CN100554403C - Oxidation microbacterium and utilize this oxidation microbacterium to prepare the method for optical pure chiral aryl secondary alcohol - Google Patents
Oxidation microbacterium and utilize this oxidation microbacterium to prepare the method for optical pure chiral aryl secondary alcohol Download PDFInfo
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- CN100554403C CN100554403C CNB2006101479663A CN200610147966A CN100554403C CN 100554403 C CN100554403 C CN 100554403C CN B2006101479663 A CNB2006101479663 A CN B2006101479663A CN 200610147966 A CN200610147966 A CN 200610147966A CN 100554403 C CN100554403 C CN 100554403C
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Abstract
The invention discloses a kind of oxidation microbacterium (Microbacterium oxydans) ECU2010, CGMCC NO.1875, and utilize the method for this oxidation microbacterium as the Preparation of Catalyst optical pure chiral aryl secondary alcohol.Described method places buffered soln to wherein adding the raceme aryl secondary alcohol in oxidation microbacterium cell, produces corresponding ketone and (S)-secondary alcohol through the catalytic enantioselective oxidation, reaction solution through separate, purifying obtains target product optical purity (S)-aryl secondary alcohol.Catalyzer of the present invention is easy to preparation, reaction conditions gentleness, and the productive rate of (S)-1-phenylethyl alcohol is up to 90% in an embodiment, and enantiomeric excess value has suitable industrial application DEVELOPMENT PROSPECT greater than 99%.
Description
Technical field
The present invention relates to a kind of microbacterium and uses thereof, more particularly relate to a kind of oxidation microbacterium and utilize this oxidation microbacterium to prepare the method for optical pure chiral aryl secondary alcohol.
Background technology
The optical activity chirality aryl secondary alcohol is chiral drug, agrochemicals, pheromone, condiment, spices, liquid crystal and chirality auxiliary material synthetic important intermediate, adopts at present usually the preparation method to comprise two big class methods: i.e. the kinetic resolution of the asymmetric reduction of prochiral ketone and raceme alcohol.For example, utilizing the enantioselective hydrolysis of the enantioselectivity esterification of esterase or lipase-catalyzed racemize secondary alcohol or transesterification fractionation and racemate to split is one of preparation optical activity chirality aryl secondary alcohol method, the major advantage of this method is: the kind of commodity lipase is more, can select the enzyme with high vigor and high enantioselectivity with comparalive ease at specific substrate.But the highest yield of this method target enantiomorph product is no more than 50%, hydrolysis for lipase-catalyzed racemate splits in addition, must synthesize racemic substrate ester in advance, for suitability for industrialized production, not only increase operation steps, and increased extra cost.The asymmetric reduction of prochiral ketone is the another kind of important method of preparation optical activity chirality alcohol, substrate ketone 100% ground can be converted into the chiral alcohol of single enantiomer on this theoretical method, has higher industrial application value.Chemical method uses chiral amino alcohol or transition metal complex etc. to realize the reduction of ketone as catalyzer to the asymmetric reduction of prochiral ketone usually.Though the catalytic ketone asymmetric reduction of chemical method has higher productive rate, but the stereoselectivity of reaction is often not ideal enough, the optical purity of product usually can not reach the requirement of pharmaceutical industry, and the preparation of chiral catalyst and reclaim relatively difficulty, price comparison costliness.The catalytic prochiral ketone asymmetric reduction of biological process has the high advantage of stereospecificity, and the optical purity of reduzate secondary alcohol is very high usually, is a current research focus.The employed biological catalyst of biological process catalysis ketone asymmetric reduction generally comprises desaturase preparation and the whole cell of microorganism active, present topmost shortcoming is to need regeneration reducing type coenzyme NAD H or NADPH in the reaction system, these coenzyme are very expensive, therefore are difficult to use in mass product production.The solution regenerating coenzyme problem of high efficiency, low cost is the key of this class methods industrialization success.Utilize the biocatalysis method optionally an enantiomorph of racemize aryl secondary alcohol to be oxidized to aryl ketones, can obtain optically active another kind of enantiomorph aryl secondary alcohol equally.This coenzyme that wherein relates to is mainly NAD
+Or NADP
+, its price will be far below coenzyme NAD H or NADPH.Therefore utilize this method to be expected to obtain the aryl secondary alcohol of high-optical-purity with lower regenerating coenzyme cost.The aryl ketones that biological dehydrogenation reaction generates can be used as the substrate of enantioselectivity complementary biological reducing reaction, and by bio-oxidation and connecting that biological reducing reacts, theoretical yield that promptly can 100% obtains optically pure aryl alcohol.For example, Tetrahedron:Asymmetry 2006, and 17:1769-1774, Yang Wei etc. once reported rhodotorula Rhodotorula sp.AS2.2241, can be (S)-1-phenylethyl alcohol with the methyl phenyl ketone asymmetric reduction.Oxidation microbacterium and the catalytic reaction combination of rhodotorula can be realized that the racemization of going of racemization 1-phenylethyl alcohol turns to (S)-1-phenylethyl alcohol.
Summary of the invention
Technical problem to be solved by this invention provides a kind of oxidation microbacterium of new screening, this bacterial strain separates from soil and obtains through behind the multi-turns screen, in on November 29th, 2006 in the preservation of Chinese common micro-organisms DSMZ, preserving number is CGMCC1875, and utilize the katalysis selective oxidation reaction of this oxidation microbacterium to prepare optical pure chiral aryl secondary alcohol, prepare the chiral aryl secondary alcohol of high-optical-purity (＞99%) with lower cost.
The technical solution used in the present invention: oxidation microbacterium (Microbacterium oxydans) ECU2010, CGMCC NO.1875.
Adopt the method for above-mentioned oxidation microbacterium, comprise the following steps: as the Preparation of Catalyst optical pure chiral aryl secondary alcohol
A. cultivate oxidation microbacterium (Microbacterium oxydans) ECU2010, CGMCCNO.1875 gets above-mentioned oxidation microbacterium cell then and places buffered soln;
B. add the raceme aryl secondary alcohol in above-mentioned buffered soln, produce corresponding ketone and (S)-secondary alcohol through the catalytic enantioselective oxidation, the general structure of wherein said raceme aryl secondary alcohol is: R
1CH (OH) R
2, substituent R
1Be selected from-C
6H
5Or-C
6H
4X, substituent R
2For-CH
3, substituent X is selected from-CH
3,-F ,-Cl ,-Br ,-I ,-OH ,-NH
2Or-NO
2One of them;
C. reaction solution obtains target product optical purity (S)-aryl secondary alcohol through separation, purifying.
Prepare the method for optical pure chiral aryl secondary alcohol, it is characterized in that: the microbacterium of oxidation described in reaction system cell concn is 5～100g (weight in wet base)/L.
Prepare the method for optical pure chiral aryl secondary alcohol, it is characterized in that: the concentration of described raceme aryl secondary alcohol described in the reaction system is 10～200mM.
Prepare the method for optical pure chiral aryl secondary alcohol, it is characterized in that: the temperature of reaction of step b is controlled to be 20～50 ℃, and the reaction times is 3～96 hours.
Prepare the method for optical pure chiral aryl secondary alcohol, it is characterized in that: described buffered soln is that the pH value is 6～8 buffer solution of potassium phosphate or Tris-HCl buffered soln.
The method for preparing optical pure chiral aryl secondary alcohol, it is characterized in that: can add the organic cosolvent that quality is a reaction system quality 0.2%～10% in the reaction system, described organic cosolvent is selected from one or more the mixture in methyl alcohol, ethanol, dimethyl sulfoxide (DMSO), the dimethyl formamide.
Prepare the method for optical pure chiral aryl secondary alcohol, it is characterized in that: the aryl secondary alcohol of raceme described in the step b is the 1-phenylethyl alcohol.
Prepare the method for optical pure chiral aryl secondary alcohol, it is characterized in that: after step b reaction finishes, can in reaction system, add rhodotorula (Rhodotorula sp.) ECU316-1CGMCC NO.1735.
Beneficial effect of the present invention, the present invention adopts new oxidation microbacterium as catalyzer the raceme aryl secondary alcohol to be carried out the chiral aryl secondary alcohol that the enantioselectivity oxidizing reaction is prepared high-optical-purity (＞99%), catalyzer is easy to preparation, reaction conditions gentleness, has certain industrial application DEVELOPMENT PROSPECT.The productive rate of (S)-1-phenylethyl alcohol can reach 90% in an embodiment, and enantiomeric excess value is greater than 99%.
Embodiment
Below by embodiment the present invention is described in further detail: oxidation microbacterium cell of the present invention (Microbacterium oxydans) ECU2010 is a kind of bacterial strain that belongs to the bacterium Bacteroides, this bacterial strain is to separate from soil, and obtain behind the process multi-turns screen, in on November 29th, 2006 in the preservation of Chinese common micro-organisms DSMZ, preserving number is CGMCC1875.Bacterial classification of the present invention has following microbial characteristic:
1. morphological specificity:
This bacterial strain is yellow bacterium colony, and smooth surface is translucent, and neat in edge is seen glossy to light.
2. physiological and biochemical property:
(1) Gram-positive rod bacterium; Aerobic bacteria;
(2) catalase experiment: the positive;
(3) oxydase experiment: feminine gender;
(4) starch hydrolysis experiment: feminine gender;
(5) gelatin liquification test: feminine gender;
(6) nitrate reduction test: feminine gender
(7) glycitols fermentation test
Positive: seminose, sucrose, maltose, glycerine, starch and inositol
Negative: D-glucose, D-N.F,USP MANNITOL, lactose, pectinose, sorbyl alcohol, rhamnosyl
(8) lysine decarboxylase test: feminine gender;
(9) urease test: feminine gender;
(10) growth optimal temperature: 25～35 ℃;
According to above physiological and biochemical test and " common bacteria system identification handbook ", " the outstanding Bacteria Identification handbook of uncle, this bacterium is oxidation microbacterium (Microbacterium oxydans), according to the 16SrDNA molecular biology identification, the homology of this bacterium and oxidation microbacterium (Microbacterium oxydans) is 99%.
Adopt the method for above-mentioned oxidation microbacterium as the Preparation of Catalyst optical pure chiral aryl secondary alcohol, comprise the following steps: that a. cultivates oxidation microbacterium (Microbacterium oxydans) ECU2010, CGMCC NO.1875 gets above-mentioned oxidation microbacterium cell then and places buffered soln; B. add the raceme aryl secondary alcohol in above-mentioned buffered soln, produce corresponding ketone and (S)-secondary alcohol through the catalytic enantioselective oxidation, the general structure of wherein said raceme aryl secondary alcohol is: R
1CH (OH) R
2, substituent R
1Be selected from-C
6H
5Or-C
6H
4X, substituent R
2For-CH
3, substituent X is selected from-CH
3,-F ,-Cl ,-Br ,-I ,-OH ,-NH
2Or-NO
2One of them; C. reaction solution obtains target product optical purity (S)-aryl secondary alcohol through separation, purifying.The microbacterium of oxidation described in reaction system cell concn is 5～100g (weight in wet base)/L.The concentration of described raceme aryl secondary alcohol described in the reaction system is 10～200mM.The temperature of reaction of step b is controlled to be 20～50 ℃, and the reaction times is 3～96 hours.Described buffered soln is that the pH value is 6～8 buffer solution of potassium phosphate or Tris-HCl buffered soln.Can add the organic cosolvent that quality is a reaction system quality 0.2%～10% in the reaction system, described organic cosolvent is selected from one or more the mixture in methyl alcohol, ethanol, dimethyl sulfoxide (DMSO), the dimethyl formamide, preferred dimethyl sulfoxide (DMSO).The preferred 1-phenylethyl alcohol of the aryl secondary alcohol of raceme described in the step b.
After finishing, step b reaction can in reaction system, add rhodotorula (Rhodotorula sp.) ECU316-1 CGMCC NO.1735, and the mass ratio (weight in wet base/weight in wet base) of red yeast cell and oxidation microbacterium cell is preferably 2: 1～and 100: 1.Red yeast cell can catalysis the first step reaction generation ketone be (S)-secondary alcohol with its selective reduction, through above-mentioned two step selectivity complementary redox reactions, can improve and go racemization to be converted into the productive rate of (S)-secondary alcohol raceme secondary alcohol.
Embodiment 1
Culture medium prescription is: glucose 15.0g/L, yeast extract paste 5.0g/L, peptone 5.0g/L, KH
2PO
41.0g/L, K
2HPO
43H
2O 0.5g/L, NaCl 1.0g/L, MgSO
40.5g/L pH 7.0.Get the oxidation microbacterium slant strains of 4 ℃ of preservations, picking one ring is seeded to the 250ml that the 50ml substratum is housed and shakes in the bottle, and under 30 ℃, 48h, centrifugal cell harvesting are cultivated in the 160rpm jolting.The fermentation broth enzyme vigor is about 20～40U/L, and the about 10～20g of cell concn (weight in wet base)/L, the enzyme activity of unit cell are the 2U/g wet cell.Cell viability unit is defined as: at 30 ℃, under the condition of pH 7.0, the oxidation of per minute catalysis 1-phenylethyl alcohol generates the required cell concentration of 1.0 μ mol methyl phenyl ketones.
Embodiment 2
Get the above-mentioned oxidation microbacterium cell of weight in wet base 1.0g, be suspended in (0.1M in the 9.5ml sodium phosphate salt buffered soln, pH 7.5), add 24mg 1-phenylethyl alcohol and 0.5ml dimethyl sulfoxide (DMSO), reaction mixture jolting reaction on 30 ℃, the constant temperature shaking table of 160r/min, intermittent sampling is with ethyl acetate extraction, analyze the enantiomeric excess value and the productive rate of residue substrate with chirality gas-chromatography (chromatographic column is β-DEX120 kapillary chirality gas chromatographic column), react after 24 hours, the productive rate of residue (S)-1-phenylethyl alcohol is 47%, and enantiomeric excess value (e.e.) is 98%.
Embodiment 3
Get the above-mentioned oxidation microbacterium cell of weight in wet base 1.0g, be suspended in (0.1M in the 9.5ml sodium phosphate salt buffered soln, pH 7.5), add 31mg 1-(4-aminomethyl phenyl) ethanol and 0.5ml dimethyl sulfoxide (DMSO), reaction mixture is at 30 ℃, jolting reaction on the constant temperature shaking table of 160r/min, intermittent sampling is with ethyl acetate extraction, analyze the enantiomeric excess value and the productive rate of residue substrate with chirality gas-chromatography (chromatographic column is β-DEX120 kapillary chirality gas chromatographic column), react after 72 hours, residue (S)-1-(4-aminomethyl phenyl) ethanol yield is 46%, and enantiomeric excess value (e.e.) is 97%.
Embodiment 4
Get the above-mentioned oxidation microbacterium cell of weight in wet base 1.0g, be suspended in (0.1M in the 9.5ml sodium phosphate salt buffered soln, pH 7.5), add 31mg 1-(2-chloro-phenyl-) ethanol and 0.5ml dimethyl sulfoxide (DMSO), reaction mixture is at 30 ℃, jolting reaction on the constant temperature shaking table of 160r/min, intermittent sampling is with ethyl acetate extraction, analyze the enantiomeric excess value and the productive rate of residue substrate with chirality gas-chromatography (chromatographic column is β-DEX120 kapillary chirality gas chromatographic column), react after 60 hours, residue (S)-1-(2-chloro-phenyl-) ethanol yield is 48%, and enantiomeric excess value (e.e.) is 96%.
Embodiment 5
Get the above-mentioned oxidation microbacterium cell of weight in wet base 1.0g, be suspended in (0.1M in the 9.5ml sodium phosphate salt buffered soln, pH 7.5), add 28mg 1-(2-fluorophenyl) ethanol and 0.5ml dimethyl sulfoxide (DMSO), reaction mixture is at 30 ℃, jolting reaction on the constant temperature shaking table of 160r/min, intermittent sampling is with ethyl acetate extraction, analyze the enantiomeric excess value and the productive rate of residue substrate with chirality gas-chromatography (chromatographic column is β-DEX120 kapillary chirality gas chromatographic column), react after 48 hours, residue (S)-1-(2-fluorophenyl) ethanol yield is 45%, and enantiomeric excess value (e.e.) is 98%.
Embodiment 6
Press embodiment 1 described culture medium prescription, the preserving number of getting 4 ℃ of preservations is that CGMCC1875 oxidation microbacterium slant strains and preserving number are rhodotorula (Rhodotorula sp.ECU316-1) slant strains of CGMCC1735, picking one ring is seeded to the 500ml that the 100ml substratum is housed respectively and shakes in the bottle, at 30 ℃, 160r/min jolting cultivation 48h, centrifugal cell harvesting places 4 ℃ of refrigerators to preserve.Get the oxidation microbacterium cell of weight in wet base 1.0g, be suspended in (0.1M in the 9.5ml sodium phosphate salt buffered soln, pH 7.5), add 24mg 1-phenylethyl alcohol and 0.5ml dimethyl sulfoxide (DMSO), reaction mixture jolting reaction after 12 hours on 30 ℃, the constant temperature shaking table of 160r/min, the red yeast cell that adds the 4.0g weight in wet base continues reaction 18 hours, and the productive rate that obtains (S)-1-phenylethyl alcohol is 90%, and enantiomeric excess value is greater than 99%.
Above said content only is the basic explanation of the present invention under conceiving, and according to any equivalent transformation that technical scheme of the present invention is done, all should belong to protection scope of the present invention.
Claims (9)
1. oxidation microbacterium (Microbacterium oxydans) ECU2010, CGMCC NO.1875.
2. with the method for the described oxidation microbacterium of claim 1, comprise the following steps: as the Preparation of Catalyst optical pure chiral aryl secondary alcohol
A. cultivate oxidation microbacterium (Microbacterium oxydans) ECU2010, CGMCCNO.1875 gets above-mentioned oxidation microbacterium cell then and places buffered soln;
B. add the raceme aryl secondary alcohol in above-mentioned buffered soln, produce corresponding ketone and (S)-secondary alcohol through the catalytic enantioselective oxidation, the general structure of wherein said raceme aryl secondary alcohol is: R
1CH (OH) R
2, substituent R
1Be selected from-C
6H
5Or-C
6H
4X, substituent R
2For-CH
3, substituent X is selected from-CH
3,-F ,-Cl ,-Br ,-I ,-OH ,-NH
2Or-NO
2One of them;
C. reaction solution obtains target product optical purity (S)-aryl secondary alcohol through separation, purifying.
3. according to the described method for preparing optical pure chiral aryl secondary alcohol of claim 2, it is characterized in that: the microbacterium of oxidation described in reaction system cell concn is every liter of 5～100g/, in weight in wet base.
4. according to the described method for preparing optical pure chiral aryl secondary alcohol of claim 2, it is characterized in that: the concentration of the aryl secondary alcohol of raceme described in the reaction system is 10～200mM.
5. according to the described method for preparing optical pure chiral aryl secondary alcohol of claim 2, it is characterized in that: the temperature of reaction of step b is controlled to be 20～50 ℃, and the reaction times is 3～96 hours.
6. according to the described method for preparing optical pure chiral aryl secondary alcohol of claim 2, it is characterized in that: described buffered soln is that the pH value is 6～8 buffer solution of potassium phosphate or Tris-HCl buffered soln.
7. according to the described method for preparing optical pure chiral aryl secondary alcohol of claim 2, it is characterized in that: can add the organic cosolvent that quality is a reaction system quality 0.2%～10% in the reaction system, described organic cosolvent is selected from one or more the mixture in methyl alcohol, ethanol, dimethyl sulfoxide (DMSO), the dimethyl formamide.
8. according to the described method for preparing optical pure chiral aryl secondary alcohol of claim 2, it is characterized in that: the aryl secondary alcohol of raceme described in the step b is the 1-phenylethyl alcohol.
9. according to any one described method for preparing optical pure chiral aryl secondary alcohol of claim 2～8, it is characterized in that: finish the back in step b reaction and in reaction system, add rhodotorula (Rhodotorulasp.) ECU316-1 CGMCC NO.1735.
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