CN109136295A - A kind of method of biosynthesis glutaric acid - Google Patents
A kind of method of biosynthesis glutaric acid Download PDFInfo
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- CN109136295A CN109136295A CN201810942280.6A CN201810942280A CN109136295A CN 109136295 A CN109136295 A CN 109136295A CN 201810942280 A CN201810942280 A CN 201810942280A CN 109136295 A CN109136295 A CN 109136295A
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- C12Y102/01—Oxidoreductases acting on the aldehyde or oxo group of donors (1.2) with NAD+ or NADP+ as acceptor (1.2.1)
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- C12Y401/00—Carbon-carbon lyases (4.1)
- C12Y401/01—Carboxy-lyases (4.1.1)
- C12Y401/01018—Lysine decarboxylase (4.1.1.18)
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Abstract
The invention discloses a kind of methods of biosynthesis glutaric acid, it include 5 enzymes in route of synthesis, it is respectively as follows: lysine decarboxylase (cadA), pentanediamine transaminase (patA), 5- aminovaleric acid semialdehyde dehydrogenase (patD), 5- aminovaleric acid transaminase (gabT) and glutarate-semialdehyde dehydrogenase (gabD).The encoded gene of these enzymes is expressed in host, as a result obtains the production host that can use lysine production glutaric acid.Said gene is imported into lysine high-yielding strain, realizes the de novo formation of glutaric acid.It is to promote extracellular intermediate to intracellular transport, so that the production of glutaric acid is highly efficient by co-expressing pentanediamine transport protein and 5- aminovaleric acid transport protein in engineering bacteria simultaneously the invention also discloses a kind of method of reinforcement glutaric acid production.The method of the present invention application prospect great for the industrial production of glutaric acid.
Description
Technical field
The present invention relates to field of biotechnology, and more precisely, the present invention relates to a kind of sides of bioanalysis production glutaric acid
Method additionally relates to one kind by co-expressing pentanediamine transport protein and 5- aminovaleric acid transport protein in engineering bacteria, adds
The method of fast glutaric acid production.
Background technique
Glutaric acid (1,5-pentanedioic acid, Glutarate) is a kind of aliphatic dicarboxylic acid, and molecular formula is
C5H8O4, molecular weight 132.11, structural formula:Soluble easily in water, ethyl alcohol, ether etc., solubility is reachable in water
430g·L-1.In all dicarboxylic acids, the fusing point of glutaric acid is minimum, is 95-98 DEG C, this good characteristic is more suitable for it
C5 dicarboxylic acid structural units for important polymers such as nylon -4,5 and nylon -5,5.Before it is also 1,5- pentanediol simultaneously
Body, 1,5-PD are used as the common plasticizers of scaling powder activator and pharmaceutical intermediate.So glutaric acid is in drug and change
Work, which synthesizes field, has important application value.
There are many kinds of the chemical synthesis process of glutaric acid, can industrially recycle, test from the byproduct of production adipic acid
Room can be used as substrate from gamma-butyrolacton, dihydropyran, glutaronitrile, cyclohexanone etc. respectively, be prepared by series of chemical
?.However it is high to have the shortcomings that at high cost, seriously polluted, operating condition requires by conventional chemical methods synthesizing glutaric acid.It is existing
Glutaric acid biosynthesis pathway there is also the disadvantages such as low output, conversion ratio be low.Therefore new glutaric acid biosynthesis side is developed
Method has a very important significance the high molecular polymers such as synthesizing polyamides and polyurethane.
Present invention is primarily aimed at realization bioanalysis to prepare efficiently synthesizing for glutaric acid.It is higher catalytic efficiency has been screened
Enzyme realizes the production of glutaric acid, and the new metabolic pathway of same engineer realizes the de novo formation of glutaric acid.In addition originally
Invention also discloses a kind of coexpression pentanediamine transport protein and the method for 5- aminovaleric acid transport protein accelerates glutaric acid
Production.The experimental results showed that with optimal conditions, engineered strain can produce in shaking flask using lysine or glucose
The glutaric acid of 3.74 ± 0.06g/L and 8.60 ± 0.11g/L.
Summary of the invention
The object of the present invention is to provide the hosts of high yield glutaric acid, by bacterium original or being transformed, fungi
The enzyme being overexpressed in efficiently production glutaric acid approach, is preferably derived from bacterium, and the lysine that fungi or protein engineering are transformed is de-
Carboxylic acid cadA, pentanediamine transaminase patA, 5- aminovaleric acid semialdehyde dehydrogenase patD, 5- aminovaleric acid transaminase gabT and penta 2
Sour semialdehyde dehydrogenase gabD realizes conversion of the glutaric acid from lysine by the high efficient expression of these enzymes in host.
Another object of the present invention is to select pentanediamine transport protein, and 5- aminovaleric acid transport protein carries out intermediate product
Transhipment adjust, solve the problems, such as that intermediate product is largely accumulated in fermentation liquid and cannot be utilized again, and achieve
Significant effect.
A further object of the present invention is the synthesis by enhancing precursor lysine, and then realizes the slave glucose of glutaric acid
This simple carbon source efficiently synthesizes.
To achieve the goals above, the present invention provides the host that can produce glutaric acid, in bacterium original or being transformed,
It is overexpressed gene in glutaric acid synthesis path in fungal cell, prepares the conversion host of the glutaric acid.
The present invention also provides the methods that microorganism produces glutaric acid: the first is external addition lysine, to original or change
The bacterium made imports coding lysine decarboxylase cadA, pentanediamine transaminase patA, 5- aminovaleric acid semialdehyde in fungal cell
Dehydrogenase patD, 5- aminovaleric acid transaminase gabT, the gene of glutarate-semialdehyde dehydrogenase gabD, and ferment.From fermentation
It samples in liquid, is analyzed using concentration of the high performance liquid chromatography to intermediate product and target product；Second is glutaric acid
De novo formation, enhancing precursor lysine synthesis be transferred to fermentation medium after being incubated overnight the host for producing glutaric acid
In, the concentration of intermediate product and target product is measured with high performance liquid chromatography.
The present invention also provides the methods of microbe high-yield glutaric acid, specifically have following several: first is excellent by modularization
Change the expression intensity for adjusting modules, stablize and improves glutaric acid yield.Second be coexpression pentanediamine transport protein with
And 5- aminovaleric acid transport protein carries out the transhipment adjusting of intermediate product, accelerates intermediate product from extracellular to intracellular transport, solves
The problem of intermediate product extracellular accumulation, and achieve significant effect.Final glutaric acid adds in vitro and de novo formation yield
Respectively reach 3.74 ± 0.06g/L and 8.60 ± 0.11g/L.
As described above, the present invention relates to effective production method of glutaric acid, the method is characterized by original
The bacterium for beginning or being transformed, the relevant enzyme being overexpressed in fungal cell in efficiently production glutaric acid approach, coexpression pentanediamine turn
Albumen and 5- aminovaleric acid transport protein are transported, to realize the efficient de novo formation of glutaric acid.
Detailed description of the invention
Fig. 1 produces glutaric acid mechanism of action schematic diagram using genetic engineering bacterium；
Fig. 2 modularization optimum results figure；BM1:BW(pSA-cadA,pCS-patAD-gabTD)
Fig. 3 co-expresses pentanediamine transport protein potE and 5- aminovaleric acid transport protein gabP and improves glutaric acid yield knot
Fruit figure；BM2:BW(pSA-cadA-potE,pCS-patAD-gabTDP)
Fig. 4 realizes the de novo formation of glutaric acid using genetic engineering；BM3:BW(pSA-cadA-potE,pCS-patAD-
gabTDP,pZE-lysA-dapB-lysCfbr)
Specific embodiment
Below in conjunction with attached drawing, the present invention will be further described with embodiment:
In the present invention, there is no particular/special requirement to the type of expression plasmid, it is believed that in expression in escherichia coli target gene
Construction method can use various methods commonly used in the art, target gene is such as connected to carrier after digestion is handled,
It repeats no more later.
In following embodiment, coli strain Trans5 α, BW25113 are common coli strain, the city Jun Ke
Acquisition is sold, wherein Trans5 α is used for vector construction, and BW25113 is then used as fermentation bacterial strain.
Specific embodiment 1
Glutaric acid produces the modularization optimization of bacterial strain
The lysine decarboxylase cadA of Escherichia coli is selected, pentanediamine transaminase patA, 5- aminovaleric acid semialdehyde is de-
Hydrogen enzyme patD, 5- aminovaleric acid transaminase gabT, glutarate-semialdehyde dehydrogenase gabD, PCR acquisition genetic fragment, then uses nucleic acid
Restriction endonuclease carries out double digestion to segment and carrier, and the segment after digestion is carried out glue recycling or column recycles, later by target gene
It is inserted respectively into plasmid pZE12-luc (height copy), on pCS27 (middle copy), pSA74 (low-copy).Adjust the expression of gene
Amount detects the accumulation of target product and intermediate product, has carried out modularization optimization to host strain, has obtained pSA-cadA,
PCS-patAD-gabTD recombinant plasmid (table 1).
The cell of electric robin preparation competence, and dispense 100 μ L in 1.5mL EP pipe for converting.The weight that will be built
Group plasmid pSA-cadA 2 μ L and pCS-patAD-gabTD 2 μ L be added to the 1.5mL containing 100 μ L competent cells centrifugation
Guan Zhong is uniformly mixed.Plasmid electricity is rotated into competent cell followed by electroporation.After the completion of electricity turns, LB culture is added
Base, and mixture is transferred in 1.5mL centrifuge tube, recovery 30-60min.Bacterium solution is coated onto the plate containing antibiotic later
On, 37 DEG C are incubated overnight.It is prepared into the bacterial strain BM1:BW (pSA-cadA, pCS-patAD-gabTD) of production glutaric acid.
The fermentation of modularization optimization bacterial strain
Production glutaric acid bacterial strain BM1 plate on pick them separately single colonie, be connected to 4mL with resistant liquid LB
In, 10h is cultivated at 37 DEG C, bacterium solution is transferred in the fermentation medium of 50mL respectively later, be added the IPTG of 0.25-1mM into
Row induction, and add substrate lysine.It is sampled later in 12,24,48,72h and measures intermediate product with high performance liquid chromatography
And the concentration of target product.Ultimate output is as shown in Figure 2.
Specific embodiment 2
It co-expresses pentanediamine transport protein potE, 5- aminovaleric acid transport protein gabP and accelerates glutaric acid synthesis
The potE of Escherichia coli is selected, 5- aminovaleric acid transport protein gabP, PCR acquisition segment then uses nucleic acid
Restriction endonuclease carries out digestion to segment and carrier, and the segment after digestion is carried out glue recycling or column recycles, later by target gene
PotE, gabP are inserted on plasmid pSA-cadA and pCS-patAD-gabTD, obtain pSA-cadA-potE and pCS-patAD-
GabTDP recombinant plasmid (table 1).
The cell of electric robin preparation competence, and dispense 100 μ L in 1.5mL EP pipe for converting.The weight that will be built
Group each 2 μ L of plasmid pSA-cadA-potE and pCS-patAD-gabTDP be added to the 1.5mL containing 100 μ L competent cells from
In heart pipe, it is uniformly mixed.Plasmid electricity is rotated into competent cell followed by electroporation.After the completion of electricity turns, LB training is added
Base is supported, and mixture is transferred in 1.5mL centrifuge tube, recovery 30-60min.Bacterium solution is coated onto later flat containing antibiotic
On plate, 37 DEG C are incubated overnight.It is prepared into bacterial strain BM2:BW (pSA-cadA-potE, the pCS-patAD- of production glutaric acid
gabTDP)。
The fermentation of BW (pSA-cadA-potE, pCS-gabTD-gabTDP)
The picking single colonie on the plate of the bacterial strain BM2 of production glutaric acid, be connected to 4mL in resistant liquid LB,
10h is cultivated at 37 DEG C, bacterium solution is transferred in the fermentation medium of 50mL respectively later, and the IPTG that 0.25-1mM is added is lured
It leads, and adds substrate lysine.Later respectively 12,24,48,72h sampling and with high performance liquid chromatography measure intermediate product and
The concentration of glutaric acid.Ultimate output is as shown in Figure 3.
Specific embodiment 3
The building of engineered strain de novo formation glutaric acid metabolic pathway
After realizing bioconversion lysine synthesizing glutaric acid, by enhancing enzyme lysA, the dapB of upstream lysine flux,
lysCfbrExpression the de novo formation of glutaric acid can be realized.Genetic fragment is obtained with PCR, then with endonuclease to segment
Digestion is carried out with carrier, the segment after digestion is subjected to glue recycling or column recycles, target gene is inserted into plasmid later
On pZE12-luc, pZE-lysA-dapB-lysC is obtainedfbr(table 1).
The cell of electric robin preparation competence, and dispense 100 μ L in 1.5mL EP pipe for converting.The weight that will be built
Group plasmid pZE-lysA-dapB-lysCfbr2 μ L are added in the 1.5mL centrifuge tube containing 100 μ L competent cells, and mixing is equal
It is even.Plasmid electricity is rotated into competent cell followed by electroporation.After the completion of electricity turns, LB culture medium is added, and will mixing
Object is transferred in 1.5mL centrifuge tube, recovery 30-60min.Bacterium solution is coated on the plate containing antibiotic later, 37 DEG C overnight
Culture.It is prepared into bacterial strain BM3:BW (pSA-cadA-potE, pCS-patAD-gabTDP, the pZE-lysA- of production glutaric acid
dapB-lysCfbr)。
BW(pSA-cadA-potE,pCS-patAD-gabTDP,pZE-lysA-dapB-lysCfbr) fermentation
The picking single colonie on the plate of the bacterial strain BM3 of production glutaric acid, be connected to 4mL in resistant liquid LB,
10h is cultivated at 37 DEG C, later respectively by bacterium solution be transferred to 50mL in resistant fermentation medium, be added 0.25-1mM's
IPTG is induced, and adds substrate lysine.It samples 12,24,48,72h and is measured with high performance liquid chromatography respectively later
The concentration of intermediate product and glutaric acid.Ultimate output is as shown in Figure 4.
1 bacterial strain of table and plasmid
Claims (5)
1. a kind of method of biosynthesis glutaric acid, it is characterised in that:, enzyme involved in synthesis path, including lysine decarboxylation
Enzyme cadA, pentanediamine transaminase patA, 5- aminovaleric acid semialdehyde dehydrogenase patD, 5- aminovaleric acid transaminase gabT and penta 2
Sour semialdehyde dehydrogenase gabD.
2. the method according to claim 1, wherein enzyme source involved in synthesis path is in bacterium, fungi or
Protein engineering transformation, encodes lysine decarboxylase cadA, pentanediamine transaminase patA, 5- aminovaleric acid semialdehyde dehydrogenase
The gene of patD, 5- aminovaleric acid transaminase gabT and glutarate-semialdehyde dehydrogenase gabD.
3. the method according to claim 1, wherein the host of production ways, including Escherichia coli, withered grass gemma
Bacillus, Corynebacterium glutamicum, saccharomyces cerevisiae also include the bacterium being transformed, fungi.
4. the method according to claim 1, wherein under the gene expression element of the host of Biosynthetic pathway is
One of state 1), 2) and 3):
1) express downstream pathway, derive from bacterium, fungi or protein engineering transformation, encode lysine decarboxylase cadA, penta 2
Amine transaminase patA, 5- aminovaleric acid semialdehyde dehydrogenase patD, 5- aminovaleric acid transaminase gabT and glutarate-semialdehyde dehydrogenase
The gene of gabD；
2) upstream pathway is expressed, realizes the synthesis of precursor lysine；
1) and 2) 3) expression simultaneously.
5. fungi carries out fermenting experiment as host, real the method according to claim 1, wherein selecting bacterium
Test the optimization of condition: culture produces the host of glutaric acid in the culture medium containing glucose, yeast powder, by total in engineering bacteria
Pentanediamine transport protein and 5- aminovaleric acid transport protein are expressed, the transhipment of intermediate product is accelerated.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112226398A (en) * | 2020-10-30 | 2021-01-15 | 江南大学 | Recombinant escherichia coli for efficiently producing glutaric acid and construction method thereof |
| CN114921502A (en) * | 2022-04-21 | 2022-08-19 | 东华大学 | Method for producing glutaric acid by performing feedback regulation and control on nitrogen source feeding based on microbial physiological parameters |
| CN115109805A (en) * | 2022-03-29 | 2022-09-27 | 东华大学 | Method for preparing 5-amino-1-pentanol by microorganisms |
| CN115261293A (en) * | 2021-04-29 | 2022-11-01 | 北京化工大学 | Genetic engineering bacterium for producing hydroxyadipic acid |
| CN115404192A (en) * | 2021-05-26 | 2022-11-29 | 北京化工大学 | Engineering bacterium for synthesizing 5-amino-1-pentanol and 1,5-pentanediol and application |
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| CN106367445A (en) * | 2016-08-25 | 2017-02-01 | 南京工业大学 | Method of whole-cell-biocatalytically producing glutaric acid |
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| CN106367445A (en) * | 2016-08-25 | 2017-02-01 | 南京工业大学 | Method of whole-cell-biocatalytically producing glutaric acid |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112226398A (en) * | 2020-10-30 | 2021-01-15 | 江南大学 | Recombinant escherichia coli for efficiently producing glutaric acid and construction method thereof |
| CN112226398B (en) * | 2020-10-30 | 2022-08-30 | 江南大学 | Recombinant escherichia coli for efficiently producing glutaric acid and construction method thereof |
| CN115261293A (en) * | 2021-04-29 | 2022-11-01 | 北京化工大学 | Genetic engineering bacterium for producing hydroxyadipic acid |
| CN115261293B (en) * | 2021-04-29 | 2024-02-02 | 北京化工大学 | Genetically engineered bacterium for producing hydroxy adipic acid |
| CN115404192A (en) * | 2021-05-26 | 2022-11-29 | 北京化工大学 | Engineering bacterium for synthesizing 5-amino-1-pentanol and 1,5-pentanediol and application |
| CN115109805A (en) * | 2022-03-29 | 2022-09-27 | 东华大学 | Method for preparing 5-amino-1-pentanol by microorganisms |
| CN114921502A (en) * | 2022-04-21 | 2022-08-19 | 东华大学 | Method for producing glutaric acid by performing feedback regulation and control on nitrogen source feeding based on microbial physiological parameters |
| CN114921502B (en) * | 2022-04-21 | 2023-10-20 | 东华大学 | Glutaric acid production method for feedback regulation and control of nitrogen source flow based on microorganism physiological parameters |
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