CN103725718A - Method for synthesizing acetoin and derivative thereof through biological method - Google Patents
Method for synthesizing acetoin and derivative thereof through biological method Download PDFInfo
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Abstract
The invention discloses a method for synthesizing acetoin and a derivative thereof through a biological method, which belongs to the technical field of the molecular biology. The method comprises the steps of introducing pyruvate decarboxylase genes and genes with acetoin enzyme activity into host bacteria to obtain recombination bacteria, producing the acetoin by fermenting the recombination bacteria, and further producing 2,3-butanediol on the basis of the acetoin. By adopting the method, the acetoin and the 2,3-butanediol are successfully generated by fermenting the recombined bacteria strain, and the problem that the yield of the acetoin and the 2,3-butanediol is influenced by the consumption of an intermediate product acetyl emulsion in the natural production process can be solved.
Description
Technical field
The present invention relates to a kind of method of synthetic acetoin, specifically intestinal bacteria are carried out to molecular biology transformation and make its synthetic acetoin, and at the enterprising one-step synthesis 2,3-butanediol in acetoin basis, belong to technical field of molecular biology.
Background technology
Acetoin (another name: methyl acetylcarbinol, 3-hydroxy-2-butanone) has strong cream, fat-like fragrance, has pleasant milk fragrance after high dilution, is mainly used in configuring essence, is important foodstuff additive and medicine synthesis material.Acetoin can be reacted by 2,3-dimethyl diketone acquisition under acidic conditions with zinc traditionally, or is prepared with fungi fermentations such as Aspergillus bacterium or Penicillium notatums by carbohydrate.2,3-butanediol is mainly as spices and organic synthesis reagent, or potential biofuel, can through the fermentation of Bacillus subtilus class, be obtained by carbohydrate.
From carbohydrate, though have report by the microorganisms producing acetoin of engineered mistake and the method for 2,3-butanediol, these methods are all based on a kind of natural anabolism path: two pyruvic acid of acetolactate synthase catalysis are condensed into acetylactis; The decarboxylation of acetolactate decarboxylase catalysis acetylactis generates acetoin; The reduction of acetoin reductase enzyme catalysis acetoin generates 2,3-butanediol.This natural approach is take acetylactis as crucial metabolic intermediate, but acetylactis is also used to synthesizing amino acid, terpene etc. in microbial metabolism, therefore can be consumed in a large number, thereby can affect the production of acetoin and 2,3-butanediol.
Summary of the invention
The invention provides a kind of synthetic acetoin method, by by Pyruvate Decarboxylase Gene, there is acetoin synthase activity gene, import Host Strains obtain recombinant bacterium, utilize recombinant bacterium fermentative production acetoin, further on acetoin basis, produce the method for 2,3-butanediol.
Technical solution of the present invention is as follows:
(1) clone Pyruvate Decarboxylase Gene and there is acetoin synthase activity gene;
(2) gene of step (1) gained is connected on plasmid vector, builds respectively the recombinant plasmid that contains Pyruvate Decarboxylase Gene and acetoin synthase gene;
(3) recombinant plasmid in step (2) is imported to Host Strains, obtain recombinant bacterium;
(4) utilize recombinant bacterium fermentative production acetoin in step (3).
The concrete steps of aforesaid method are as follows:
(1) clone respectively Pyruvate Decarboxylase Gene and there is acetoin synthase activity gene;
(2) by the gene of step (1) gained, Pyruvate Decarboxylase Gene connects pET28a plasmid, has acetoin synthase activity gene and connects pACYduet1 plasmid;
(3) two recombinant plasmids that step (2) obtained import in intestinal bacteria, obtain recombination bacillus coli;
(4) the recombination bacillus coli fermentative production acetoin of utilizing step (3) to obtain.
In the production of above-mentioned acetoin, in described Pyruvate Decarboxylase Gene, derive from zymomonas mobilis or acetone-butanol fusobacterium; Described to have acetoin synthase activity gene be acetoin dehydrogenase acoABCL, and pyruvic oxidase E1 subunit PDHA1 gene and LOC100516695 gene are any in acetolactate synthase ILV2 gene or YerE enzyme yerE gene.
According to aforesaid method, utilize the yerE genes produce acetoin of pyruvic carboxylase PDC gene and bacterium Yersinia pseudotuberculosis, concrete steps are as follows:
(1) clone respectively the pyruvic carboxylase PDC gene of zymomonas mobilis and the yerE gene of bacterium Yersinia pseudotuberculosis;
(2) described step (1) PDC gene is connected on pET28a plasmid, the novel plasmid pJXL65 obtaining, is connected to yerE gene on pACYduet1 plasmid, the novel plasmid pJXL63 obtaining;
(3) the plasmid vector pJXL65 Electroporation together with pJXL63 step (2) Suo Shu is entered in e. coli bl21 (DE3), obtain recombinant bacterium;
(4) utilize the recombinant bacterium fermentative production acetoin in step (3).
The preferred glucose of above-mentioned recombinant bacterium is fermenting raw materials production acetoin.
The present invention also provides a kind of method of synthetic 2,3-butanediol, is by Pyruvate Decarboxylase Gene, has acetoin synthase activity gene and have acetoin reductase activity gene, import Host Strains and obtain recombinant bacterium, utilize recombinant bacterium fermentative production 2,3-butanediol, key step is as follows:
(1) clone respectively Pyruvate Decarboxylase Gene, there is acetoin synthase activity gene and there is acetoin reductase activity gene;
(2) by have acetoin synthase activity gene, Pyruvate Decarboxylase Gene and acetoin reductase activity gene be connected respectively to can two plasmids compatible in same host cell on;
(3) step (2) recombinant plasmid transformed that obtains is entered to intestinal bacteria and obtain recombinant bacterium;
(4) utilize the recombinant bacterium fermentative production 2,3-butanediol in step (3).
The concrete steps of aforesaid method are as follows:
(1) clone respectively Pyruvate Decarboxylase Gene, there is acetoin synthase activity gene and there is acetoin reductase activity gene; Described Pyruvate Decarboxylase Gene derives from zymomonas mobilis or acetone-butanol fusobacterium; Described to have acetoin synthase activity gene be acetoin dehydrogenase acoABCL, and pyruvic oxidase E1 subunit PDHA1 gene and LOC100516695 gene are any in acetolactate synthase ILV2 gene or YerE enzyme yerE gene; It is described that to have acetoin reductase activity gene be any in 2,3-butanediol desaturase bdhA gene or alcoholdehydrogenase adh gene;
(2) will have acetoin synthase activity gene is connected to pACYduet1 plasmid and obtains plasmid pJXL63, step (1) gained Pyruvate Decarboxylase Gene is connected to pJXL63 plasmid and obtains recombinant plasmid pJXL78, by thering is acetoin reductase activity gene, be connected to the recombinant plasmid pJXL79 that pET28a plasmid vector obtains;
(3) step (2) the recombinant plasmid pJXL78 that obtains and pJXL79 are transformed into intestinal bacteria and obtain recombinant bacterium;
(4) utilize the recombinant bacterium fermentative production 2,3-butanediol in step (3).
According to aforesaid method, utilize the concrete steps of the synthetic 2,3-butanediol of pyruvic carboxylase PDC gene and 2,3-butanediol desaturase bdhA gene as follows:
(1) clone's pyruvic carboxylase PDC gene of fermentation single cell bacterium and the 2,3-butanediol desaturase bdhA gene of subtilis; (2) yerE gene is connected to the novel plasmid pJXL63 that pACYduet1 plasmid vector obtains, step (1) gained PDC gene is connected to pJXL63 plasmid and obtains recombinant plasmid pJXL78, bdhA gene is connected to the recombinant plasmid pJXL79 that pET28a plasmid vector obtains;
(3) step (2) the recombinant plasmid pJXL78 that obtains and pJXL79 Electroporation are entered in e. coli bl21 (DE3), obtain recombinant bacterium;
(4) utilize the recombinant bacterium fermentative production 2,3-butanediol in step (3).
The preferred glucose of above-mentioned recombinant bacterium is that fermenting raw materials is produced 2,3-butanediol.The present invention also provides for the method for biological process production acetoin and 2,3-butanediol and material.Specifically, the invention provides nucleic acid molecule, polypeptide, host cell and the method for the production of acetoin and 2,3-butanediol.The nucleic acid molecule of herein mentioning can be used for host cell to carry out genetic engineering modified, makes it have the ability of production acetoin and 2,3-butanediol.The polypeptide of herein mentioning can be used on production acetoin and 2,3-butanediol in cell-free system.The host cell of herein mentioning can be used on production acetoin and 2,3-butanediol in culture system.
The invention provides the cell with pyruvic carboxylase activity and/or acetoin synthase activity and/or methyl acetoin reductase activity, and produce the method for those products as described herein by cultivating these cells.Cell itself contains required enzymic activity as zymomonas mobilis, yeast in some embodiments.In other embodiments, the exogenous nucleic acid that cell contains encoding such enzymes.
In some embodiments, described cell also contains active these cells of diol dehydratase enzymic activity and/or alcoholdehydrogenase and 2,3-butanediol can be further converted to butanone and 2-butanols.
After the present invention successfully utilizes restructuring, strain fermentation generates acetoin and 2,3-butanediol, and having solved intermediate product acetylactis consumption in natural production ways affect the problem of acetoin and 2,3-butanediol production.
Accompanying drawing explanation
The structural formula of each compound of mentioning in Fig. 1 the present invention;
(1. acetylactis, 2. acetaldehyde, 3. pyruvic acid, 4. acetoin, 5.2,3-butyleneglycol).
The anabolism path schematic diagram of Fig. 2 biological process production acetoin;
(1. pyruvic carboxylase, 2. acetoin synthase).
Fig. 3 biological process is produced the anabolism path schematic diagram of 2,3-butanediol;
(1. pyruvic carboxylase, 2. acetoin synthase, 3. acetoin reductase enzyme).
The structural representation of Fig. 4 plasmid pJXL65.
The structural representation of Fig. 5 plasmid pJXL63.
The structural representation of Fig. 6 plasmid pJXL78.
The structural representation of Fig. 7 plasmid pJXL79.
The acetoin that Fig. 8 produces detects the TIC figure producing by gas chromatograph-mass spectrometer.
The acetoin that Fig. 9 produces detects the mass spectrum producing by gas chromatograph-mass spectrometer.
Embodiment
The path of biological process synthesizing methyl acetoin and derivative thereof has been described in Fig. 1-3: the decarboxylation of pyruvic carboxylase catalysis pyruvic acid generates acetaldehyde; A kind of enzyme catalysis acetaldehyde and pyruvic acid reaction with acetoin synthase activity generates acetoin; The reduction of acetoin reductase enzyme catalysis acetoin generates 2,3-butanediol.Here said decarboxylase, synthase, reductase activity are extensively present in various cells.Can utilize these enzymic activitys intrinsic in cell.Also can from other species, clone these enzymes be then transferred in cell and go.These enzymes can be also by the enzyme of transformation.This transformation can realize by mutagenesis screening or orthogenesis.
The multiple albumen take thiaminpyrophosphate as coenzyme it has been found that at present has the acetoin synthase activity shown in Fig. 1-3.Such as the E1 subunit of acetoin dehydrogenase, the E1 subunit of the pyruvic oxidase of animal, acetolactate synthase, transketolase, YerE enzyme.These albumen can be applied to the present invention.These albumen and their source of nucleic acid of encoding are exemplified below:
Table 1 has albumen and the gene thereof of acetoin synthase activity
The multiple protein it has been found that at present has the pyruvic carboxylase activity shown in Fig. 1-3.These albumen and their the nucleic acid source of encoding are exemplified below
Table 2 pyruvic carboxylase and gene thereof
The multiple protein it has been found that at present has the acetoin reductase activity shown in Fig. 1-3.These albumen and their the nucleic acid source of encoding are exemplified below:
Table 3 has albumen and the gene thereof of acetoin reductase activity
The nucleic acid of encoding such enzymes can be structured on suitable carrier such as pET28a, and pACYduet1 is upper, proceeds to cell.Also the enzymic activity that can utilize cell itself just to have, such as the 2,3-butanediol dehydrogenase activity of subtilis.Can be by the catalytic activity of the gene copy number increase enzyme of raising gene under latter event.The method that builds said these cells is all method conventional in biology; concrete steps can be with reference to Sambrook et al., Molecular Cloning:A Laboratory Manual, Third Ed.; Cold Spring Harbor Laboratory, New York (2001); And Ausubel et al., Current Protocols in Molecular Biology, John Wiley and Sons, Baltimore, Md. (1999).
The expression of enzyme is verified by traditional northren hybrid method.The ability of the products such as cells produce acetoin, 2,3-butanediol proves by detecting tunning.The detection of these products adopts gas-chromatography and mass-spectrometric technique.
By the PDC gene clone of zymomonas mobilis at pET28a(purchased from Novagen) between the NdeI and BglII site of plasmid vector, the novel plasmid obtaining is called pJXL65(Fig. 4).The pyruvic carboxylase encoding gene that in Fig. 4, Zm6PDC is zymomonas mobilis.By the yerE gene clone of bacterium Yersinia pseudotuberculosis at pACYduet1(purchased from Novagen) between the NdeI and KpnI restriction enzyme site of plasmid vector, the novel plasmid obtaining is called pJXL63(Fig. 5).PJXL65 Electroporation together with pJXL63 is entered in e. coli bl21 (DE3) (purchased from Invitrogen).The cell building is cultivated (sterilizing cooling rear both equal proportions are mixed for 0.5L water dissolution 10g sodium-chlor, 10g Trypsin powder and 5g yeast powder steam sterilizing, 0.5L water dissolution 20g glucose steam sterilizing) in 100ml LB dextrose culture-medium.Culture temperature is stabilized in 30 degrees Celsius.When Growth of Cells is to certain phase, normally index growth phase, adding IPTG(final concentration is 50mg/L) expression of induction exogenous enzyme, make cells produce acetoin, utilize gas chromatograph-mass spectrometer to detect synthetic acetoin (seeing Fig. 8,9).The peak that in Fig. 8, the peak of 7.049 points is acetoin, in Fig. 9, the molecular structure of ms fragment pattern and acetoin matches.The concentration of acetoin is 10.2g/L.
By the PDC gene clone of zymomonas mobilis, between the NcoI and BamHI restriction enzyme site of pJXL63 plasmid, the novel plasmid obtaining is called pJXL78(Fig. 6).By the bdhA gene clone of subtilis at pET28a(purchased from Novagen) between the NcoI and BamHI restriction enzyme site of plasmid vector, the novel plasmid obtaining is called pJXL79(Fig. 7).PJXL78 Electroporation together with pJXL79 is entered in e. coli bl21 (DE3) (purchased from Invitrogen).The cell building is cultivated (sterilizing cooling rear both equal proportions are mixed for 0.5L water dissolution 10g sodium-chlor, 10g Trypsin powder and 5g yeast powder steam sterilizing, 0.5L water dissolution 20g glucose steam sterilizing) in 100ml LB dextrose culture-medium.Culture temperature is stabilized in 30 degrees Celsius.When Growth of Cells is to certain phase, normally index growth phase, adding IPTG(final concentration is 50mg/L) expression of induction exogenous enzyme, make cells produce 2,3-butanediol.The concentration of 2,3-butanediol is 9.5g/L.
Claims (10)
1. a method for the synthetic acetoin of biological process, is characterized in that, by Pyruvate Decarboxylase Gene, have acetoin synthase activity gene, imports Host Strains and obtains recombinant bacterium, utilizes recombinant bacterium fermentative production acetoin.
2. method according to claim 1, is characterized in that, step is as follows:
(1) clone Pyruvate Decarboxylase Gene and there is acetoin synthase activity gene;
(2) gene of step (1) gained is connected on plasmid vector, builds respectively the recombinant plasmid that contains Pyruvate Decarboxylase Gene and acetoin synthase gene;
(3) recombinant plasmid in step (2) is imported to intestinal bacteria, obtain recombination bacillus coli;
(4) the recombination bacillus coli fermentative production acetoin of utilizing step (3) to obtain.
3. method according to claim 2, is characterized in that, concrete steps are as follows:
(1) clone respectively Pyruvate Decarboxylase Gene and there is acetoin synthase activity gene;
(2) by the gene of step (1) gained, Pyruvate Decarboxylase Gene is connected on pET28a plasmid, makes recombinant plasmid pJXL65, has acetoin synthase activity gene and is connected on pACYduet1 plasmid, makes recombinant plasmid pJXL63;
(3) two recombinant plasmids that step (2) obtained import in intestinal bacteria, obtain recombination bacillus coli;
(4) the recombination bacillus coli fermentative production acetoin of utilizing step (3) to obtain.
4. according to either method described in claim 1-3, it is characterized in that, described Pyruvate Decarboxylase Gene derives from motion fermentation list
Born of the same parents bacterium or acetone-butanol fusobacterium.
5. according to either method described in claim 1-3, it is characterized in that, it is described that to have acetoin synthase activity gene be acetoin dehydrogenase acoABCL gene, pyruvic oxidase E1 subunit PDHA1 gene and LOC100516695 gene, any in acetolactate synthase ILV2 gene or YerE enzyme yerE gene.
6. according to either method described in claim 1-3, it is characterized in that, concrete steps are as follows:
(1) clone respectively the Pyruvate Decarboxylase Gene PDC gene of zymomonas mobilis and the yerE gene of bacterium Yersinia pseudotuberculosis;
(2) described step (1) PDC gene is connected on pET28a plasmid, the novel plasmid pJXL65 obtaining, is connected to yerE gene on pACYduet1 plasmid vector, the novel plasmid pJXL63 obtaining;
(3) the plasmid vector pJXL65 Electroporation together with pJXL63 step (2) Suo Shu is entered in e. coli bl21 (DE3), obtain recombinant bacterium;
(4) utilize the recombinant bacterium fermentative production acetoin in step (3).
7. a method for synthetic 2,3-butanediol, is by Pyruvate Decarboxylase Gene, has acetoin synthase activity gene and have acetoin reductase activity gene, imports Host Strains and obtains recombinant bacterium, utilizes recombinant bacterium fermentative production 2,3-butanediol.
8. method according to claim 7, is characterized in that, concrete steps are as follows:
(1) clone respectively Pyruvate Decarboxylase Gene, there is acetoin synthase activity gene and there is acetoin reductase activity gene;
(2) by have acetoin synthase activity gene, Pyruvate Decarboxylase Gene and acetoin reductase activity gene be connected respectively to can two plasmids compatible in same host cell on;
(3) step (2) recombinant plasmid transformed that obtains is entered to intestinal bacteria and obtain recombinant bacterium;
(4) utilize the recombinant bacterium fermentative production 2,3-butanediol in step (3).
9. method according to claim 7, is characterized in that, concrete steps are as follows:
(1) clone respectively Pyruvate Decarboxylase Gene, there is acetoin synthase activity gene and there is acetoin reductase activity gene; Described Pyruvate Decarboxylase Gene derives from zymomonas mobilis or acetone-butanol fusobacterium; Described to have acetoin synthase activity gene be acetoin dehydrogenase acoABCL gene, and pyruvic oxidase E1 subunit PDHA1 gene and LOC100516695 gene are any in acetolactate synthase ILV2 gene or YerE enzyme yerE gene; It is described that to have acetoin reductase activity gene be any in 2,3-butanediol desaturase bdhA gene or alcoholdehydrogenase adh gene;
(2) will have acetoin synthase activity gene is connected to pACYduet1 plasmid and obtains recombinant plasmid pJXL63, step (1) gained Pyruvate Decarboxylase Gene is connected to pJXL63 plasmid and obtains recombinant plasmid pJXL78, by thering is acetoin reductase activity gene, be connected to the recombinant plasmid pJXL79 that pET28a plasmid obtains;
(3) step (2) the recombinant plasmid pJXL78 that obtains and pJXL79 are transformed into intestinal bacteria and obtain recombinant bacterium;
(4) utilize the recombinant bacterium fermentative production 2,3-butanediol in step (3).
10. method according to claim 7, is characterized in that, concrete steps are as follows:
(1) clone's pyruvic carboxylase PDC gene of fermentation single cell bacterium and the 2,3-butanediol desaturase bdhA gene of subtilis;
(2) yerE gene is connected to pACYduet1 plasmid vector and obtains recombinant plasmid pJXL63, step (1) gained PDC gene is connected to pJXL63 plasmid and obtains recombinant plasmid pJXL78, bdhA gene is connected to the recombinant plasmid pJXL79 that pET28a plasmid obtains;
(3) step (2) the recombinant plasmid pJXL78 that obtains and pJXL79 Electroporation are entered in e. coli bl21 (DE3), obtain recombinant bacterium;
(4) utilize the recombinant bacterium fermentative production 2,3-butanediol in step (3).
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Cited By (4)
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| CN105505849A (en) * | 2016-01-22 | 2016-04-20 | 南京工业大学 | Genetic engineering bacterium for co-production of butanol and 2, 3-butanediol as well as construction method and application thereof |
| CN106967741A (en) * | 2017-04-03 | 2017-07-21 | 天津大学 | A kind of external enzyme reaction production L（+）The method of 3-hydroxy-2-butanone |
| CN107636151A (en) * | 2015-05-22 | 2018-01-26 | 杜邦营养生物科学有限公司 | Acetolactate decarboxylase |
| CN107653259A (en) * | 2017-10-18 | 2018-02-02 | 天津大学 | A kind of method of external enzyme reaction production D () 3-hydroxy-2-butanone |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107636151A (en) * | 2015-05-22 | 2018-01-26 | 杜邦营养生物科学有限公司 | Acetolactate decarboxylase |
| CN107636151B (en) * | 2015-05-22 | 2023-04-04 | 杜邦营养生物科学有限公司 | Acetolactate decarboxylase |
| CN105505849A (en) * | 2016-01-22 | 2016-04-20 | 南京工业大学 | Genetic engineering bacterium for co-production of butanol and 2, 3-butanediol as well as construction method and application thereof |
| CN105505849B (en) * | 2016-01-22 | 2019-09-20 | 南京工业大学 | Genetic engineering bacterium for co-production of butanol and 2,3-butanediol as well as construction method and application thereof |
| CN106967741A (en) * | 2017-04-03 | 2017-07-21 | 天津大学 | A kind of external enzyme reaction production L（+）The method of 3-hydroxy-2-butanone |
| CN106967741B (en) * | 2017-04-03 | 2020-02-21 | 天津大学 | Method for producing L (+) -acetoin through in vitro enzyme reaction |
| CN107653259A (en) * | 2017-10-18 | 2018-02-02 | 天津大学 | A kind of method of external enzyme reaction production D () 3-hydroxy-2-butanone |
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Inventor after: Liu Wei Inventor after: Xian Mo Inventor after: Jiang Xinglin Inventor after: Xu Xin Inventor after: Liu Hui Inventor before: Xian Mo Inventor before: Jiang Xinglin Inventor before: Liu Wei Inventor before: Xu Xin Inventor before: Liu Hui |