reaction system substantially, and kept the high yield of target amino, promptly specificly removed the L-Ala in the solution system.
Though; the target amino acid of using in the above-mentioned embodiment 1-5 that provides is L-2-aminobutyric acid, L-Terleu, L-Xie Ansuan; but for a person skilled in the art; other neutral amino acids; as L-norvaline, D-Xie Ansuan, D-leucine and D-Terleu etc.; removal L-Ala method provided by the invention has versatility, therefore, also belongs to protection category of the present invention.
According to The above results, most alanine racemases have strict substrate specificity, only L-L-Ala and D-L-Ala are had racemization, thereby have avoided the target amino oxidation, thereby with the amino-acid oxidase acting in conjunction, can specific removal conversion fluid or fermented liquid in L-Ala.Therefore, use method provided by the invention, can remove the conversion fluid of preparation neutral amino acids or the L-Ala in the fermented liquid specifically, and not influence the target amino yield.Because the content of L-Ala is very low in the solution after conversion reaction is handled, thereby can be reduced at neutral target amino separation and purification and the process for refining for preparing in transaminase method and the fermentation method greatly.
Claims (9)
1. the method for L-Ala in the reaction system of removing the preparation neutral amino acids, it is characterized in that, described method comprises and adds alanine racemase and can further catalyst for reaction take place specificity catalysis single chiral amino acid in described reaction system, by the L-Ala in both described reaction systems of common catalytic elimination.
2. the method for claim 1 is characterized in that, described neutral amino acids comprises the L-2-aminobutyric acid, L-Terleu, L-norvaline, L-leucine, L-Xie Ansuan, D-tryptophane, D-leucine, L-Isoleucine, D-Xie Ansuan and D-Terleu.
3. the method for claim 1, it is characterized in that, described alanine racemase is to have the specific alanine racemase of homoamino acid, is selected from: the alanine racemase that derives from subtilis, Corynebacterium glutamicum, Salmonella typhimurium, Pseudomonas aeruginosa, intestinal bacteria or bacillus stearothermophilus.
4. the method for claim 1; it is characterized in that; further catalyst for reaction takes place described energy specificity catalysis single chiral amino acid is the enzyme that has optical specificity, can act on L-L-Ala or D-L-Ala, and these enzymes are selected from: amino-acid oxidase, amino acid acylase and amino amino transaminase.
5. the method for claim 1; it is characterized in that; the target product of described reaction system is a L-amino acid, described can specificity catalysis single chiral amino acid further catalyst for reaction takes place is selected from: D-amino-acid oxidase, D-amino acid acylase, D-amino acid transaminase and D-amino acid had specific esterification enzyme.
6. method as claimed in claim 5, it is characterized in that, described D-amino-acid oxidase is selected from: the D-amino-acid oxidase (pkDAAO) that pig is kidney derived, the D-amino-acid oxidase (TvDAAO) in trigonopsis variabilis source, and the D-amino-acid oxidase (RgDAAO) in rhodotorula source.
7. method as claimed in claim 5, it is characterized in that, described D-amino acid transaminase is selected from: derives from the D-amino acid transaminase of subtilis, derives from the D-amino acid transaminase of Bacillus sphaericus, and the D-amino acid transaminase that derives from the stearothermophilus ground bacillus.
8. the method for claim 1; it is characterized in that; the target product of described reaction system is a D-amino acid, described can specificity catalysis single chiral amino acid further catalyst for reaction takes place is selected from: L-amino-acid oxidase, L-amino acid acylase, L-amino acid aminotransferase and L-amino acid had specific esterification enzyme.
9. method as claimed in claim 8 is characterized in that, described L-amino-acid oxidase is selected from: derive from the L-amino-acid oxidase of muddy rhodococcus, derive from and produce sticking mycetozoan L-amino-acid oxidase, and the L-amino-acid oxidase that derives from the snake class.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104131041A (en) * | 2014-08-01 | 2014-11-05 | 洛阳华荣生物技术有限公司 | Production method for alpha-ketoglutaric acid |
| CN105368913A (en) * | 2015-12-22 | 2016-03-02 | 滨海瀚鸿生化有限公司 | Bi-enzyme preparation method for industrial production of chiral unnatural amino acid |
| WO2018037097A1 (en) | 2016-08-24 | 2018-03-01 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Method for preparing rich culture media for labelling amino acids incorporated into proteins |
| CN107794284A (en) * | 2016-08-29 | 2018-03-13 | 湖州柏特生物科技有限公司 | A kind of method that removal prepares the L threonines in chiral amino acid reaction system |
| CN116590202A (en) * | 2023-07-12 | 2023-08-15 | 欧铭庄生物科技(天津)有限公司滨海新区分公司 | Corynebacterium glutamicum and application thereof in fermentation production of L-leucine |
-
2009
- 2009-03-06 CN CN200910047124.4A patent/CN101824443B/en active Active
Non-Patent Citations (2)
| Title |
|---|
| IAN G. FOTHERINGHAM ET AL: "Engineering of A Novel Biochemical Pathway for the Biosynthesis of L-2-aminobutyric Acid in Escherichia coli K12", 《BIOORGANIC & MEDICINAL CHEMISTRY》 * |
| LI ZHU ET AL: "Removal of L-alanine from the production of L-2-aminobutyric acid by introduction of alanine racemase and D-amino acid oxidase", 《APPL MICROBIOL BIOTECHNOL》 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104131041A (en) * | 2014-08-01 | 2014-11-05 | 洛阳华荣生物技术有限公司 | Production method for alpha-ketoglutaric acid |
| CN105368913A (en) * | 2015-12-22 | 2016-03-02 | 滨海瀚鸿生化有限公司 | Bi-enzyme preparation method for industrial production of chiral unnatural amino acid |
| WO2018037097A1 (en) | 2016-08-24 | 2018-03-01 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Method for preparing rich culture media for labelling amino acids incorporated into proteins |
| FR3055337A1 (en) * | 2016-08-24 | 2018-03-02 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | PROCESS FOR THE PREPARATION OF RICH CULTURING MEDIA FOR THE MARKING OF AMINO ACIDS INCORPORATED IN PROTEINS |
| CN107794284A (en) * | 2016-08-29 | 2018-03-13 | 湖州柏特生物科技有限公司 | A kind of method that removal prepares the L threonines in chiral amino acid reaction system |
| CN116590202A (en) * | 2023-07-12 | 2023-08-15 | 欧铭庄生物科技(天津)有限公司滨海新区分公司 | Corynebacterium glutamicum and application thereof in fermentation production of L-leucine |
| CN116590202B (en) * | 2023-07-12 | 2023-09-12 | 欧铭庄生物科技(天津)有限公司滨海新区分公司 | Corynebacterium glutamicum and application thereof in fermentation production of L-leucine |
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