CN103224963B - Method for preparing chiral amine through asymmetric reduction under catalysis of marine strain - Google Patents
Method for preparing chiral amine through asymmetric reduction under catalysis of marine strain Download PDFInfo
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Abstract
The invention provides a method for preparing chiral amine through asymmetric reduction under the catalysis of a marine strain, and relates to chiral amine. The method comprises the following steps: inoculating a strain into a 216L culture medium, culturing, then centrifuging the obtained fermentation liquid to obtain cells, and redissolving and washing with a buffer solution, thus preparing cell sap; and adding ketone used as a substrate into the obtained cell sap, then adding an amino donor and a cosubstrate for cyclic regeneration of coenzyme, and performing asymmetric reduction and amination under the catalysis of the cells, thus obtaining the chiral amine product. The new strain which contains NADH (nicotinamide adenine dinucleotide)-dependent amine dehydrogenase and is different from strains reported before is obtained through the screening of marine microorganisms, and the reaction system and reaction conditions of preparing chiral amine through the asymmetric reduction and amination of ketone under the catalysis of full cells of the strain are optimized. The optical purity of the obtained chiral amine product is up to 90% or above, and the yield is up to 70% or above. The method provided by the invention is convenient to operate, has the advantages of high optical purity of the product, high yield and the like, is simple in equipment and has better industrial application prospects in the field of preparing chiral amine under biological catalysis.
Description
Technical field
The present invention relates to a kind of Chiral Amine, especially relate to a kind of method that marine bacteria strain catalytic asymmetric reduction prepares Chiral Amine.
Background technology
Chiral Amine is important medicine and fine-chemical intermediate, also can be used as the chiral source [Applied Organometallic Chemistry, 2011,25:110-116] of metal chiral ligand and chiral auxiliary(reagent), the asymmetric reduction of catalysis of carbonyl.Chiral Amine can also be used for racemate resolution as chiral selectors.Chiral Amine is by chemosynthesis and biocatalysis preparation.The chemical preparation process of Chiral Amine mainly contains: the reduction of amino acid or derivatives thereof, aldehydes or ketones and the coupling of imines and the amination open loop etc. of epoxy compounds.Biological preparation Chiral Amine realizes mainly through enzyme catalysis fractionation or asymmetric reduction.
Enzyme for the preparation of Chiral Amine mainly contains lipase, transaminase and oxydo-reductase.Lipase (Lipase) catalysis can split racemic amine acquisition Chiral Amine, and theoretical yield is 50%, and there is the problem [Journal of the AmericanChemical Society, 2010,132:14179-14190] of later separation.Utilizing transaminase (Transaminases) catalysis hydroxyl ketone generation transamination to react is the main method preparing chiral amino alcohol at present.Transaminase can transamination between catalytic amino donor (amino acid or amine) and amino acceptor (ketone).This reaction is reversible reaction, due to generate ketone and amine all have more serious restraining effect to transaminase, product ketone must be removed to reduce it to enzyme level, reaction forward is impelled to carry out, space-time yield lower [ChemicalCommunications, 2010,46:5569-5571].
The amination of catalysis ketone group asymmetric reduction obtains Chiral Amine, and is the amine dehydrogenase of coenzyme with NAD (P) H, is the desirable biological catalyst preparing chiral amino alcohol, and its reaction scheme is succinct, easily realizes regenerating coenzyme.Abrahamson etc. carry out taking turns rite-directed mutagenesis to the leucine dehydrogenase deriving from Bacillus stereothermophilus more, obtain novel amine desaturase, and alternative reduction methyl iso-butyl ketone (MIBK) is (R)-1,3-dimethylbutyl amine.This enzyme catalysis asymmetric amine is reduced, and transformation efficiency can reach 92%, and activity is 0.69U/mg, and product ee value is 99.8% [Angewandte Chemie International Edition.201251:3969-3972].The people such as Itoh separation and purification from Streptomyces virginiae IFO12827 obtains the amine dehydrogenase relying on coenzyme NAD H, under the condition of pH10, the amination of catalysis series hydroxyl ketone body powder generates amino alcohol, during pH7, catalytic amino alcohol generates corresponding hydroxyl ketone [Journal of Molecular Catalysis B-Enzymatic in the other direction, 2000,10:281-290.].But the reaction preference of this enzyme still belongs to lower, and without the report of the information such as gene and protein structure.Therefore, the bacterial strain of amine dehydrogenase of screening containing catalytic asymmetric reduction amination high-activity high-selectivity realizes the key that Chiral Amine effectively prepared.
Summary of the invention
A kind of marine bacteria strain catalytic asymmetric reduction is the object of the present invention is to provide to prepare the method for Chiral Amine.
The present invention includes following steps:
1) enchylema preparation: bacterial classification is accessed in 216L substratum and cultivate, the more centrifugal acquisition cell of fermented liquid will obtained after cultivation, washing resuspended with damping fluid, is mixed with enchylema;
2) whole-cell catalytic reaction: in the enchylema that step 1) obtains, add ketone as substrate, then add amino group donor and cosubstrate, for coenzyme cyclic regeneration, utilize the amination of cell catalysis asymmetric reduction to obtain product Chiral Amine.
In step 1), described bacterial classification is Kiel pseudomonas (Pseudomonas kilonensis), Kiel pseudomonas (Pseudomonas kilonensis) obtains from Chinese marine microorganism culture presevation administrative center, and the deposit number at this center is MCCC NO.1A06062; The described strain inoculation amount of cultivating in 216L substratum that accessed by bacterial classification can be 1%; Described 216L substratum consist of 10.0g/L peptone, 5.0g/L yeast powder, 0.5g/L extractum carnis, 0.5g/L Trisodium Citrate, 0.2g/LNH4NO3,1.0g/L NaAc, prepares with seawater; The condition of described cultivation can be: initial pH7.0, and liquid amount volume fraction is 10%, culture temperature 30 DEG C, shaking speed 150rpm, incubation time 72h; Describedly centrifugally adopt refrigerated centrifuge, centrifugal condition can be 4 DEG C, 10000rpm, 15min, obtains cell; Described damping fluid is resuspended, washing can abandon supernatant liquor, and damping fluid is resuspended, centrifugal after washing, repetitive operation 3 times; The concentration of described enchylema can be 0.025 ~ 100g/L; The pH that described damping fluid can be selected from 0.01 ~ 0.2mol/L is at least one in the Tris-hydrochloric acid, sodium acetate, sodium carbonate, potassiumphosphate etc. of 7 ~ 13, the Tris-hydrochloride buffer of preferred pH9.
In step 2) in, described ketone can be selected from the one in the aliphatic ketone, aromatic ketone, hydroxyketone etc. of the carbon chain lengths 2 ~ 10 of 0.001 ~ 0.5mol/L; Described amino group donor can be selected from L-Ala, ammoniacal liquor, the NH of 0.002 ~ 1mol/L
4cl, NH
4nO
3, one in amino alkane etc., preferred ammoniacal liquor or NH
4cl; Described cosubstrate can be selected from least one in the glucose, glycerine, ethanol, formic acid, Virahol, sec-butyl alcohol etc. of 0.001 ~ 1mol/L, at least one in preferred glucose, glycerine etc.; The described condition utilizing the amination of cell catalysis asymmetric reduction is pH7 ~ 13, temperature of reaction 0 ~ 70 DEG C, concussion speed 100 ~ 300rpm, reaction times 30 ~ 180h.
The new strains that the difference that the present invention obtains from marine microorganism screening the amine dehydrogenase containing dependence NADH was reported in the past.The present invention has also investigated the impacts such as amino group donor, reaction buffer, pH, temperature, optimizes reaction system and reaction conditions that Chiral Amine is prepared in this strain whole-cell catalysis ketone asymmetric reduction amination.The optical purity of obtained product Chiral Amine reaches more than 90%, and yield reaches more than 70%.The present invention is easy to operate, has that optical purity of products is high, yield advantages of higher, and equipment is simple, prepares Chiral Amine field have good prospects for commercial application in biocatalysis.
Accompanying drawing explanation
Fig. 1 is the stratographic analysis figure of ketone.
Fig. 2 is the chiral chromatographic analysis figure of product amine.
Embodiment
Below by embodiment, the present invention is elaborated.
Embodiment 1
(1) cultivation of Kiel pseudomonas (Pseudomonas kilonensis): with the inoculum size of 1%, bacterial classification is accessed in 50L216L substratum.216L substratum consists of 10.0g/L peptone, 5.0g/L yeast powder, 0.5g/L extractum carnis, 0.5g/L Trisodium Citrate, 0.2g/L NH
4nO
3, 1.0g/L NaAc, prepares with seawater.Culture condition is: initial pH7.0, and liquid amount volume fraction is 10%, culture temperature 30 DEG C, shaking speed 150rpm, incubation time 72h.
The preparation of cell: cultivate the fermented liquid terminating to obtain, centrifugal in refrigerated centrifuge (4 DEG C, 10000rpm, 15min) obtain cell, abandon supernatant liquor, precipitation Tris-HCl damping fluid (pH7.6) is resuspended, centrifugal after abundant washing, repetitive operation obtains cell 3 times.
(2) whole-cell catalytic reaction: reaction system is 0.5mol/L4-methyl 2 pentanone, 1mol/L L-Ala, 1mol/L glycerine, the Tris-hydrochloride buffer of 0.01mol/L, pH9.0, reaction volume 100L, the cell of 100g/L, reaction volume 50mL, under 0 DEG C of temperature of reaction, 100rpm shakes reaction response time 180h.
(3) be separated and detect: regulating pH to 14 with the NaOH of 6mol/L, extract with the methyl tertiary butyl ether of 50L again, isolated methyl tert-butyl ether layers anhydrous sodium sulphate dewaters, low-temperature vacuum drying, the mixed solution (volume ratio is 9: 1) of residual solid normal hexane and Virahol is dissolved, detect with high performance liquid chromatography, product R-4-methyl 2-amylamine optical purity is e.e99.0%, productive rate 84.7%.Product mass spectra analytical data is 1H NMR (400MHz, CDCl3) δ 2.94 (sex, 1H, J=6.4Hz), 1.65 (sep, 1H, 6.8Hz), 1.24-1.02 (m, 2H), 1.04 (d, 3H, 6.4Hz), 0.89 (d, 6H, 6.8Hz).
Embodiment 2
(1) experimental procedure is as (1) ~ (2) of embodiment 1.
(2) whole-cell catalytic reaction: reaction system is 0.02mol/L2-butanone, 0.2mol/L NH
4cl, 0.2mol/L glucose, the sodium acetate buffer of 0.01mol/L, the cell of 1.5g/L, reaction system pH13, reaction volume 500mL, at 50 DEG C, 200rpm shakes reaction, reaction times 30h.
(3) be separated and detect: regulating pH to 14 with the NaOH of 6mol/L, extract with the methyl tertiary butyl ether of 250mL again, isolated methyl tert-butyl ether layers anhydrous sodium sulphate dewaters, low-temperature vacuum drying, the mixed solution (volume ratio is 9: 1) of residual solid normal hexane and Virahol is dissolved, detect with high performance liquid chromatography, the yield of calculating product amine R-2-butylamine is 72.1%, e.e. value is 92.7%.
Embodiment 3
(1) experimental procedure is as (1) ~ (2) of embodiment 1.
(2) whole-cell catalytic reaction: reaction system is 0.01mol/L methyl phenyl ketone, 0.02mol/L ammoniacal liquor, 0.01mol/L Virahol, the Tris-hydrochloride buffer of 0.2mol/L, the cell of 0.025g/L, reaction volume 20L, reaction system pH7, reaction volume 5L, at 10 DEG C, 300rpm shakes reaction, reaction times 180h.
(3) be separated and detect: regulating pH to 14 with the NaOH of 6mol/L, extract with the methyl tertiary butyl ether of 10L again, isolated methyl tert-butyl ether layers anhydrous sodium sulphate dewaters, low-temperature vacuum drying, the mixed solution (volume ratio is 9: 1) of residual solid normal hexane and Virahol is dissolved, detect with high performance liquid chromatography, product S-phenylethylamine yield is 80.7%, e.e. value is 90.2%.
Embodiment 4
(1) experimental procedure is as (1) ~ (2) of embodiment 1.
(2) whole-cell catalytic reaction: reaction system is 0.01mol/L5-decanone, 0.01mol/L2-aminopropane, 0.02mol/L sec-butyl alcohol, the potassium phosphate buffer of 0.2mol/L, the cell of pH10,50g/L, reaction volume 50L, under 50 DEG C of temperature of reaction, 300rpm shakes reaction, reaction times 30h.
(3) be separated and detect: regulating pH to 14 with the NaOH of 6mol/L, extract with the methyl tertiary butyl ether of 25L again, isolated methyl tert-butyl ether layers anhydrous sodium sulphate dewaters, low-temperature vacuum drying, the mixed solution (volume ratio is 9: 1) of residual solid normal hexane and Virahol is dissolved, detect with high performance liquid chromatography, product S-5-decyl amine yield is 88.6%, e.e. value is 95.5%.
Embodiment 5
(1) experimental procedure is as (1) ~ (2) of embodiment 1.
(2) whole-cell catalytic reaction: reaction system is 0.05mol/L2-hydroxyl-3-butanone, 0.1mol/L L-Ala, 0.05mol/L ethanol, the sodium carbonate buffer of 0.2mol/L, the cell of pH9.0,250mg/L, reaction volume 1L, under 70 DEG C of temperature of reaction, 300rpm shakes reaction, reaction times 30h.
(3) be separated and detect: regulating pH to 14 with the NaOH of 6mol/L, extract with the methyl tertiary butyl ether of 0.5L again, isolated methyl tert-butyl ether layers anhydrous sodium sulphate dewaters, low-temperature vacuum drying, the mixed solution (volume ratio is 9: 1) of residual solid normal hexane and Virahol is dissolved, detect with high performance liquid chromatography, R-2-hydroxyl-3-butylamine yield is 80.1%, e.e. value is 98.5%.
Embodiment 6
(1) experimental procedure is as (1) ~ (2) of embodiment 1.
(2) whole-cell catalytic reaction: reaction system is 0.04mol/L3-hydroxyl-5-heptanone, 0.2mol/L NH
4nO
3, 0.001 ~ 0.2mol/L formic acid, the Tris-hydrochloride buffer of 0.01mol/L, the cell of 1000mg/L, reaction volume 1.5L, reaction system pH11, under 70 DEG C of temperature of reaction, 100-300rpm shakes reaction, reaction times 30 ~ 180h.
(3) be separated and detect: regulating pH to 14 with the NaOH of 6mol/L, extract with the methyl tertiary butyl ether of 40mL again, isolated methyl tert-butyl ether layers anhydrous sodium sulphate dewaters, low-temperature vacuum drying, the mixed solution (volume ratio is 9: 1) of residual solid normal hexane and Virahol is dissolved, detect with high performance liquid chromatography, product S-3-hydroxyl-5-heptyl amice yield is 89.9%, e.e. value is 98.4%.
Embodiment 7
(1) experimental procedure is as (1) ~ (2) of embodiment 1.
(2) whole-cell catalytic reaction: reaction system is 0.2mol/L3-hexanone, 0.2mol/L NH
4cl, 0.2mol/L glycerine, the sodium acetate buffer of 0.4mol/L, the cell of 50g/L, reaction system pH12, reaction volume 80L, at 70 DEG C, 200rpm shakes reaction, reaction times 95h.PH to 14 is regulated with the NaOH of 6mol/L, extract with the methyl tertiary butyl ether of 400mL again, isolated methyl tert-butyl ether layers anhydrous sodium sulphate dewaters, low-temperature vacuum drying, the mixed solution (volume ratio is 9: 1) of residual solid normal hexane and Virahol is dissolved, detect with high performance liquid chromatography, the yield of calculating product R-3-hexylamine is 71.5%, e.e. value is 92.7%
Embodiment 8
(1) experimental procedure is as (1) ~ (2) of embodiment 1.
(2) whole-cell catalytic reaction: catalytic reaction system is the different octanone of 0.001mol/L2-, 0.002mol/L ammoniacal liquor, 0.002mol/L ethanol, the sodium acetate buffer of 0.01-0.2mol/L, the cell of 1.5g/L, reaction system pH8, reaction volume 2L, at 50 DEG C, 200rpm shakes reaction, reaction times 30h.
(3) be separated and detect: regulating pH to 14 with the NaOH of 6mol/L, extract with the methyl tertiary butyl ether of 400mL again, isolated methyl tert-butyl ether layers anhydrous sodium sulphate dewaters, low-temperature vacuum drying, the mixed solution (volume ratio is 9: 1) of residual solid normal hexane and Virahol is dissolved, detect with high performance liquid chromatography, the yield of calculating product S-2-octodrine amine is 91.5%, e.e. value is 95.7%.
The separation of the product Chiral Amine obtained by the present invention is as follows with detection:
Use NaOH adjust ph, then extract with methyl tertiary butyl ether, isolated methyl tert-butyl ether layers anhydrous sodium sulphate dewaters, low-temperature vacuum drying.Dissolved by the mixed solution of residual solid normal hexane and Virahol, the concentration high performance liquid chromatography of ketone detects, the concentration of product amine and Enantiomer excess value high-performance liquid chromatogram determination.
Described separation condition is regulate pH to 14 with the NaOH of 6mol/L, then extracts with methyl tertiary butyl ether, and isolated methyl tert-butyl ether layers anhydrous sodium sulphate dewaters, low-temperature vacuum drying.Described testing conditions is that the concentration high performance liquid chromatography of ketone detects, and chromatographic column is C18 post, determined wavelength 210nm; The concentration of described product amine and Enantiomer excess value (e.e. value), high performance liquid chromatography detects, and chromatographic column is Chiracel-OD column (Daicel), determined wavelength 214nm.
The concentration high performance liquid phase of ketone detects, and chromatographic column is C18 post, determined wavelength 210nm(Fig. 1).Product amine high performance liquid chromatography detects ee value, and chromatographic column is Chiracel-OD column (Daicel), determined wavelength 214nm(Fig. 2).
Strain whole-cell catalysis ketone asymmetric reduction amination preparation of the present invention, it is the high enantiomeric selectivity utilizing amine dehydrogenase in full cell, the asymmetric reduction amination of catalysis ketone, obtain R-amine or S-amine, the cosubstrates such as glucose add the cyclic regeneration for coenzyme NAD H.It is that the chemical equation of cosubstrate is as follows with glucose:
The molecular structural formula of the ketone involved by reaction system is as general formula (I):
The molecular structural formula of amine involved in reaction system is as general formula (II):
Wherein R
1, R
2the alkyl of C2-10, aromatic base or hydroxyl.They all optionally can be substituted with a substituent one or many.
Claims (13)
1. marine bacteria strain catalytic asymmetric reduction prepares a method for Chiral Amine, it is characterized in that comprising the following steps:
1) enchylema preparation: bacterial classification is accessed in 216L substratum and cultivate, the more centrifugal acquisition cell of fermented liquid will obtained after cultivation, washing resuspended with damping fluid, is mixed with enchylema; Described bacterial classification is Kiel pseudomonas (Pseudomonas kilonensis), Kiel pseudomonas (Pseudomonas kilonensis) has been preserved in Chinese Sea Microbiological Culture Collection administrative center, and deposit number is MCCC NO.1A06062; The described strain inoculation amount of cultivating in 216L substratum that accessed by bacterial classification is 1%; Described 216L substratum consist of 10.0g/L peptone, 5.0g/L yeast powder, 0.5g/L extractum carnis, 0.5g/L Trisodium Citrate, 0.2g/LNH
4nO
3, 1.0g/LNaAc, prepares with seawater;
2) whole-cell catalytic reaction: in step 1) in the enchylema that obtains, add ketone as substrate, then add amino group donor and cosubstrate, for coenzyme cyclic regeneration, utilize the amination of cell catalysis asymmetric reduction to obtain product Chiral Amine.
2. a kind of marine bacteria strain catalytic asymmetric reduction prepares the method for Chiral Amine as claimed in claim 1, it is characterized in that in step 1) in, the condition of described cultivation is: initial pH 7.0, liquid amount volume fraction is 10%, culture temperature 30 DEG C, shaking speed 150rpm, incubation time 72h.
3. a kind of marine bacteria strain catalytic asymmetric reduction prepares the method for Chiral Amine as claimed in claim 1, it is characterized in that in step 1) in, described centrifugal employing refrigerated centrifuge, centrifugal condition is 4 DEG C, 10000rpm, 15min, obtains cell.
4. a kind of marine bacteria strain catalytic asymmetric reduction prepares the method for Chiral Amine as claimed in claim 1, it is characterized in that in step 1) in, described damping fluid method that is resuspended, washing abandons supernatant liquor, and damping fluid is resuspended, centrifugal after washing, repetitive operation 3 times.
5. a kind of marine bacteria strain catalytic asymmetric reduction prepares the method for Chiral Amine as claimed in claim 1, it is characterized in that in step 1) in, the concentration of described enchylema is 0.025 ~ 100g/L.
6. a kind of marine bacteria strain catalytic asymmetric reduction prepares the method for Chiral Amine as claimed in claim 1, it is characterized in that in step 1) in, the pH that described damping fluid is selected from 0.01 ~ 0.2mol/L is Tris-hydrochloric acid, sodium acetate, sodium carbonate, at least one in potassiumphosphate of 7 ~ 13.
7. a kind of marine bacteria strain catalytic asymmetric reduction prepares the method for Chiral Amine as claimed in claim 6, it is characterized in that described damping fluid is the Tris-hydrochloride buffer of pH 9.
8. a kind of marine bacteria strain catalytic asymmetric reduction prepares the method for Chiral Amine as claimed in claim 1, it is characterized in that in step 2) in, described ketone is selected from the one in the aliphatic ketone of the carbon chain lengths 2 ~ 10 of 0.001 ~ 0.5mol/L, aromatic ketone, hydroxyketone.
9. a kind of marine bacteria strain catalytic asymmetric reduction prepares the method for Chiral Amine as claimed in claim 1, it is characterized in that in step 2) in, described amino group donor is selected from L-Ala, ammoniacal liquor, the NH of 0.002 ~ 1mol/L
4cl, NH
4nO
3, one in amino alkane.
10. a kind of marine bacteria strain catalytic asymmetric reduction prepares the method for Chiral Amine as claimed in claim 9, it is characterized in that described amino group donor is ammoniacal liquor or NH
4cl.
11. as claimed in claim 1 a kind of marine bacteria strain catalytic asymmetric reduction prepare the method for Chiral Amine, it is characterized in that in step 2) in, described cosubstrate is selected from least one in the glucose of 0.001 ~ 1mol/L, glycerine, ethanol, formic acid, Virahol, sec-butyl alcohol.
12. as claimed in claim 11 a kind of marine bacteria strain catalytic asymmetric reduction prepare the method for Chiral Amine, it is characterized in that described cosubstrate is selected from least one in glucose, glycerine.
13. as claimed in claim 1 a kind of marine bacteria strain catalytic asymmetric reduction prepare the method for Chiral Amine, it is characterized in that in step 2) in, the described condition of cell catalysis asymmetric reduction amination that utilizes is pH 7 ~ 13, temperature of reaction 0 ~ 70 DEG C, concussion speed 100 ~ 300rpm, reaction times 30 ~ 180h.
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| CN105567756A (en) * | 2016-02-01 | 2016-05-11 | 厦门大学 | Marine bacterial strain and method for preparing chiral amine from catalyzing of amine dehydrogenase of marine bacterial strain |
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| CN104152384B (en) * | 2014-08-08 | 2016-08-24 | 厦门大学 | A kind of method that marine bacteria strain catalytic asymmetric reduction prepares chirality phenylalanine |
| CN105112468B (en) * | 2015-10-14 | 2019-01-08 | 厦门大学 | A kind of method of multienzyme couple system preparation Chiral Amine |
| CN105712812B (en) * | 2016-01-25 | 2019-03-01 | 西北农林科技大学 | Utilize the chiral beta-Amines and its method of the preparation of asymmetric reduction aminating reaction |
| US11118200B2 (en) | 2017-07-06 | 2021-09-14 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Method for preparing amines from aldehydes and ketones by biocatalysis |
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| CN105567756A (en) * | 2016-02-01 | 2016-05-11 | 厦门大学 | Marine bacterial strain and method for preparing chiral amine from catalyzing of amine dehydrogenase of marine bacterial strain |
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