CN106480009A - A kind of immobilized alpha-amino-acid ester acyltransferase and the application in preparing glutamine dipeptide - Google Patents
A kind of immobilized alpha-amino-acid ester acyltransferase and the application in preparing glutamine dipeptide Download PDFInfo
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- CN106480009A CN106480009A CN201611211842.7A CN201611211842A CN106480009A CN 106480009 A CN106480009 A CN 106480009A CN 201611211842 A CN201611211842 A CN 201611211842A CN 106480009 A CN106480009 A CN 106480009A
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- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
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- C12N9/104—Aminoacyltransferases (2.3.2)
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- C12P21/00—Preparation of peptides or proteins
- C12P21/02—Preparation of peptides or proteins having a known sequence of two or more amino acids, e.g. glutathione
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Abstract
The present invention relates to a kind of immobilized alpha-amino-acid ester acyltransferase and its preparation method and application, the immobilized alpha-amino-acid ester acyltransferase that the present invention provides by amino-acid ester acyltransferase to adsorb, covalent bond, the fixed form of embedding, microencapsulation or crosslinking be fixed in fixed enzyme vector and be prepared from, wherein, the mass percent that described amino-acid ester acyltransferase accounts for described fixed enzyme vector is 0.01% ~ 5%.The immobilized enzyme of the present invention, compared with liquid enzyme, reduces production cost and labor intensity, improves utilization ratio and the product quality of enzyme, reduces three wastes row, environmental protection.In addition, described immobilized enzyme easily separates from reaction liquid mixture, reuse；Reactor design is more flexible；It is suitable for multiple different reaction mediums and response system；Facilitate process development and downstream processes, particularly convenient for process control.
Description
Technical field
The invention belongs to pharmaceutical chemistry technical field, it is specifically related to a kind of immobilized alpha-amino-acid ester acyltransferase, its system
Preparation Method, and the method that glutamine dipeptide is prepared using this immobilized alpha-amino-acid ester acyltransferase.
Background technology
Glutamine dipeptide（N-（2）- Ala-Gln）Than L-Glutamine, there is higher stability in aqueous
It is widely used in injection and serum-free medium with dissolubility.L-Glutamine has particularly important physiological function and pharmacology is made
With so as to the application in parenteral nutrition is subject to the most attention of people.Glutamine dipeptide resolves into rapidly paddy after entering human body
Glutamine and play a role, research has shown that, glutamine dipeptide has and is broken down into alanine and L-Glutamine quickly in vivo, and the half-life is very
Short, it is only able to detect a small amount of dipeptides in blood, only micro dipeptides is discharged from urine, illustrates that glutamine dipeptide can be effective
It is utilized and will not gather in blood, it is to avoid issuable pharmacology and physiological damage.
Chemical method synthesis glutamine dipeptide synthesis complex course is long, and environmental pollution is big, high cost.Production by Enzymes glutamine dipeptide work
Skill is simple, environmental protection, low cost.Mostly reacted using liquid enzyme at present, compared with using immobilized enzyme, every batch reaction must
New enzyme liquid must be used instead, separate difficult, complex operation, and reduce the utilization ratio of enzyme, waste liquid is not recyclable, produce a large amount of three
Useless pollutant, may contain the thalline impurity such as albumen simultaneously in product.
The development history of existing more than 100 year of enzyme immobilization technology, to eighties of last century end of the seventies, this technology is suitable
Maturation, selects suitable process for fixation such as investment, microencapsulation, is covalently attached method, absorption method or combined method, suitable
Carrier such as inorganic carrier or organic carrier, natural carrier or synthetic vectors, porous carrier or non-porous support, film, granule, foam,
Capsule etc., and suitable fixing condition such as aqueous phase, organic solvent, pH, temperature etc..With scientific and technical development, fixing
The technology changing enzyme also constantly improves again, by updating of fixation support, process for fixation and enzyme, improves many not
There is the performance of industrial applications enzyme so as to have higher selectivity, vigor and ruggedness.By the use of immobilized enzyme,
Facilitate the separation of reactant mixture, reactor design is relatively flexibly it is adaptable to multiple differential responses media and response system, convenient
Process development and downstream processes, particularly convenient for process control.But, a lot of industrial reactions shorter due to being applied to the industry time, especially
It is also to be provided without enzyme immobilization technology in some medicine intermediates preparation technology.
Content of the invention
The technical problem to be solved is to overcome existing technical deficiency, provides a kind of immobilized alpha-amino-acid ester acyl
Transferring enzyme.
For solve problem above, the present invention adopt the following technical scheme that for：
A kind of immobilized alpha-amino-acid ester acyltransferase, its by amino-acid ester acyltransferase to adsorb, covalent bond, embedding, microcapsule
The fixed form of change or crosslinking is fixed in fixed enzyme vector and is prepared from, and wherein, described amino-acid ester acyltransferase accounts for institute
The mass percent stating fixed enzyme vector is 0.01% ~ 5%.
Preferably, immobilized alpha-amino-acid ester acyltransferase of the present invention, wherein, described amino-acid ester acyltransferase accounts for
The mass percent of described fixed enzyme vector is 0.1% ~ 2.5%.
Immobilized alpha-amino-acid ester acyltransferase of the present invention, wherein, described amino-acid ester acyltransferase is wild type
Or saltant type.
Further, immobilized alpha-amino-acid ester acyltransferase of the present invention, wherein, described fixed form is covalent knot
Close, described fixed enzyme vector is selected from epoxy base immobilized enzyme vector or amino fixed enzyme vector.
Further, immobilized alpha-amino-acid ester acyltransferase of the present invention, wherein, described immobilized alpha-amino-acid ester acyl
The preparation method of transferring enzyme is：Amino-acid ester acyltransferase and fixed enzyme vector are separately added in buffer solution, described slow
The pH value rushing liquid is 5 ~ 10, controls immobilized reactant temperature to be 5 ~ 40 DEG C, and stirring reaction 5 ~ 72 hours is collected solid, is dried, that is,
?.
Preferably, immobilized alpha-amino-acid ester acyltransferase of the present invention, wherein, the pH value of described buffer solution is 7 ~
9, more preferably 8, described immobilized reactant temperature is 15 DEG C ~ 25 DEG C, more preferably 20 DEG C, described buffer solution choosing
From phosphate buffered solution, Tris-HCL buffer solution or triethanolamine buffer solution.
Another object of the present invention is to providing the biological preparation method producing glutamine dipeptide using above-mentioned immobilized enzyme.
The present invention provide technical scheme be：
A kind of method that immobilized alpha-amino-acid ester acyltransferase using the present invention prepares glutamine dipeptide as biocatalyzer, its
With L-Glutamine and L-Alanine methyl ester or L-Alanine methyl ester hydrochloride as substrate, it is 5.0 ~ 9.5 aqueous phase solution in pH value
In, under 5 DEG C ~ 30 DEG C of reaction temperature, stirring, make immobilization amino any one of in claim 1 ~ 4 for two kinds of substrates
React under the catalytic action of acid esters acyltransferase generation glutamine dipeptide.
Preferably, the method preparing glutamine dipeptide of the present invention, in reaction system when its reaction is initial, described paddy
The concentration of glutamine is 1% ~ 25%, unit g/mL, the concentration of described L-Alanine methyl ester or L-Alanine methyl ester hydrochloride is 1% ~
25%, unit g/mL, the concentration of described immobilized alpha-amino-acid ester acyltransferase is 1% ~ 25%, unit g/mL.
It is further preferred that the preparation method of glutamine dipeptide of the present invention, institute in reaction system when its reaction is initial
Stating L-Alanine methyl ester or the concentration of L-Alanine methyl ester hydrochloride is 5% ~ 25%, unit g/mL, the concentration of described L-Glutamine
For 5% ~ 15%, unit g/mL.
Preferably, the preparation method of glutamine dipeptide of the present invention, in the initial system of its reaction, described immobilization amino
The concentration of acid esters acyltransferase is 5% ~ 15%, unit g/mL.
Preferably, the preparation method of glutamine dipeptide of the present invention, in reaction system when its reaction is initial, described water
The pH value of phase solution is 7.0 ~ 9.5.
Preferably, the preparation method of glutamine dipeptide of the present invention, in reaction system when its reaction is initial, described anti-
Answer 5 DEG C ~ 20 DEG C of temperature.
Preferably, the preparation method of glutamine dipeptide of the present invention, wherein, described aqueous phase solution is buffer solution.
Substrate used by the present invention（L-Alanine methyl ester or L-Alanine methyl ester hydrochloride, L-Glutamine）, amino-acid ester
Acyltransferase, fixed enzyme vector etc. are all commercially available.
The implementation process of preparation method of the present invention is as follows：Add buffer solution in reaction vessel, sequentially add bottom
Thing L-Alanine methyl ester or L-Alanine methyl ester hydrochloride, L-Glutamine, immobilized alpha-amino-acid ester acyltransferase, in 5 DEG C of temperature ~
Stirring reaction at 30 DEG C, using the product of high performance liquid chromatography monitoring reaction, reaches more than 80% terminating reaction to conversion ratio.
All features disclosed in this specification, or disclosed all methods or during step, except mutually exclusive
Feature and/or step beyond, all can combine by any way.
Compared with the prior art the present invention has following advantage：
1st, the inventive method is passed through to add cheap and wide material sources adjuvants, improve efficiently in traditional enzyme catalysiss production process
Concentration of substrate is low, enzyme reaction is the shortcomings of time-consuming, realize efficiently, low cost prepare glutamine dipeptide.
2nd, the immobilized enzyme of the present invention, compared with liquid enzyme, reduces production cost and labor intensity, improves the utilization ratio of enzyme
And product quality, reduce three wastes row, environmental protection.
3rd, immobilized enzyme easily separates from reaction liquid mixture, reuses；Reactor design is more flexible；It is suitable for many
Plant different reaction mediums and response system；Facilitate process development and downstream processes, particularly convenient for process control.
Specific embodiment
With reference to specific embodiment, the present invention will be further described in detail, but the present invention is not limited to following enforcement
Example.
The preparation of embodiment 1 immobilized alpha-amino-acid ester acyltransferase
Take 250mL there-necked flask, plus 150mL phosphate buffered solution（100mM, pH value 8.0）, and sequentially add 1g aminoacid
Ester acyltransferase（Or liquid enzymes）, 40g epoxy base immobilized enzyme vector（sepabeads® EC-EP113-M）, 20 DEG C of temperature,
Rotating speed 150rpm, reacts 24 hours, collects immobilized enzyme.
The preparation of embodiment 2 immobilized alpha-amino-acid ester acyltransferase
Take 250mL there-necked flask, plus 150mL phosphate buffered solution（100mM, pH value 8.0）, and sequentially add 1g aminoacid
Ester acyltransferase（Or liquid enzymes）, 40g activation after amino fixed enzyme vector（sepabeads® EC-HA/M）, temperature 20
DEG C, rotating speed 150rpm, reacts 24 hours, collects immobilized enzyme.
The preparation of embodiment 3 immobilized alpha-amino-acid ester acyltransferase
Take 250mL there-necked flask, plus 150mL phosphate buffered solution（100mM, pH value 8.0）, and sequentially add 0.04g amino
Acid esters acyltransferase（Or liquid enzymes）, 40g activation after amino fixed enzyme vector（sepabeads® EC-HA/M）, temperature
20 DEG C, rotating speed 150rpm, reacts 36 hours, collects immobilized enzyme.
The enzyme process preparation of embodiment 4 glutamine dipeptide
Substrate L-Alanine methyl ester hydrochloride 17.25g, 8 grams of L-Glutamine, purified water is added in 250mL there-necked flask
150mL, embodiment 1 immobilized alpha-amino-acid ester acyltransferase 10g, at 20 DEG C, 200rpm stirring reaction, with 6moL/L hydrochloric acid control
PH value 8.5 processed, using the conversion ratio of liquid chromatograph monitoring reaction, after 30 minutes, conversion ratio reaches more than 80%, and separation and recovery is fixed
Change enzyme.
Above-mentioned immobilized enzyme is reused 10 times, and the response time is less than 1 hour, and conversion ratio is more than 80%.
The enzyme process preparation of experimental example 5 glutamine dipeptide
Substrate L-Alanine methyl ester hydrochloride 17.25g, 8 grams of L-Glutamine, purified water is added in 250mL there-necked flask
150mL, embodiment 2 immobilized alpha-amino-acid ester acyltransferase 10g, at 20 DEG C, 200rpm stirring reaction, with 6moL/L hydrochloric acid control
PH value 8.5 processed, using the conversion ratio of liquid chromatograph monitoring reaction, after 30 minutes, conversion ratio reaches more than 80%, and separation and recovery is fixed
Change enzyme.
Above-mentioned immobilized enzyme is reused 10 times, and the response time is less than 1 hour, and conversion ratio is more than 80%.
Claims (10)
1. a kind of immobilized alpha-amino-acid ester acyltransferase it is characterised in that：By amino-acid ester acyltransferase to adsorb, covalently tie
Close, the fixed form of embedding, microencapsulation or crosslinking is fixed in fixed enzyme vector and is prepared from, wherein, described amino-acid ester
The mass percent that acyltransferase accounts for described fixed enzyme vector is 0.01% ~ 5%.
2. immobilized alpha-amino-acid ester acyltransferase according to claim 1 it is characterised in that：Described fixed form is covalent
In conjunction with described fixed enzyme vector is selected from epoxy base immobilized enzyme vector or amino fixed enzyme vector, described amino-acid ester acyl
The mass percent that transferring enzyme accounts for described fixed enzyme vector is 0.1% ~ 2.5%.
3. the immobilized alpha-amino-acid ester acyltransferase according to claim 2 it is characterised in that：Described immobilization aminoacid
The preparation method of ester acyltransferase is：Amino-acid ester acyltransferase and fixed enzyme vector are separately added in buffer solution, institute
The pH value stating buffer is 5 ~ 10, controls immobilized reactant temperature to be 5 ~ 40 DEG C, and stirring reaction 5 ~ 72 hours is collected solid, done
Dry, obtain final product.
4. immobilized alpha-amino-acid ester acyltransferase according to claim 3 it is characterised in that：The pH value of described buffer solution
For 7 ~ 9, described immobilized reactant temperature is 15 DEG C ~ 25 DEG C, and described buffer solution is selected from phosphate buffered solution, Tris-HCL delays
Rush solution or triethanolamine buffer solution.
5. a kind of immobilized alpha-amino-acid ester acyltransferase adopting any one of claim 1 ~ 4 is as biocatalyzer system
The preparation method of standby glutamine dipeptide it is characterised in that：With L-Glutamine and L-Alanine methyl ester or L-Alanine methyl ester hydrochloride
For substrate, in the aqueous phase solution for 5.0 ~ 9.5 for the pH value, under 5 DEG C ~ 30 DEG C of reaction temperature, stir, make two kinds of substrates in right
Require to react under the catalytic action of immobilized alpha-amino-acid ester acyltransferase any one of 1 ~ 4 generation glutamine dipeptide.
6. glutamine dipeptide according to claim 5 preparation method it is characterised in that：Reaction system when reaction is initial
In, the concentration of described L-Glutamine is 1% ~ 25%, unit g/mL, described L-Alanine methyl ester or L-Alanine methyl ester hydrochloride
Concentration is 1% ~ 25%, unit g/mL, and the concentration of described immobilized alpha-amino-acid ester acyltransferase is 1% ~ 25%, unit g/mL.
7. glutamine dipeptide according to claim 6 preparation method it is characterised in that：Institute in reaction system when reaction is initial
Stating L-Alanine methyl ester or the concentration of L-Alanine methyl ester hydrochloride is 5% ~ 25%, unit g/mL, the concentration of described L-Glutamine
For 5% ~ 15%, unit g/mL.
8. glutamine dipeptide according to claim 5 preparation method it is characterised in that：In the initial system of reaction, described solid
Surely the concentration changing amino-acid ester acyltransferase is 5% ~ 15%, unit g/mL.
9. glutamine dipeptide according to claim 5 preparation method it is characterised in that：Reaction system when reaction is initial
In, the pH value of described aqueous phase solution is 7.0 ~ 9.5.
10. glutamine dipeptide according to claim 5 preparation method it is characterised in that：Reaction system when reaction is initial
In, 5 DEG C ~ 20 DEG C of described reaction temperature.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201611211842.7A CN106480009B (en) | 2016-12-25 | 2016-12-25 | Immobilized amino acid ester acyl transferase and application thereof in preparation of glutamine dipeptide |
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| CN201611211842.7A CN106480009B (en) | 2016-12-25 | 2016-12-25 | Immobilized amino acid ester acyl transferase and application thereof in preparation of glutamine dipeptide |
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| CN106480009B CN106480009B (en) | 2020-12-11 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108728424A (en) * | 2018-06-26 | 2018-11-02 | 河北善泉生物科技有限公司 | The method that one step purifies immobilization ɑ-amino acid acyltransferase |
| CN113817790A (en) * | 2021-10-18 | 2021-12-21 | 精晶药业股份有限公司 | Method for preparing alanyl glutamine by immobilized enzyme |
Citations (3)
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| WO2008126783A1 (en) * | 2007-04-06 | 2008-10-23 | Kyowa Hakko Bio Co., Ltd. | Method for producing dipeptide |
| CN105754983A (en) * | 2016-05-19 | 2016-07-13 | 河北周酶生物科技有限公司 | Immobilized enzyme for preparing Ezetimibe midbody and preparation method of immobilized enzyme |
| CN105925558A (en) * | 2016-05-17 | 2016-09-07 | 河北周酶生物科技有限公司 | Compound immobilized enzyme used for preparing statins and preparation method of compound immobilized enzyme |
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2016
- 2016-12-25 CN CN201611211842.7A patent/CN106480009B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008126783A1 (en) * | 2007-04-06 | 2008-10-23 | Kyowa Hakko Bio Co., Ltd. | Method for producing dipeptide |
| CN105925558A (en) * | 2016-05-17 | 2016-09-07 | 河北周酶生物科技有限公司 | Compound immobilized enzyme used for preparing statins and preparation method of compound immobilized enzyme |
| CN105754983A (en) * | 2016-05-19 | 2016-07-13 | 河北周酶生物科技有限公司 | Immobilized enzyme for preparing Ezetimibe midbody and preparation method of immobilized enzyme |
Non-Patent Citations (1)
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| 何艳春: "产α-氨基酸酯酰基转移酶重组大肠杆菌的构建及发酵优化", 《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108728424A (en) * | 2018-06-26 | 2018-11-02 | 河北善泉生物科技有限公司 | The method that one step purifies immobilization ɑ-amino acid acyltransferase |
| CN108728424B (en) * | 2018-06-26 | 2021-09-14 | 河北善泉生物科技有限公司 | Method for purifying immobilized alpha-amino acid lipid acyltransferase by one step |
| CN113817790A (en) * | 2021-10-18 | 2021-12-21 | 精晶药业股份有限公司 | Method for preparing alanyl glutamine by immobilized enzyme |
| CN113817790B (en) * | 2021-10-18 | 2023-11-03 | 精晶药业股份有限公司 | Method for preparing alanyl glutamine by immobilized enzyme |
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