CN102876737A - Method for catalyzing and synthetising enzyme of D-benzene lactic acid - Google Patents
Method for catalyzing and synthetising enzyme of D-benzene lactic acid Download PDFInfo
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Abstract
The invention relates to a method for catalyzing and synthetising enzyme of D-benzene lactic acid. The method comprises the steps as follows: under the condition that reduced coenzyme NADH exists, phenylpyruvic acid is catalyzed by D-lactic acid dehydrogenase to carry out a hydrogenation reduction reaction so as to generate the D-benzene lactic acid; at the beginning of the reaction, in a reacting system, the concentration of phenylpyruvic acid is 1 to 1,000 mmol/L, the concentration of enzymatic activity of the D-lactic acid dehydrogenase is 0.1 to 100 U/L, and the concentration of the reduced coenzyme NADH is 0.01 to 100 mmol/L. Especially, formate dehydrogenase and sodium formate are further added in the reacting system after the hydrogenation reduction, at the beginning of the reaction, the concentration of the enzymatic activity of the formate dehydrogenase is 0.1 to 100 U/L, the concentration of the sodium formate is 1 to 1,000mmol/L, the temperature of the hydrogenation reduction reaction is 20 to 70 DEG C, the pH value in the reacting system is 3.0 to 9.0, and the reacting time is 0.5 to 10 h. The method has the advantages of high efficiency and low cost.
Description
Technical field
The present invention relates to a kind of synthetic method of D-phenyllactic acid, particularly the method for the synthetic D-phenyllactic acid of a kind of enzyme catalysis.
Background technology
Phenyllactic acid (Phenyllactic acid, PLA), namely PLA also claims PLA, is a kind of new type natural antibacterial substance of found while anti-bacteria and fungi in cheese first.Phenyllactic acid can suppress multiple food-borne pathogens, such as pathogenic colon bacillus (Escherichia coli O157:H7), streptococcus aureus (Staphylococcus aureus), Listeria monocytogenes (Listeria monocytogenes) etc.; Particularly the fungi that causes food spoilage is comprised that toxogenic fungi has the restraining effect of wide spectrum, its bacteriostatic activity is better than common Chemical Preservative, has become one of effective marker of milk-acid bacteria fungal resistance (Int J Food Microbiol 40:177-183; J Food Prot61:1281-1285; Appl Environ Microbiol 66:4084-4090).Compare with biological preservatives such as Nisin, tennecetins, phenyllactic acid has wider antimicrobial spectrum, can suppress simultaneously gram-positive microorganism, Gram-negative bacteria and fungi.Under 20PPm addition condition, fungus and bacterium is all reached good inhibition.In addition, phenyllactic acid also have solvability good, be easy in food system, spread; Stability is high, have broad pH scope and thermostability.Simultaneously, phenyllactic acid is a kind of natural bacteriostatic material, and is nontoxic to the humans and animals cell; Can be synthetic by lactic acid bacteria biological, and milk-acid bacteria is the microorganism that is known as safety (GRAS), is widely used in food-processing, preservation, has good food safety.Therefore, phenyllactic acid has the great market space in the antibacterial sanitas of high-efficiency broad spectrum biological food.Phenyllactic acid has D-phenyllactic acid and two kinds of configurations of L-phenyllactic acid, has to report a little higher than L-phenyllactic acid of bacteriostasis (Appl Environ Microbiol 64:800-803) of D-phenyllactic acid.
Biosynthesizing D-phenyllactic acid comprises the methods such as lactobacillus-fermented or enzyme catalysis, because in the synthetic D-phenyllactic acid process of lactobacillus-fermented, tunning is especially complicated, organic acid is various, the separation and purification that is unfavorable for the D-phenyllactic acid, and the synthetic D-phenyllactic acid of enzyme process does not have by product, so enzyme process is synthetic has certain advantage.Enzyme process synthesizes the D-phenyllactic acid, normally utilizes D-lactic acid dehydrogenase catalytic substrate phenyl-pyruvic acid hydrogenating reduction to synthesize the D-phenyllactic acid.This hydrogenating reduction process need reduced coenzyme NADH, this coenzyme is expensive, and in catalytic reaction process along with the hydrogenating reduction of phenyl-pyruvic acid, this coenzyme is oxidized to oxidized coenzyme NAD; Depleted when reduced coenzyme, this enzymic catalytic reaction can be owing to there not being electron donor to stop.Therefore, if in D-phenyllactic acid enzyme process building-up process, in time utilize another kind of catalyzed reaction to make the continuous circulating reduction of oxidized coenzyme NAD become reduced coenzyme NADH, then can make D-phenyllactic acid biosynthesizing efficient Effective Raise, this is that D-phenyllactic acid enzyme process synthetic technology does not set foot in so far, but is a kind of high efficiency technical of important research trend.
Summary of the invention
Technical problem to be solved by this invention is to overcome the deficiencies in the prior art, and a kind of enzymatic synthesis method of improved D-phenyllactic acid is provided, and the method combined coefficient is high, and cost is low.
For solving above technical problem, the present invention takes following technical scheme:
A kind of enzymatic synthesis method of D-phenyllactic acid, it makes phenyl-pyruvic acid that hydrogenation reduction generation D-phenyllactic acid occur under the D-lactic acid dehydrogenase catalysis and in the presence of the reduced coenzyme NADH, in the reaction system when reacting initial, the concentration of phenyl-pyruvic acid is 1～1000mmol/L, the concentration of enzymatic activity of D-lactic acid dehydrogenase is 0.1～100U/L, the concentration of reducibility coenzyme NADH is 0.01～100mmol/L, particularly, in the reaction system of hydrogenation reduction, also add hydrogenlyase and sodium formiate are arranged, when reacting initial, the concentration of enzymatic activity of hydrogenlyase is 0.1～100U/L, the concentration of sodium formiate is 1～1000mmol/L, the temperature of hydrogenation reduction is 20 ℃～70 ℃, the pH of reaction system is 3.0～9.0, and the reaction times is 0.5～10h.
According to a preferred aspect of the present invention, the temperature of described hydrogenation reduction is 30 ℃～60 ℃, more preferably 40 ℃～50 ℃.The pH of described reaction system is preferably 3～7, and more preferably 5～6.Under this temperature and pH condition, the described reaction times is preferably 0.5～2 hour.More preferably 0.75～1.5 hour.
According to a further preferred aspect of the invention, in the reaction system when reacting initial, the concentration of phenyl-pyruvic acid is 1～100mmol/L, the D-lactic acid dehydrogenase concentration of enzymatic activity is 1～100U/L, the concentration of reducibility coenzyme NADH is 0.1～10mmol/L, the concentration of enzymatic activity of hydrogenlyase is 1～100U/L, and the concentration of sodium formiate is 1～100mmol/L.More preferably, the concentration of phenyl-pyruvic acid is 1～50mmol/L, and the D-lactic acid dehydrogenase concentration of enzymatic activity is 1～50U/L, and the concentration of reducibility coenzyme NADH is 0.1～2mmol/L, the concentration of enzymatic activity of hydrogenlyase is 1～50U/L, and the concentration of sodium formiate is 1～50mmol/L.
According to a concrete aspect of the present invention, the gene source of described D-lactic acid dehydrogenase is in Pediococcus pentosaceus ATCC 25745 (gene library is numbered GeneID:4417836), and the gene source of hydrogenlyase is in Ogataea parapolymorpha DL-1 (gene library is numbered GI:320581066).
Because the utilization of technique scheme, the present invention compared with prior art has following advantages and effect:
The present invention synthesizes formic acid/hydrogenlyase system first Application in the enzyme catalysis system of phenyllactic acid in D-lactic acid dehydrogenase catalysis phenyl-pyruvic acid, reduced coenzyme NADH in the enzyme catalysis system is regenerated, realize the efficiently synthetic D-phenyllactic acid of D-lactic acid dehydrogenase catalysis phenyl-pyruvic acid, increased substantially the output of D-phenyllactic acid.
Embodiment
The invention provides a kind of regenerating coenzyme technique to high-efficiency and produce the method for D-phenyllactic acid, output is that single enzyme is produced more than 5 times of D-phenyllactic acid.The technical scheme that the present invention takes is that Pediococcus pentosaceus serum lactic dehydrogenase and Ogataea parapolymorpha hydrogenlyase are placed unified reaction system, constantly to wherein adding regenerating coenzyme substrate sodium formiate, making the continuous circulating reduction of oxidized form NAD is reduced coenzyme NADH, thereby realize the High-efficient Production of D-phenyllactic acid, be characterized in:
1, the enzyme of catalysis phenyl-pyruvic acid generation D-phenyllactic acid is D-lactic acid dehydrogenase in the reaction process, and its gene source is in Pediococcus pentosaceus ATCC 25745 (gene library is numbered GeneID:4417836); The enzyme that is used for the NADH regenerating coenzyme is hydrogenlyase, and its gene source is in Ogataea parapolymorpha DL-1 (gene library is numbered GI:320581066);
2, the D-lactic acid dehydrogenase that the present invention uses and hydrogenlyase can obtain by the genetic engineering bacterium overexpression, its preparation process can be sketched and be: with Pediococcus pentosaceus ATCC 25745, Ogataea parapolymorpha DL-1 genome is template, obtain D-lactic acid dehydrogenase and hydrogenlyase goal gene by PCR, utilize gene clone method to build up among the expression plasmid pET-22b (+), obtain to contain respectively D-lactic acid dehydrogenase, the recombinant plasmid of formate dehydrogenase gene, and recombinant plasmid transformed imported to make up recombinant bacterial strain in the intestinal bacteria, go out D-lactic acid dehydrogenase and hydrogenlyase through the IPTG abduction delivering, and with two kinds of enzymes process rough segmentations or refining, the enzyme reaction that is used for immediately the D-phenyllactic acid is synthetic;
3, in the enzyme reaction system, add phenyl-pyruvic acid as the substrate of synthetic D-phenyllactic acid, thereby sodium formiate is the regeneration that the cosubstrate of regenerating coenzyme promotes NADH in the reaction process, the concentration of enzymatic activity that adds D-lactic acid dehydrogenase is 0.1～100U/L, and the concentration of enzymatic activity of hydrogenlyase is 0.1～100U/L; The concentration of phenyl-pyruvic acid is 1～1000mmol/L, and the concentration of sodium formiate is 1～1000mmol/L, and the concentration of coenzyme NAD H is 0.01～100mmol/L simultaneously;
4, two enzyme couplings realize regenerating coenzyme, and the temperature of synthetic D-phenyllactic acid process is 20 ℃～70 ℃, and pH is 3.0～9.0, and the reaction times is 1～10h;
5, reaction process is in retort, D-lactic acid dehydrogenase, hydrogenlyase, substrate phenyl-pyruvic acid, sodium formiate, pH damping fluid are added in the retort according to above-mentioned addition, the backward coenzyme NAD H that wherein adds that stirs reacts to certain hour, and termination reaction gets final product.
6, detect the method for D-phenyllactic acid: reaction solution is through centrifugal, and again through filtering with microporous membrane (0.22 μ m), HPLC analyzes on the filtrate.HPLC condition: 1. Agilent1100 chromatographic column: ZORBAX 300SB C18 (5 μ m, 4.6 * 250mm); 2. moving phase: (A) 0.05% trifluoroacetic acid/methyl alcohol and (B) 0.05% trifluoroacetic acid/water; 3. gradient elution program: 0, the elutriant A/B volume ratio 18,20,21,24 minutes the time forms and was respectively 10: 90,100: 0,100: 0,10: 90,10: 90; 4. detector: UV-detector wavelength: 210nm; 5. column temperature: 30 ℃; 6. flow velocity: 1mL/min; 7. sample size: 10 μ L; 8. phenyllactic acid standard specimen concentration: 0.5mg/mL.
The present invention will be further described in detail below in conjunction with specific embodiment, but the invention is not restricted to following examples.
The acquisition of embodiment 1 Pediococcus pentosaceus D-lactic acid dehydrogenase and Ogataea parapolymorpha hydrogenlyase
The coding of gene in NCBI gene library of Pediococcus pentosaceus D-lactic acid dehydrogenase and Ogataea parapolymorpha hydrogenlyase is respectively GeneID:4417836 and GI:320581066, its gene order is known, can be by design PCR primer, take Pediococcus pentosaceus ATCC 25745, Ogataea parapolymorpha DL-1 genome as template, obtain D-lactic acid dehydrogenase and hydrogenlyase goal gene by PCR respectively.Respectively these two goal gene are built up among the expression plasmid pET-22b (+) by gene clone method, thereby obtain respectively to contain the recombinant plasmid of D-lactic acid dehydrogenase, formate dehydrogenase gene; Subsequently these two kinds of recombinant plasmid transformed are imported to and make up recombinant bacterial strain in the e. coli bl21 (DE3).
Above-mentioned BL21 (DE3) recombinant bacterium in the LB substratum 37 ℃ to be cultured to the 600nm absorbance value be 0.6 o'clock, add inductor IPTG to final concentration 0.5mmol/L, 30 ℃ of inducing culture 5h subsequently can obtain the thalline of goal gene overexpression.Subsequently, obtain thick enzyme or the pure enzyme of Pediococcus pentosaceus D-lactic acid dehydrogenase and Ogataea parapolymorpha hydrogenlyase by ultrasonic or the ordinary methods such as high pressure is broken, centrifugal, chromatography, for the biosynthetic Cofactor Regeneration Systems of D-phenyllactic acid.
The synthetic D-phenyllactic acid of regenerating coenzyme method under the embodiment 2 all temps conditions
In 1L enzyme reaction tank, add 10U/L Pediococcus pentosaceus D-lactic acid dehydrogenase, 10U/LOgataea parapolymorpha hydrogenlyase, 10mmol/L phenyl-pyruvic acid, 10mmol/L sodium formiate and 0.2mmol/L NADH, reaction buffer is 100mmol/L phosphoric acid buffer (pH 6.0), temperature of reaction system is respectively 20,30,40,45,50,55,60,65 and 70 ℃, detect synthetic D-phenyllactic acid output behind the reaction 1h, experimental result is referring to table 1.
The synthetic output of D-phenyllactic acid under the table 1 differential responses temperature condition
| Temperature (℃) | 20 | 30 | 40 | 45 | 50 | 55 | 60 | 65 | 70 |
| D-phenyllactic acid (mmol/L) | 4.3 | 5.6 | 6.6 | 7.8 | 7.2 | 5.6 | 4.9 | 3.2 | 2.6 |
The synthetic D-phenyllactic acid of regenerating coenzyme method under the embodiment 3 various pH conditions
In 1L enzyme reaction tank, add 10U/L Pediococcus pentosaceus D-lactic acid dehydrogenase, 10U/L Ogataea parapolymorpha hydrogenlyase, 10mmol/L phenyl-pyruvic acid, 10mmol/L sodium formiate and 0.2mmol/L NADH, temperature of reaction is controlled at 45 ℃, reaction system pH is respectively 3,4,5,6,7,8 and 9, detect synthetic D-phenyllactic acid output behind the reaction 1h, experimental result is referring to table 2.
The synthetic output of D-phenyllactic acid under the table 2 differential responses temperature condition
| pH | 3 | 4 | 5 | 6 | 7 | 8 | 9 |
| D-phenyllactic acid (mmol/L) | 5.9 | 6.5 | 7.2 | 7.8 | 6.5 | 4.4 | 2.1 |
The synthetic D-phenyllactic acid of regenerating coenzyme method under the embodiment 4 differential responses time conditions
In 1L enzyme reaction tank, add 10U/L Pediococcus pentosaceus D-lactic acid dehydrogenase, 10U/L Ogataea parapolymorpha hydrogenlyase, 10mmol/L phenyl-pyruvic acid, 10mmol/L sodium formiate and 0.2mmol/L NADH, reaction pH and temperature are respectively pH 6.0 and 45 ℃, detect respectively synthetic D-phenyllactic acid output behind reaction 0.25,0.5,0.75,1,1.25,1.5 and 2h, experimental result is referring to table 3.
The synthetic output of D-phenyllactic acid under the table 3 differential responses time conditions
| Time (h) | 0.25 | 0.5 | 0.75 | 1 | 1.25 | 1.5 | 2 |
| D-phenyllactic acid (mmol/L) | 2.9 | 5.6 | 7.2 | 7.8 | 7.9 | 7.8 | 7.5 |
Comparative Examples 1
This Comparative Examples provides a kind of enzymatic synthesis method of D-phenyllactic acid, and is specific as follows:
In 1L enzyme reaction tank, add 10U/L Pediococcus pentosaceus D-lactic acid dehydrogenase, 10mmol/L phenyl-pyruvic acid and 0.2mmol/L NADH, reaction pH and temperature are respectively pH 6.0 and 45 ℃, and detecting synthetic D-phenyllactic acid output behind the reaction 2h is 0.15mmol/L.
Above-described embodiment only is explanation technical conceive of the present invention and characteristics, and its purpose is to allow the personage who is familiar with technique can understand content of the present invention and according to this enforcement, can not limit protection scope of the present invention with this.All equivalences that spirit is done according to the present invention change or modify, and all should be encompassed within protection scope of the present invention.
Claims (10)
1. the enzymatic synthesis method of a D-phenyllactic acid, it makes phenyl-pyruvic acid that hydrogenation reduction generation D-phenyllactic acid occur under the D-lactic acid dehydrogenase catalysis and in the presence of the reduced coenzyme NADH, in the reaction system when reacting initial, the concentration of phenyl-pyruvic acid is 1 ~ 1000 mmol/L, the concentration of enzymatic activity of D-lactic acid dehydrogenase is 0.1 ~ 100 U/L, the concentration of reducibility coenzyme NADH is 0.01 ~ 100 mmol/L, it is characterized in that: also adding in the reaction system of described hydrogenation reduction has hydrogenlyase and sodium formiate, when reacting initial, the concentration of enzymatic activity of hydrogenlyase is 0.1 ~ 100 U/L, the concentration of sodium formiate is 1 ~ 1000 mmol/L, the temperature of described hydrogenation reduction is 20 ℃ ~ 70 ℃, the pH of reaction system is 3.0 ~ 9.0, and the reaction times is 0.5 ~ 10 h.
2. the enzymatic synthesis method of D-phenyllactic acid according to claim 1, it is characterized in that: the temperature of described hydrogenation reduction is 30 ℃ ~ 60 ℃.
3. the enzymatic synthesis method of D-phenyllactic acid according to claim 2, it is characterized in that: the temperature of described hydrogenation reduction is 40 ℃ ~ 50 ℃.
4. according to claim 1 and 2 or the enzymatic synthesis method of 3 described D-phenyllactic acids, it is characterized in that: the pH of described reaction system is 3 ~ 7.
5. the enzymatic synthesis method of D-phenyllactic acid according to claim 4, it is characterized in that: the pH of described reaction system is 5 ~ 6.
6. the enzymatic synthesis method of D-phenyllactic acid according to claim 5, it is characterized in that: the described reaction times is 0.5 ~ 2 hour.
7. the enzymatic synthesis method of D-phenyllactic acid according to claim 6, it is characterized in that: the described reaction times is 0.75 ~ 1.5 hour.
8. the enzymatic synthesis method of D-phenyllactic acid according to claim 1, it is characterized in that: in the reaction system when reacting initial, the concentration of phenyl-pyruvic acid is 1 ~ 100 mmol/L, the D-lactic acid dehydrogenase concentration of enzymatic activity is 1 ~ 100 U/L, the concentration of reducibility coenzyme NADH is 0.1 ~ 10mmol/L, the concentration of enzymatic activity of hydrogenlyase is 1 ~ 100 U/L, and the concentration of sodium formiate is 1 ~ 100mmol/L.
9. the enzymatic synthesis method of D-phenyllactic acid according to claim 8, it is characterized in that: the concentration of phenyl-pyruvic acid is 1 ~ 50 mmol/L, the concentration of enzymatic activity of D-lactic acid dehydrogenase is 1 ~ 50 U/L, the concentration of reducibility coenzyme NADH is 0.1 ~ 2mmol/L, the concentration of enzymatic activity of hydrogenlyase is 1 ~ 50 U/L, and the concentration of sodium formiate is 1 ~ 50mmol/L.
10. the enzymatic synthesis method of the described D-phenyllactic acid of each claim according to claim 1 ~ 3 and in 8 ~ 9, it is characterized in that: the gene source of described D-lactic acid dehydrogenase is in Pediococcus pentosaceus ATCC 25745, and the gene source of described hydrogenlyase is in Ogataea parapolymorpha DL-1.
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Cited By (8)
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| CN104845988A (en) * | 2015-05-19 | 2015-08-19 | 常熟理工学院 | Construction and expression of D-LDH-FDH fusion gene capable of improving D-phenyllactic acid yield |
| CN105543291A (en) * | 2016-02-15 | 2016-05-04 | 江南大学 | Microbial transformation method |
| CN105603008A (en) * | 2016-02-15 | 2016-05-25 | 江南大学 | Microorganism converting method |
| CN105603006A (en) * | 2016-02-15 | 2016-05-25 | 江南大学 | Microorganism converting method |
| CN105624217A (en) * | 2016-02-15 | 2016-06-01 | 江南大学 | Microbial transformation method |
| CN109136310A (en) * | 2018-10-10 | 2019-01-04 | 无锡富泽药业有限公司 | A kind of preparation method of New uracils |
| CN109837321A (en) * | 2017-11-29 | 2019-06-04 | 中国科学院大连化学物理研究所 | A kind of restoring method of NAD analog |
| KR20200078429A (en) * | 2020-04-20 | 2020-07-01 | 주식회사 휴온스내츄럴 | Novel Phenyllactic acid producing Pediococcus acidilactici HBT strain and its culture |
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| CN104130967B (en) * | 2014-08-11 | 2017-12-19 | 南京林业大学 | One plant of coexpression L lactic dehydrogenase and the Escherichia coli of hydrogenlyase and its construction method and application |
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| CN104845988B (en) * | 2015-05-19 | 2018-11-20 | 常熟理工学院 | A kind of construction and expression for the D-LDH-FDH fusion enhancing D- phenyl-lactic acid yield |
| CN104845988A (en) * | 2015-05-19 | 2015-08-19 | 常熟理工学院 | Construction and expression of D-LDH-FDH fusion gene capable of improving D-phenyllactic acid yield |
| CN105624217B (en) * | 2016-02-15 | 2019-03-15 | 江南大学 | A kind of method of microorganism conversion |
| CN105603006A (en) * | 2016-02-15 | 2016-05-25 | 江南大学 | Microorganism converting method |
| CN105624217A (en) * | 2016-02-15 | 2016-06-01 | 江南大学 | Microbial transformation method |
| CN105603008A (en) * | 2016-02-15 | 2016-05-25 | 江南大学 | Microorganism converting method |
| CN105603008B (en) * | 2016-02-15 | 2019-03-15 | 江南大学 | A kind of method of microorganism conversion |
| CN105603006B (en) * | 2016-02-15 | 2019-03-15 | 江南大学 | A kind of method of microorganism conversion |
| CN105543291A (en) * | 2016-02-15 | 2016-05-04 | 江南大学 | Microbial transformation method |
| CN105543291B (en) * | 2016-02-15 | 2019-07-23 | 江南大学 | A kind of method of microorganism conversion |
| CN109837321A (en) * | 2017-11-29 | 2019-06-04 | 中国科学院大连化学物理研究所 | A kind of restoring method of NAD analog |
| CN109837321B (en) * | 2017-11-29 | 2023-01-13 | 中国科学院大连化学物理研究所 | Reduction method of NAD analogue |
| CN109136310A (en) * | 2018-10-10 | 2019-01-04 | 无锡富泽药业有限公司 | A kind of preparation method of New uracils |
| KR20200078429A (en) * | 2020-04-20 | 2020-07-01 | 주식회사 휴온스내츄럴 | Novel Phenyllactic acid producing Pediococcus acidilactici HBT strain and its culture |
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