CN103725718B - 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 for synthesizing 3-hydroxy-2-butanone, molecular biology transformation specifically is carried out to Escherichia coli
Make its synthesis 3-hydroxy-2-butanone, and the further synthesis 2,3-butanediol on the basis of 3-hydroxy-2-butanone, belong to technical field of molecular biology.
Background technology
3-hydroxy-2-butanone（Alias:Methyl vinyl methyl alcohol, 3- hydroxy-2-butanones）With strong cream, fat-like fragrance, height
There is pleasant milk fragrance after dilution, be mainly used in configuring essence, be important food additives and pharmaceutical synthesis raw material.Pass
3-hydroxy-2-butanone can in acid condition react acquisition by 2,3- diacetyl and zinc on system, or by carbohydrate with aspergillus bacterium or
It is prepared by the fungi fermentations such as Penicillium notatum.2,3-butanediol is mainly used as spices and organic synthesis reagent, or potential bio-fuel,
Can be fermented through hay bacillus class by carbohydrate and obtained.
From carbohydrate, though the method for the micro-organisms 3-hydroxy-2-butanone and 2,3-butanediol for passing through engineered mistake
Have been reported that, but these methods are all based on a kind of natural anabolism path：Acetolactate synthase is catalyzed two pyruvic acid condensations
Into acetolactic acid；Acetolactate decarboxylase catalysis acetolactic acid decarboxylation generation 3-hydroxy-2-butanone；3-hydroxy-2-butanone reduction enzymatic 3-hydroxy-2-butanone is also
It is primary into 2,3- butanediols.This natural route is with acetolactic acid as key metabolic intermediates, but acetolactic acid is in microorganism generation
Also it is used for synthesizing amino acid, terpene etc. in thanking, therefore can be largely consumed, so as to 3-hydroxy-2-butanone and 2,3-butanediol can be influenceed
Production.
The content of the invention
The present invention provides a kind of synthesis 3-hydroxy-2-butanone method, is lived by by Pyruvate Decarboxylase Gene, with 3-hydroxy-2-butanone synthase
Property gene, import Host Strains and obtain recombinant bacterium, using recombinant bacterium fermenting and producing 3-hydroxy-2-butanone, further produced on the basis of 3-hydroxy-2-butanone
The method of 2,3- butanediols.
Technical solution of the present invention is as follows：
（1）Clone Pyruvate Decarboxylase Gene and with 3-hydroxy-2-butanone synthase activity gene；
（2）By step（1）The gene of gained is connected on plasmid vector, build respectively containing Pyruvate Decarboxylase Gene and
The recombinant plasmid of 3-hydroxy-2-butanone synthase gene；
（3）By step（2）In recombinant plasmid import Host Strains, obtain recombinant bacterium；
（4）Using step（3）Middle recombinant bacterium fermenting and producing 3-hydroxy-2-butanone.
The above method is comprised the following steps that：
（1）Pyruvate Decarboxylase Gene is cloned respectively and with 3-hydroxy-2-butanone synthase activity gene；
（2）By step（1）The gene of gained, Pyruvate Decarboxylase Gene connection pET28a plasmids, with 3-hydroxy-2-butanone synthase
Active gene connects pACYduet1 plasmids；
（3）By step（2）Two recombinant plasmids for obtaining are imported into Escherichia coli, obtain recombination bacillus coli；
（4）Using step（3）The recombination bacillus coli fermenting and producing 3-hydroxy-2-butanone for obtaining.
In the production of above-mentioned 3-hydroxy-2-butanone zymomonas mobilis or acetone fourth are derived from the Pyruvate Decarboxylase Gene
Alcohol Fusobacterium；Described is acetoin dehydrogenase acoABCL, pyruvic dehydrogenase E1 subunits with 3-hydroxy-2-butanone synthase activity gene
In PDHA1 genes and LOC100516695 genes, acetolactate synthase ILV2 genes or YerE enzyme yerE genes any.
According to the above method, using pyruvate decarboxylase PDC genes and bacterium Yersinia pseudotuberculosis
YerE genes production 3-hydroxy-2-butanone, comprise the following steps that：
（1）The pyruvate decarboxylase PDC genes and bacterium Yersinia of zymomonas mobilis are cloned respectively
The yerE genes of pseudotuberculosis；
（2）By step（1）The PDC genes are connected on pET28a plasmids, the novel plasmid pJXL65 for obtaining, by yerE bases
Because being connected on pACYduet1 plasmids, the novel plasmid pJXL63 for obtaining；
（3）By step（2）Electroporation enters e. coli bl21 to described plasmid vector pJXL65 and pJXL63 together
（DE3）In, obtain recombinant bacterium；
（4）Using step（3）In recombinant bacterium fermenting and producing 3-hydroxy-2-butanone.
The above-mentioned preferred glucose of recombinant bacterium is that fermenting raw materials produce 3-hydroxy-2-butanone.
It is by Pyruvate Decarboxylase Gene, with second idol present invention also offers a kind of method for synthesizing 2,3-butanediol
Relation by marriage synthase activity gene and with 3-hydroxy-2-butanone reductase activity gene, imports Host Strains and obtains recombinant bacterium, is fermented using recombinant bacterium
Production 2,3-butanediol, key step is as follows：
（1）Pyruvate Decarboxylase Gene is cloned respectively, with 3-hydroxy-2-butanone synthase activity gene and with 3-hydroxy-2-butanone reductase
Active gene；
（2）Will be with 3-hydroxy-2-butanone synthase activity gene, Pyruvate Decarboxylase Gene and 3-hydroxy-2-butanone reductase activity gene point
Be not connected to can be compatible in same host cell two plasmids on；
（3）By step（2）Obtained recombinant plasmid transformed enters Escherichia coli and obtains recombinant bacterium；
（4）Using step（3）In recombinant bacterium fermenting and producing 2,3- butanediols.
The above method is comprised the following steps that：
（1）Pyruvate Decarboxylase Gene is cloned respectively, with 3-hydroxy-2-butanone synthase activity gene and with 3-hydroxy-2-butanone reductase
Active gene；The Pyruvate Decarboxylase Gene derives from zymomonas mobilis or Clostridium acetobutylicum；It is described with second
Acyloin synthase activity gene be acetoin dehydrogenase acoABCL, pyruvic dehydrogenase E1 subunit PDHA1 genes and
In LOC100516695 genes, acetolactate synthase ILV2 genes or YerE enzyme yerE genes any；It is described with second idol
Relation by marriage reductase activity gene is any in 2,3- butanediol dehydrogenase bdhA genes or alcohol dehydrogenase adh genes；
（2）PACYduet1 plasmids will be connected to 3-hydroxy-2-butanone synthase activity gene and obtain plasmid pJXL63, by step
（1）Gained Pyruvate Decarboxylase Gene is connected to pJXL63 plasmids and obtains recombinant plasmid pJXL78, will be with 3-hydroxy-2-butanone reductase
Active gene is connected to the recombinant plasmid pJXL79 that pET28a plasmid vectors are obtained；
（3）By step（2）Obtained recombinant plasmid pJXL78 and pJXL79 is transformed into Escherichia coli and obtains recombinant bacterium；
（4）Using step（3）In recombinant bacterium fermenting and producing 2,3- butanediols.
According to the above method, using pyruvate decarboxylase PDC genes and 2,3-butanediol dehydrogenase bdhA gene chemical synthesis 2,
3- butanediols are comprised the following steps that：
（1）Clone the pyruvate decarboxylase PDC genes of fermentation single cell bacterium and the 2,3- butanediol dehydrogenations of bacillus subtilis
Enzyme bdhA genes；（2）YerE genes are connected to the novel plasmid pJXL63 that pACYduet1 plasmid vectors are obtained, by step（1）Institute
PDC genes are connected to pJXL63 plasmids and obtain recombinant plasmid pJXL78, bdhA genes are connected into pET28a plasmid vectors obtains
The recombinant plasmid pJXL79 for arriving；
（3）By step（2）Obtained recombinant plasmid pJXL78 and pJXL79 Electroporations enter e. coli bl21（DE3）In,
Obtain recombinant bacterium；
（4）Using step（3）In recombinant bacterium fermenting and producing 2,3- butanediols.
The above-mentioned preferred glucose of recombinant bacterium is that fermenting raw materials produce 2,3- butanediols.Present invention also offers for bioanalysis
The method and material of production 3-hydroxy-2-butanone and 2,3-butanediol.Specifically, the invention provides for producing 3-hydroxy-2-butanone and 2,3-
The nucleic acid molecules of butanediol, polypeptide, host cell and method.Referring herein to nucleic acid molecules can be used to carry out base to host cell
Because engineered, the ability of production 3-hydroxy-2-butanone and 2,3-butanediol is made it have.Referring herein to polypeptide can be used on acellular body
3-hydroxy-2-butanone and 2,3-butanediol are produced in system.Referring herein to host cell can be used on 3-hydroxy-2-butanone and 2,3- are produced in cultivating system
Butanediol.
The invention provides with Pyruvate decarboxylase activity and/or 3-hydroxy-2-butanone synthase activity and/or methyl 3-hydroxy-2-butanone also
The cell of original enzyme activity, and the method for producing product as those described herein by cultivating these cells.In some realities
Cell contains required enzymatic activity such as zymomonas mobilis, saccharomycete in itself in applying scheme.In other embodiments, cell
Exogenous nucleic acid containing encoding such enzymes.
In some embodiments, described cell also containing diol dehydratase enzymatic activity and/or alcohol dehydrogenase activity these
2,3- butanediols can be further converted to butanone and 2- butanol by cell.
The present invention successfully using strain fermentation generation 3-hydroxy-2-butanone and 2,3-butanediol after restructuring, solves natural production ways
Middle intermediate product acetolactic acid consumption influence 3-hydroxy-2-butanone and the problem of 2,3- butanediols production.
Brief description of the drawings
The structural formula of each compound mentioned in Fig. 1 present invention；
（1. acetolactic acid, 2. acetaldehyde, 3. pyruvic acid, 4. 3-hydroxy-2-butanone, 5.2,3- butanediols）.
Fig. 2 bioanalysises produce the anabolism path schematic diagram of 3-hydroxy-2-butanone；
（1. pyruvate decarboxylase, 2. 3-hydroxy-2-butanone synthase）.
Fig. 3 bioanalysises produce the anabolism path schematic diagram of 2,3- butanediols；
（1. pyruvate decarboxylase, 2. 3-hydroxy-2-butanone synthase, 3. 3-hydroxy-2-butanone reductase）.
The structural representation of Fig. 4 plasmids pJXL65.
The structural representation of Fig. 5 plasmids pJXL63.
The structural representation of Fig. 6 plasmids pJXL78.
The structural representation of Fig. 7 plasmids pJXL79.
The 3-hydroxy-2-butanone that Fig. 8 is produced GC-MS detects that the TIC for producing schemes.
The 3-hydroxy-2-butanone that Fig. 9 is produced detects the mass spectrogram for producing with GC-MS.
Specific embodiment
Fig. 1-3 describes the path of bioanalysis synthesizing methyl 3-hydroxy-2-butanone and its derivative：Pyruvate decarboxylation enzymatic acetone
Acid decarboxylation generates acetaldehyde；A kind of enzymatic acetaldehyde and acetone acid reaction generation 3-hydroxy-2-butanone with 3-hydroxy-2-butanone synthase activity；Second idol
Relation by marriage reduction enzymatic 3-hydroxy-2-butanone reduction generation 2,3- butanediols.Decarboxylase mentioned here, synthase, reductase activity are widely present
In various cells.Can be using these enzymatic activitys intrinsic in cell.These enzymes can also be cloned from other species right
After be transferred in cell.These enzymes can also be the enzyme by transforming.This transformation can by mutagenesis screening or orient into
Change to realize.
At present it has been found that various albumen with b1thiaminpyrophosphate as coenzyme there is second idol shown in Fig. 1-3
Relation by marriage synthase activity.The E1 subunits of such as acetoin dehydrogenase, the E1 subunits of the pyruvic dehydrogenase of animal, acetolactate synthase,
Transketolase, YerE enzymes.These albumen can be applied to the present invention.These albumen and encode their nucleic acid source citing such as
Under：
Table 1 has the albumen and its gene of 3-hydroxy-2-butanone synthase activity
At present it has been found that multiple protein there is Pyruvate decarboxylase activity shown in Fig. 1-3.These albumen and
Their nucleic acid source is encoded to be exemplified below
The pyruvate decarboxylase of table 2 and its gene
At present it has been found that multiple protein there is 3-hydroxy-2-butanone reductase activity shown in Fig. 1-3.These albumen and
Their nucleic acid source is encoded to be exemplified below：
Table 3 has the albumen and its gene of 3-hydroxy-2-butanone reductase activity
The nucleic acid of encoding such enzymes can build the such as pET28a on suitable carrier, on pACYduet1, be transferred to thin
Born of the same parents.The enzymatic activity that cell can also be utilized inherently to have, such as the 2,3-butanediol dehydrogenase activity of bacillus subtilis.Rear
Can increase the catalysis activity of enzyme by improving the copy number of gene in the case of a kind of.Build the method for these described cells all
It is the method commonly used in biology, specific steps can refer 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 methods.The products such as cell production 3-hydroxy-2-butanone, 2,3- butanediols
Ability is proved by detecting tunning.The detection of these products uses gas-chromatography and mass-spectrometric technique.
Embodiment 1
By the PDC gene clonings of zymomonas mobilis in pET28a（Purchased from Novagen）The NdeI of plasmid vector and
Between BglII sites, the novel plasmid for obtaining referred to as pJXL65（Fig. 4）.Zm6PDC is the pyruvic acid of zymomonas mobilis in Fig. 4
Decarboxylase encoding gene.By the yerE gene clonings of bacterium Yersinia pseudotuberculosis in pACYduet1（Purchase
From Novagen）Between NdeI the and KpnI restriction enzyme sites of plasmid vector, the novel plasmid for obtaining referred to as pJXL63（Fig. 5）.Will
Electroporation enters e. coli bl21 together for pJXL65 and pJXL63（DE3）（Purchased from Invitrogen）In.The cell for building,
Cultivated in 100ml LB dextrose culture-mediums（0.5L water dissolves 10g sodium chloride, 10g tryptoses powder and 5g dusty yeast steam go out
Bacterium, 0.5L water dissolves 20g glucose steam sterilizings, both equal proportion mixing after sterilizing and cooling down）.Cultivation temperature stabilization is taken the photograph 30
Family name's degree.When cell growth to certain phase, typically exponential growth, IPTG is added（Final concentration of 50mg/L）Induction external source
The expression of enzyme, makes cell produce 3-hydroxy-2-butanone, using the 3-hydroxy-2-butanone of GC-MS detection synthesis（See Fig. 8,9）.Fig. 8
In 7.049 points peak for 3-hydroxy-2-butanone peak, ms fragment pattern matches with the molecular structure of 3-hydroxy-2-butanone in Fig. 9.3-hydroxy-2-butanone
Concentration is 10.2g/L.
Embodiment 2
By the PDC gene clonings of zymomonas mobilis between NcoI the and BamHI restriction enzyme sites of pJXL63 plasmids, obtain
The novel plasmid for arriving referred to as pJXL78（Fig. 6）.By the bdhA gene clonings of bacillus subtilis in pET28a（Purchased from Novagen）Matter
Between NcoI the and BamHI restriction enzyme sites of grain carrier, the novel plasmid for obtaining referred to as pJXL79（Fig. 7）.By pJXL78 and pJXL79
Electroporation enters e. coli bl21 together（DE3）（Purchased from Invitrogen）In.The cell for building, in 100ml LB grapes
Cultivated in sugar culture-medium（0.5L water dissolves 10g sodium chloride, 10g tryptoses powder and 5g dusty yeast steam sterilizings, 0.5L water dissolves
20g glucose steam sterilizings, both equal proportion mixing after sterilizing and cooling down）.Cultivation temperature stabilization is at 30 degrees Celsius.When cell life
Certain phase, typically exponential growth are grown to, IPTG is added（Final concentration of 50mg/L）The expression of exogenous enzymes is induced, is made thin
Born of the same parents produce 2,3- butanediols.The concentration of 2,3- butanediols is 9.5g/L.
Claims (6)
1. a kind of method that bioanalysis synthesizes 3-hydroxy-2-butanone, it is characterised in that step is as follows：
(1) Pyruvate Decarboxylase Gene PDC genes and YerE enzyme yerE genes are cloned respectively；
(2) gene obtained by step (1) is connected on plasmid vector, builds contain Pyruvate Decarboxylase Gene and second idol respectively
The recombinant plasmid of relation by marriage synthase gene；
(3) recombinant plasmid in step (2) is imported into Escherichia coli, obtains recombination bacillus coli；
(4) the recombination bacillus coli fermenting and producing 3-hydroxy-2-butanone obtained using step (3).
2. method according to claim 1, it is characterised in that comprise the following steps that：
(1) Pyruvate Decarboxylase Gene PDC genes and YerE enzyme yerE genes are cloned respectively；
(2) by the gene obtained by step (1), Pyruvate Decarboxylase Gene is connected on pET28a plasmids, is made recombinant plasmid
PJXL65, is connected on pACYduet1 plasmids with 3-hydroxy-2-butanone synthase activity gene, is made recombinant plasmid pJXL63；
(3) two recombinant plasmids that step (2) is obtained are imported into Escherichia coli, obtains recombination bacillus coli；
(4) the recombination bacillus coli fermenting and producing 3-hydroxy-2-butanone obtained using step (3).
3. the either method according to claim 1-2, it is characterised in that the Pyruvate Decarboxylase Gene is sent out from motion
Ferment monad or Clostridium acetobutylicum.
4. the either method according to claim 1-2, it is characterised in that comprise the following steps that：
(1) the Pyruvate Decarboxylase Gene PDC genes and bacterium Yersinia of zymomonas mobilis are cloned respectively
The yerE genes of pseudotuberculosis；
(2) step (1) the PDC genes are connected on pET28a plasmids, the novel plasmid pJXL65 for obtaining, yerE genes is connected
It is connected on pACYduet1 plasmid vectors, the novel plasmid pJXL63 for obtaining；
(3) the plasmid vector pJXL65 and pJXL63 described in step (2) together Electroporation are entered into e. coli bl21 (DE3)
In, obtain recombinant bacterium；
(4) using the recombinant bacterium fermenting and producing 3-hydroxy-2-butanone in step (3).
5. it is a kind of synthesize 2,3-butanediol method, it is characterised in that comprise the following steps that：
(1) pyruvate decarboxylase PDC genes, YerE enzyme yerE genes and 2,3-butanediol dehydrogenase bdhA genes are cloned respectively；
(2) by pyruvate decarboxylase PDC genes, YerE enzyme yerE genes and 2,3-butanediol dehydrogenase bdhA genes are connected respectively
To can be compatible in same host cell two plasmids on；
(3) step (2) is obtained into recombinant plasmid transformed enter Escherichia coli and obtain recombinant bacterium；
(4) using the recombinant bacterium fermenting and producing 2,3- butanediols in step (3).
6. method according to claim 5, it is characterised in that comprise the following steps that：
(1) the 2,3- butanediol dehydrogenases of the pyruvate decarboxylase PDC genes of clone's fermentation single cell bacterium and bacillus subtilis
BdhA genes；
(2) yerE genes are connected to pACYduet1 plasmid vectors and obtain recombinant plasmid pJXL63, by step (1) gained PDC bases
Recombinant plasmid pJXL78 is obtained because being connected to pJXL63 plasmids, bdhA genes are connected to the recombinant plasmid that pET28a plasmids are obtained
pJXL79；
(3) step (2) is obtained during recombinant plasmid pJXL78 and pJXL79 Electroporation enters e. coli bl21 (DE3), is obtained
Recombinant bacterium；
(4) using the recombinant bacterium fermenting and producing 2,3- butanediols in step (3).
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| 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 |
| CN106967741B (en) * | 2017-04-03 | 2020-02-21 | 天津大学 | Method for producing L (+) -acetoin through in vitro enzyme reaction |
| CN107653259B (en) * | 2017-10-18 | 2018-07-13 | 天津大学 | A kind of method of external enzyme reaction production D- (-) -3-hydroxy-2-butanone |
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