CN110279974A - A kind of chemical-biological mixed method using flavo-enzyme degradation 2,4,6- trinitrotoluene - Google Patents
A kind of chemical-biological mixed method using flavo-enzyme degradation 2,4,6- trinitrotoluene Download PDFInfo
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- CN110279974A CN110279974A CN201910651016.1A CN201910651016A CN110279974A CN 110279974 A CN110279974 A CN 110279974A CN 201910651016 A CN201910651016 A CN 201910651016A CN 110279974 A CN110279974 A CN 110279974A
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- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
- A62D3/02—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by biological methods, i.e. processes using enzymes or microorganisms
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B09—DISPOSAL OF SOLID WASTE; RECLAMATION OF CONTAMINATED SOIL
- B09C—RECLAMATION OF CONTAMINATED SOIL
- B09C1/00—Reclamation of contaminated soil
- B09C1/10—Reclamation of contaminated soil microbiologically, biologically or by using enzymes
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F3/00—Biological treatment of water, waste water, or sewage
- C02F3/34—Biological treatment of water, waste water, or sewage characterised by the microorganisms used
- C02F3/342—Biological treatment of water, waste water, or sewage characterised by the microorganisms used characterised by the enzymes used
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- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/40—Inorganic substances
- A62D2101/45—Inorganic substances containing nitrogen or phosphorus
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
- C02F2101/38—Organic compounds containing nitrogen
Abstract
The invention discloses a kind of chemical-biological mixed methods using flavo-enzyme degradation 2,4,6-trinitrotoluene, comprising the following steps: (1) is chemically modified to obtain product OH-TNT or H-TNT to achieve the purpose that enhance TNT nitro negative electrical charge by TNT；(2) obtained product is subjected to enzymatic degradation and the product after degradation is handled.This method has product single, and no nitro reduzate makes phenyl ring remove aromatization, is expected to realize the advantages such as TNT open loop degradation.
Description
Technical field
The present invention relates to nitryl aromatic class degradation technical fields, and in particular to and it is a kind of to utilize flavo-enzyme degradation 2,4,
The chemical-biological mixed method of 6- trinitrotoluene.
Background technique
Nitryl aromatic class compound is compound that is a kind of while having aromatic rings and nitro functions, is widely used in
The military affairs such as dyestuff, insecticide, explosive, pesticide and civil field.In the production and use process of chemical products, a large amount of nitro
Aromatic substance is released in environment water and soil, by biological concentration and the transmitting of food chain, to microorganism, plant,
The ecological environment of animal and surrounding causes to seriously threaten.
TNT has that impact sensitivity is low, detonation performance is good, cheap as most popular nitro aromatic compound explosive
The advantages that.But TNT is also a kind of toxic pollutant simultaneously, when the TNT concentration in air is 0.85mgcm-3When, it can lead
Mean corpuscular volume in blood is caused to increase, mean corpusular hemoglobin and mean corpuscular hemoglobin concentration (MCHC) are significant
It reduces.It is found by long-term epidemiological surveillance, Long Term Contact TNT can cause to can lead to whole blood when the white interior severe of Poisoning thin
Born of the same parents are reduced, and cause the poisonous effects such as cataract, toxic hepatitis, jaundice, alpastic anemia, neurotrosis.
However since the molecule of TNT is sufficiently stable symmetrical, it is difficult to pass through the biodegrade side of common aromatic compounds
Method is degraded, i.e., carries out open loop degradation to phenyl ring by phenyl ring hydroxylated oxygenase or phenyl ring cuttingization oxygenase.Report at present
Main two kinds of the TNT enzymatic degradation approach in road, one is nitro also original route, i.e., by restoring the nitro on TNT phenyl ring
It is amido come the TNT that degrades, secondly being Mai Senhaimo also original route, i.e., by being hydrogenated to Mai Senhaimoization on TNT aromatic rings
Close degradation of the object realization to TNT.However, nitro also original route the problems such as that there are intermediate products is toxic, degradation is not thorough；Mai Senhai
It is silent to go back original route then and be considered as a kind of path for being expected to realize TNT open loop degradation by the means such as protonating and hydrolyzing.At present
Experiment only finds the pure enzyme of three kinds of TNT that can degrade by Mai Senhaimo approach, is respectively as follows: X pentaerythrite tetranitro reductase
(PENTR), xenobiotic reductase (XENBR), n-ethylmaleimide reductase (NEMR).Regrettably, experiment hair
Now when using TNT as substrate, these three enzymes can also be with the nitre of a variety of high poisons while through Mai Senhaimo approach degradation TNT
Base reduzate generates.The generation of the nitro reduzate of a large amount of high poisons is unfavorable for the protein expression bacterium that enzymatic degradation is relied on
The growth of strain (such as enterobacter cloacae, Pseudomonas fluorescens), or even there is toxic action.
Summary of the invention
In order to overcome the above technical defects, flavo-enzyme degradation 2,4,6-trinitrotoluene is utilized the present invention provides a kind of
(TNT) chemical-biological mixed method.This method has product single, and no nitro reduzate makes phenyl ring remove aromatization, has
It hopes and realizes the advantages such as TNT open loop degradation.
In order to reach above-mentioned technical effect, the present invention provides the following technical scheme that
A kind of chemical-biological mixed method using flavo-enzyme degradation 2,4,6-trinitrotoluene, comprising the following steps:
(1) TNT is chemically modified to obtain product OH-TNT or H-TNT to achieve the purpose that enhance TNT nitro negative electrical charge；(2) will
Obtained product carries out enzymatic degradation and handles the product after degradation.
Further technical solution is that the preparation method of H-TNT is specially by TNT or to contain TNT's in the step (1)
Mixture and sodium borohydride are dissolved in deionized water, and hand concussion is sufficiently mixed system, then carries out heating water bath, makes body
It is that temperature maintains 50 DEG C reaction is hydrolyzed, obtains the product H-TNT of chemical modification, it is molten that acidic buffer is added after the completion of hydrolysis
Liquid makes system PH be maintained at 7, and temperature is maintained at 37 DEG C.
Further technical solution is that the preparation method of OH-TNT is specially by TNT or to contain TNT in the step (1)
Mixture be dissolved in phosphate buffer solution, keep solution PH 11.7, hand concussion is sufficiently mixed system, then carries out
Heating water bath makes system temperature maintain 50 degree and reaction is hydrolyzed, the product OH-TNT of chemical modification obtained, after the completion of hydrolysis
Acidic buffer solution is added, so that system PH is maintained at 7, temperature is maintained at 37 DEG C.
Further technical solution is that the preparation method of the phosphate buffer solution is by potassium dihydrogen phosphate and phosphoric acid hydrogen two
Potassium carries out quantitative mixing, and NaOH, which is then added, makes buffer solution 11.7 PH at room temperature, and suitable deionized water dissolving is added,
Finally obtain phosphate buffer solution.
Further technical solution is that the mass ratio of the potassium dihydrogen phosphate and dipotassium hydrogen phosphate is 1:13.
Further technical solution is that the ratio of the TNT and deionized water is 50mM:20ml.
Further technical solution is that the TNT and phosphate buffer solution ratio are 50mM:20ml.
Further technical solution is that the step (2) is specially to be added to pass through in the reaction system that step (1) obtains
Genetic engineering modifies the coli strain that can produce flavo-enzyme, and the nutrients of Anabacty and IPTZ as microorganism is added
Matter carries out enzymatic biodegrade.
Further technical solution is that the ratio of the Anabacty and IPTZ are 200g:0.4mM.
Further technical solution is that the flavo-enzyme is selected from xenobiotic reductase, pentaerythritol tetranitrate also
Any one in protoenzyme, morphine reductase, N- maleimide reductase and old yellow enzyme.
The present invention utilizes molecular dynamics software AMBER, and to H-TNT molecule, in five kinds of flavo-enzymes, (xenobiotic is restored
Enzyme (XENB), pentaerythritol tetranitrate reductase (PETNR), morphine reductase (MR), N- maleimide reductase
(NEMR) and old yellow enzyme (OYE)) activated centre simulated, it is found that the essential reason of the degradative pathway difference of H-TNT and TNT is
As caused by the electronic structure distributional difference of H-TNT and TNT.It is specifically compared to TNT, the upper nitro negative electricity of H-TNT
The stronger flavine enzyme active center residue that is easier to of lotus forms the strong interactions such as hydrogen bond, the coenzyme flavin adenine with activated centre
Mononucleotide (FMN) forms pi-pi accumulation structure, reduces the energy barrier of its Mai Senhaimo also original route, eventually by the way Mai Senhaimo
Diameter degradation.
Therefore, it is proposed that the strategy of chemical-biological mixed method degradation TNT a kind of, is to pass through chemical method first
Chemical modification appropriate is carried out to TNT, OH-TNT (anion) is such as generated by way of basic hydrolysis；By with sodium borohydride
Reaction generates H-TNT, to achieve the purpose that enhance negative electrical charge on its nitro, then using obtained chemical modifications as enzyme
The substrate of catalytic degradation carries out biodegrade by Mai Senhaimo approach.This method has product single, no nitro reduzate
(high poison), makes phenyl ring remove aromatization, is expected to realize the advantages such as TNT open loop degradation.
Detailed description of the invention
Fig. 1 is the comparison of TNT and H-TNT electrostatic potential and Partial charge；
Fig. 2 is conformation and its two paths reaction energy barriers of the TNT molecule in the activated centre OYE；
Fig. 3 is conformation and its two paths reaction energy barriers of the H-TNT molecule in the activated centre OYE；
Fig. 4 is the distribution of OH-TNT (anion) molecular electrostatic potential and the conformation in the activated centre PETNR.
Specific embodiment
Embodiment 1
A kind of chemical-biological mixed method using old yellow enzyme (OYE) degradation 2,4,6-trinitrotoluene, including following step
It is rapid:
(1) substrate stoichiometric is modified: by the TNT of 50mM or mixture containing TNT and sodium borohydride be dissolved in 20ml go from
In sub- water, hand concussion is sufficiently mixed system.Then heating water bath is carried out, so that system temperature is maintained 50 degree and is reacted,
Obtain the product (H-TNT) of chemical modification；
(2) appropriate acidic buffer solution being added after the completion of hydrolysis, system PH is made to be maintained at 7, temperature is maintained near 37 degree,
Enzymic catalytic reaction suitable for next step.
(3) modification substrate carries out enzymatic degradation: being added in the reaction system of step (2) can by genetic engineering modification
The coli strain of OYE is generated, and the IPTZ of Anabacty (carbenicillin) and 0.4mM of 200g is added
The nutriment of (isopropyl- β-D-thiogalactopyranoside) as microorganism carries out enzymatic biodegrade.
(4) catabolite post-processes: the mixture after biodegrade being taken out from reaction kettle and is dried.
Experiments have shown that: when using TNT as substrate, OYE cannot be worked as by Mai Senhaimo approach degradation TNT with chemical modification
Mono- hydrogen compound of Mai Senhaimo (H-TNT) of TNT afterwards can then be degraded when being substrate by Mai Senhaimo approach.OYE activity
Center residue is main, including Tyr196, His191, Asn194, Phe250, Asn294, Phe296 and Tyr375.Pass through Molecule Motion
Mechanical simulation finds TNT molecule in the conformation in activated centre as shown in Fig. 2, TNT and FMN do not form pi-pi accumulation structure.Pass through
Transactional analysis is we have found that the Phe250 and Phe296 in the activated centre OYE can form pi-pi accumulation with TNT molecule simultaneously.
It is calculated by reaction energy barrier, discovery nitro also original route energy barrier is lower than Mai Senhaimo also original route energy barrier, cannot pass through Mai Senhai
Silent approach is degraded.After substrate is changed to the stronger H-TNT of the negative electrical charge on nitro, discovery H-TNT can form π-with FMN
Pi accumulation structure, and nitro also original route energy barrier is higher than Mai Senhaimo also original route energy barrier, may finally pass through Mai Senhaimo approach
It degrades, H-TNT is as shown in Figure 3 in the activated centre OYE conformation and two paths reaction energy barriers.
Embodiment 2
A kind of chemical-biological mixed method using too peace enzyme (PETNR) degradation 2,4,6-trinitrotoluene, including it is following
Step:
(1) it configures buffer solution: potassium dihydrogen phosphate and dipotassium hydrogen phosphate being subjected to quantitative mixing, NaOH, which is then added, to be made to delay
Rushing solution, PH is that suitable deionized water dissolving is added, is finally settled to 20mL near 11.7 at room temperature.
(2) substrate stoichiometric is modified: the TNT of 50mM or the mixture containing TNT are dissolved in 20ml phosphate buffer solution,
Keep solution PH near 11.7, hand concussion is sufficiently mixed system.Then heating water bath is carried out, system temperature is maintained
50 degree are hydrolyzed reaction, obtain the product (OH-TNT (anion)) of chemical modification.
(3) equivalent acidic buffer solution is added after the completion of hydrolysis, system PH is made to be maintained at 7, temperature is maintained near 37 degree,
Enzymic catalytic reaction suitable for next step.
(4) modification substrate carries out enzymatic degradation: being added in the reaction system of step (3) can by genetic engineering modification
The coli strain of PETNR is generated, and the IPTZ of Anabacty (carbenicillin) and 0.4mM of 200g is added
The nutriment of (isopropyl- β-D-thiogalactopyranoside) as microorganism carries out enzymatic biodegrade.
(5) catabolite post-processes: the mixture after biodegrade being taken out from reaction kettle and is dried.
We are obtained H-TNT (radical), H-TNT (anion), OH- by carrying out different chemical modifications to TNT
The different types of TNT chemical modification object such as TNT (radical), and to its modified outcome electrostatic potential map, discovery: wherein OH-
TNT (anion) and H-TNT electrostatic potential branch are very much like.Existed by molecular dynamics simulation discovery OH-TNT (anion)
The activated centre PETNR can form pi-pi accumulation structure with FMN, and can also be by Nostoxanthin enzyme (PETNR) by the path Mai Senhaimo
It degrades, the distribution of OH-TNT (anion) molecular electrostatic potential and conformation in the activated centre PETNR are as shown in Figure 4.
Although reference be made herein to invention has been described for explanatory embodiment of the invention, and above-described embodiment is only this hair
Bright preferable embodiment, embodiment of the present invention are not limited by the above embodiments, it should be appreciated that those skilled in the art
Member can be designed that a lot of other modification and implementations, these modifications and implementations will fall in principle disclosed in the present application
Within scope and spirit.
Claims (10)
1. it is a kind of using flavo-enzyme degradation 2,4,6-trinitrotoluene chemical-biological mixed method, which is characterized in that including with
Lower step: (1) TNT is chemically modified to obtain mesh of the product OH-TNT or H-TNT to reach enhancing TNT nitro negative electrical charge
's；(2) obtained product is subjected to enzymatic degradation and the product after degradation is handled.
2. the chemical-biological mixed method according to claim 1 using flavo-enzyme degradation 2,4,6-trinitrotoluene,
It is characterized in that, the preparation method of H-TNT is specially that TNT or mixture containing TNT and sodium borohydride is molten in the step (1)
For solution in deionized water, hand concussion is sufficiently mixed system, then carries out heating water bath, make system temperature maintain 50 DEG C into
Row hydrolysis obtains the product H-TNT of chemical modification, acidic buffer solution is added after the completion of hydrolysis, is maintained at system PH
7, temperature is maintained at 37 DEG C.
3. the chemical-biological mixed method according to claim 1 using flavo-enzyme degradation 2,4,6-trinitrotoluene,
It is characterized in that, the preparation method of OH-TNT is specially that TNT or mixture containing TNT are dissolved in phosphoric acid in the step (1)
In buffer solution, keep solution PH 11.7, hand concussion is sufficiently mixed system, then carries out heating water bath, makes system temperature
Degree maintains 50 degree and reaction is hydrolyzed, and obtains the product OH-TNT of chemical modification, acidic buffer solution is added after the completion of hydrolysis,
System PH is set to be maintained at 7, temperature is maintained at 37 DEG C.
4. the chemical-biological mixed method according to claim 3 using flavo-enzyme degradation 2,4,6-trinitrotoluene,
It is characterized in that, the preparation method of the phosphate buffer solution is that potassium dihydrogen phosphate and dipotassium hydrogen phosphate are carried out to quantitative mixing, so
After NaOH is added, make buffer solution 11.7 PH at room temperature, suitable deionized water dissolving be added, finally obtains phosphoric acid buffer
Solution.
5. the chemical-biological mixed method according to claim 4 using flavo-enzyme degradation 2,4,6-trinitrotoluene,
It is characterized in that, the mass ratio of the potassium dihydrogen phosphate and dipotassium hydrogen phosphate is 1:13.
6. the chemical-biological mixed method according to claim 2 using flavo-enzyme degradation 2,4,6-trinitrotoluene,
It is characterized in that, the ratio of the TNT and deionized water is 50mM:20ml.
7. the chemical-biological mixed method according to claim 3 using flavo-enzyme degradation 2,4,6-trinitrotoluene,
It is characterized in that, the TNT and phosphate buffer solution ratio are 50mM:20ml.
8. the chemical-biological mixed method according to claim 1 using flavo-enzyme degradation 2,4,6-trinitrotoluene,
It is characterized in that, the step (2) is specially to be added to can produce by genetic engineering modification in the reaction system that step (1) obtains
The coli strain of flavo-enzyme, and the nutriment of Anabacty and IPTZ as microorganism is added, carry out enzymatic biology
Degradation.
9. the chemical-biological mixed method according to claim 8 using flavo-enzyme degradation 2,4,6-trinitrotoluene,
It is characterized in that, the ratio of the Anabacty and IPTZ are 200g:0.4mM.
10. the chemical-biological mixed method according to claim 8 using flavo-enzyme degradation 2,4,6-trinitrotoluene,
It is characterized in that, the flavo-enzyme be selected from xenobiotic reductase, pentaerythritol tetranitrate reductase, morphine reductase,
Any one in N- maleimide reductase and old yellow enzyme.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109234246A (en) * | 2018-10-10 | 2019-01-18 | 中国工程物理研究院化工材料研究所 | Regulation flavo-enzyme obtains the method and mutant for the mutant that TNT open loop can be made to degrade |
| CN110261212A (en) * | 2019-07-18 | 2019-09-20 | 中国工程物理研究院化工材料研究所 | A kind of composite pouring molding die of composite explosives tension test part |
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| CN109234246A (en) * | 2018-10-10 | 2019-01-18 | 中国工程物理研究院化工材料研究所 | Regulation flavo-enzyme obtains the method and mutant for the mutant that TNT open loop can be made to degrade |
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Cited By (2)
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| CN109234246A (en) * | 2018-10-10 | 2019-01-18 | 中国工程物理研究院化工材料研究所 | Regulation flavo-enzyme obtains the method and mutant for the mutant that TNT open loop can be made to degrade |
| CN110261212A (en) * | 2019-07-18 | 2019-09-20 | 中国工程物理研究院化工材料研究所 | A kind of composite pouring molding die of composite explosives tension test part |
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