CN103289922A - Yokenella sp. and application thereof in preparing alpha, beta-unsaturated enol and aromatic alcohol - Google Patents
Yokenella sp. and application thereof in preparing alpha, beta-unsaturated enol and aromatic alcohol Download PDFInfo
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Abstract
The invention provides a novel bacterial strain-Yokenella sp. WZY002 and an application thereof in preparing alpha, beta-unsaturated olefine aldehyde (ketone) through regioselective reduction and aromatic alcohol through aromatic aldehyde (ketone) reduction. The bacterial strain is preserved in the China general microbiological culture collection center (CCTCC); the address is 430072, Wuhan University, Wuhan, China; the preservation number is CCTCC No: M2013099; the preservation date is March 22, 2013. The novel bacterial strain has the main beneficial effects of high regioselectivity, high stereoselectivity and high enzymatic activity, regioselective reduction of the alpha, beta-unsaturated enol is catalyzed so as to obtain various alpha, beta-unsaturated olefine aldehydes, and reduction of the aromatic aldehyde (ketone) can also be catalyze so as to obtain the aromatic alcohol. The bacterial strain is served as a biocatalyst and has high regioselectivity, high stereoselectivity and strong catalytic activity, the catalytic reaction does not need to add coenzyme, the reaction temperature is moderate, and the novel bacterial strain has a relatively high application value for industrial production.
Description
(1) technical field
The present invention relates to the new bacterial strain of a strain---Yokenella (Yokenella sp.) WZY002, and at regioselectivity reduction α, β-unsaturated olefine aldehydr or α, β-unsaturated ketenes prepares α, application in β-unsaturated enol, the asymmetric reduction aromatic ketone prepares the chirality aromatic alcohol, and the reduction aromatic aldehyde prepares the application in the aromatic alcohol.
(2) background technology
α, β-unsaturated enol is very important organic synthesis (it is synthetic to contain medicine) intermediate, be widely used in spices, medicine and other fine chemicals production as styryl carbinol, lemon alcohol, crotyl alcohol etc., be often used as food using additive, fragrance blender and medicine intermediate etc., have higher economic worth.
α, the selective hydrogenation of β-unsaturated olefine aldehydr (ketone) is the committed step of synthetic perfume, medicine intermediate etc.Because in that C=C key on the thermodynamics is lower than the activation energy of C=O key, the C=C key is more active than C=O key on kinetics, and under the effect of generalization chemical catalyst, α, the primary product of β-unsaturated olefine aldehydr (ketone) mostly is saturated aldehyde (ketone), more valuable product α, the yield of β-unsaturated enol is lower.Different with chemical catalyst is, biological catalyst has more excellent regioselectivity, can be only to α, and the C=O key selective hydrogenation of β-unsaturated olefine aldehydr (ketone) and obtain corresponding α, β-unsaturated enol.The reaction conditions gentleness of biological catalyst, stereoselectivity height, environmental friendliness, be easy to the deficiency that advantages such as Separation and Recovery and production cost be low have also remedied chemical catalyst.At present, biological catalysis prepares α, and β-unsaturated enol mainly is by selective reduction α, and β-unsaturated olefine aldehydr (ketone) is realized.Utilize the Yokenella microorganism catalysis to prepare α but have not yet to see, the report of β-unsaturated enol.
(3) summary of the invention
The invention provides the bacterial strain that a strain has high regioselectivity, highly-solid selectively and high vigor---Yokenella WZY002 and at α, the application in the pure and mild aromatic alcohol biological process preparation of β-ethylenic unsaturation.The reducible α of this bacterial strain, β-unsaturated olefine aldehydr (ketone) obtains α, and β-unsaturated enol also can obtain the chirality aromatic alcohol by the asymmetric reduction aromatic ketone, and also reducible aromatic aldehyde obtains aromatic alcohol.The reaction specificity is strong, and selectivity is good, the vigor height, and reaction need not add coenzyme.
The technical solution used in the present invention is:
Yokenella (Yokenella sp.) WZY002 is preserved in Chinese typical culture collection center, the address: China, Wuhan, Wuhan University, 430072, deposit number: CCTCC No:M2013099, preservation date: on March 22nd, 2013.
The 16S rDNA sequence of Yokenella WZY002 of the present invention is as follows:
ACATGCAAGTCGAACGGTAGCACAGAGGAGCTTGCTCCTTGGGTGACGAGTGG CGGACGGGTGAGTAATGTCTGGGAAACTGCCCGATGGAGGGGGATAACTACTG GAAACGGTAGCTAATACCGCATAATGTCGCAAGACCAAAGAGGGGGACCTTCG GGCCTCTTGCCATCGGATGTGCCCAGATGGGATTAGCTAGTAGGTGGGGTAACG GCTCACCTAGGCGACGATCCCTAGCTGGTCTGAGAGGATGACCAGCCACACTGG AACTGAGACACGGTCCAGACTCCTACGGGAGGCAGCAGTGGGGAATATTGCAC AATGGGCGCAAGCCTGATGCAGCCATGCCGCGTGTATGAAGAAGGCCTTCGGGT TGTAAAGTACTTTCAGCGGGGAGGAAGGCGATACGGTTAATAACCGTGTCGATT GACGTTACCCGCAGAAGAAGCACCGGCTAACTCCGTGCCAGCAGCCGCGGTAA TACGGAGGGTGCAAGCGTTAATCGGAATTACTGGGCGTAAAGCGCACGCAGGC GGTCTGTCAAGTCGGATGTGAAATCCCCGGGCTCAACCTGGGAACTGCATCCGA AACTGGCAGGCTAGAGTCTTGTAGAGGGGGGTAGAATTCCAGGTGTAGCGGTG AAATGCGTAGAGATCTGGAGGAATACCGGTGGCGAAGGCGGCCCCCTGGACAA AGACTGACGCTCAGGTGCGAAAGCGTGGGGAGCAAACAGGATTAGATACCCTG GTAGTCCACGCCGTAAACGATGTCGACTTGGAGGTTGTGCCCTTGAGGCGTGGC TTCCGGAGCTAACGCGTTAAGTCGACCGCCTGGGGAGTACGGCCGCAAGGTTA AAACTCAAATGAATTGACGGGGGCCCGCACAAGCGGTGGAGCATGTGGTTTAAT TCGATGCAACGCGAAGAACCTTACCTACTCTTGACATCCACGGAATTTAGCAGA GATGCTTTAGTGCCTTCGGGAACCGTGAGACAGGTGCTGCATGGCTGTCGTCAG CTCGTGTTGTGAAATGTTGGGTTAAGTCCCGCAACGAGCGCAACCCTTATCCTTT GTTGCCAGCGGTTCGGCCGGGAACTCAAAGGAGACTGCCAGTGATAAACTGGA GGAAGGTGGGGATGACGTCAAGTCATCATGGCCCTTACGAGTAGGGCTACACAC GTGCTACAATGGCATATACAAAGAGAAGCGACCTCGCGAGAGCAAGCGGACCT CATAAAGTATGTCGTAGTCCGGATCGGAGTCTGCAACTCGACTCCGTGAAGTCG GAATCGCTAGTAATCGTGGATCAGAATGCCACGGTGAATACGTTCCCGGGCCTT GTACACACCGCCCGTCACACCATGGGAGTGGGTTGCAAAAGAAGTAGGTAGCTT AACCTTCGGGAGGGCGCTTACCACTTTGTGATTCATGA
Bacterial strain screening process of the present invention is as follows:
Sample collecting: screen used soil sample respectively from Shandong, ground collection such as Hubei, the Inner Mongol.Yokenella WZY002 screening is from the vegetable soil of Jianli County, Jingzhou City, Chinese Hubei Province.
Dull and stereotyped primary dcreening operation: take by weighing the sterilized water that the 0.5g soil sample adds 1mL, shake up, leave standstill, supernatant liquor is got its 100 μ L applying solid flat board then with 1000 times of sterilized water dilutions, places 3～5 minutes, draw 100 μ L2-butenols (crotyl alcohol) and be coated with above-mentioned flat board again, be inverted incubated overnight for 30 ℃.Single bacterium colony that picking grows is transferred in the solid test tube slant, 30 ℃ of incubated overnight.The component of solid medium: peptone 1%, yeast extract 0.5%, NaCl0.5%, agar 2%, pH7.0～7.2,121 ℃ sterilization 20min.Substratum of the present invention is formed all with quality volume percent (W/V) expression, as containing this component of 1g in certain concentration of component 1% expression 100mL substratum.
To fermention medium, its component is as follows with the inclined-plane inoculation: peptone 1%, yeast extract 0.5%, NaCl0.5%, pH7.0～7.2,121 ℃ sterilization 20min.30 ℃ of shaking speed 200rpm cultivated 24～48 hours, obtained thalline after centrifugal to be suspended in the buffer solution system.
The wet thallus that obtains according to the method described above, be suspended in the buffer solution system, add α, beta-unsaturated aldehyde (ketone) or aromatic aldehyde (ketone) react, react after 1～72 hour, analyze substrate and its converted product with chirality gas-chromatography or gaseous mass spectrum coupling.
The invention still further relates to described Yokenella WZY002 at the α of regioselectivity reduction, β-unsaturated olefine aldehydr (ketone) preparation α, the application in β-unsaturated enol.
Preferably, described α, β-unsaturated olefine aldehydr (ketone) are one of following: crotonic aldehyde, 2-hexenoic aldehyde, 2-methyl-2-pentenals, 2-octenal, 2-decenal, citral, phenylacrolein, mesityl oxide, jononeionone, 3-octene-2-ketone and 4-methoxyl group-3-butene-2-ketone.
The invention still further relates to described Yokenella WZY002 and prepare application in the chirality aromatic alcohol at the asymmetric reduction aromatic ketone.
Preferably, described aromatic ketone is one of following: methyl phenyl ketone, 2-bromoacetophenone, 4-bromoacetophenone, 2-hydroxy acetophenone, benzylideneacetone.
The invention still further relates to described Yokenella WZY002 and prepare application in the aromatic alcohol at the reduction aromatic aldehyde.
Preferably, described aromatic aldehyde is phenyl aldehyde or Vanillin.
Described α, the regioselectivity reduction of β-unsaturated olefine aldehydr (ketone) and the reduction of aromatic aldehyde (ketone) have catalysis activity in pH6～9.5, preferably carry out in pH6.0～8.0 Sodium phosphate dibasics-phosphate sodium dihydrogen buffer solution or pH8.0～9.0Tris-HCl damping fluid.
Described α, the regioselectivity reduction of β-unsaturated olefine aldehydr (ketone) and the reduction of aromatic aldehyde (ketone) are carried out in the presence of glucose, ethanol, glycerine or Virahol.
Concrete, described reaction is: with α, β-unsaturated olefine aldehydr (ketone) or aromatic aldehyde (ketone) are substrate, be catalyzer with Yokenella WZY002 wet thallus, in the damping fluid of pH6～9, concentration of substrate 5～200mM, under 4～60 ℃ and shaking speed 0～200rpm, reacted 2～72 hours, reaction finishes by ethyl acetate extraction, the centrifugal organic phase that obtains, behind anhydrous sodium sulfate drying, the substrate in the organic phase and converted product thereof are carried out gaseous mass spectrum coupling and chirality gas chromatographic analysis.Wet thallus is 45～450g/L with respect to the addition of described damping fluid.
Concrete, described Yokenella WZY002 wet thallus can make as follows: fermention medium is formed: peptone 10g/L, yeast extract 5g/L, NaCl5g/L, solvent is water, pH7.0～7.2 are inoculated in Yokenella WZY002 in the fermention medium, cultivate 12～48 hours under 30 ℃, the condition of shaking speed 200rpm, the gained fermented liquid is at the centrifugal 10min of 10000rpm, abandon supernatant liquor, thalline washs once with the damping fluid of pH6～9, and the gained wet thallus is biological catalyst.
Beneficial effect of the present invention is mainly reflected in: provide a strain to have the bacterial strain of high regioselectivity, highly-solid selectively and high vigor---Yokenella WZY002, by this bacterial strain catalysis α, the also proper energy of β-unsaturated olefine aldehydr (ketone) and aromatic aldehyde (ketone) obtains α, β-unsaturated enol and aromatic alcohol.This bacterial strain is as biological catalyst, regioselectivity and stereoselectivity height, and catalytic activity is strong, and the reaction of institute's catalysis does not need to add coenzyme, and the reaction conditions gentleness has higher using value in suitability for industrialized production.
(4) description of drawings
Fig. 1 is Yokenella WZY002 phylogenetic tree.
(5) embodiment
The present invention is described further below in conjunction with specific embodiment, but protection scope of the present invention is not limited in this:
Embodiment 1:
Utilize the Blast database to Yokenella WZY002(CCTCC No:M2013099) 16S rDNA carry out sequence alignment, find out its identical and contiguous genus kind of some bacterial strains, and with Clastal W software analysis, the phylogenetic tree of the Yokenella WZY002 that draws, as shown in Figure 1.(Yokenella regensburgei strain CIP105435) is the most approaching on sibship for Yokenella WZY002 and thunder Allen Ginsberg Yokenella.
Embodiment 2:
Yokenella WZY002(CCTCC No:M2013099) fermention medium is formed: peptone 10g/L, yeast extract 5g/L, NaCl5g/L, solvent are water, pH7.0～7.2,121 ℃ sterilization 20min.
Yokenella WZY002 is inoculated in the 150ml fermention medium, cultivates 12～48 hours under 30 ℃, the condition of shaking speed 200rpm.Fermented liquid is abandoned supernatant liquor behind the centrifugal 10min of 10000rpm, thalline washs once with reaction buffer, and the gained wet thallus is biological catalyst.
Embodiment 3:
Yokenella WZY002 regioselectivity reductase 12-crotonaldehyde (crotonic aldehyde): in the 2mL reaction system, contain the phosphate buffered saline buffer of 100mM pH7.2 respectively, 0.25g Yokenella wet thallus, the crotonic aldehyde of 50mM, the various auxilliary substrate of 500mM.Contrast is not for adding cosubstrate.Reaction is 12 hours under 30 ℃ and 200rpm.
After reaction finishes, add the ethyl acetate of 2mL in the reaction solution, put into shaking table extraction 1 hour under 30 ℃ and 200rpm.Extraction liquid is got organic phase 400～1000 μ L at the centrifugal 10min of 10000rpm, adds excessive anhydrous Na
2SO
4Drying is carried out gas chromatographic analysis to substrate and converted product thereof, and the Virahol of 10 times of concentration of substrate, glycerine, ethanol and glucose can improve 2～22 times of yield.Glucose most pronounced effects is wherein added the glucose of 10 times of concentration of substrate, and the reaction product yield reaches 85.6%, and transformation efficiency reaches 98%.
Embodiment 4:
Yokenella WZY002 regioselectivity reduction crotonic aldehyde: in the 2mL reaction system, the phosphate buffered saline buffer that contains 100mM pH7.2 respectively, 0.25g Yokenella wet thallus, the crotonic aldehyde of 50mM (crotonic aldehyde), glucose concn is 2mol/L, and reaction is 12 hours under 30 ℃ and 200rpm.
After reaction finishes, add the ethyl acetate of 2mL in the reaction solution, put into shaking table extraction 1 hour under 30 ℃ and 200rpm.Extraction liquid is got organic phase 400～1000 μ L at the centrifugal 10min of 10000rpm, adds excessive anhydrous Na
2SO
4Dry, substrate and converted product thereof are carried out gas chromatographic analysis, and efficiency of pcr product is not significantly improved to add glucose when not adding glucose, and glucose addition best results when being 10 times of substrates, efficiency of pcr product reaches 83%, and transformation efficiency also improves and reaches 98%.
Embodiment 5:
In the 2mL reaction system, contain the phosphate buffered saline buffer of 100mM pH7.2 respectively, 0.25g Yokenella wet thallus, the crotonic aldehyde of 50mM, the glucose of 250mM, standing and reacting is 12 hours under differing temps.
After reaction finishes, add the ethyl acetate of 2mL in the reaction solution, put into shaking table extraction 1 hour under 30 ℃ and 200rpm.Extraction liquid is got organic phase 400～1000 μ L at the centrifugal 10min of 10000rpm, adds excessive anhydrous Na
2SO
4Drying is carried out gas chromatographic analysis to substrate and converted product thereof, and the crotonic aldehyde of Yokenella WZY002 has catalysis activity at 4～60 ℃, but the highest at 30 ℃ of vigor, and efficiency of pcr product reaches 83%, and transformation efficiency also improves and reaches 98%.
Embodiment 6:
Damping fluid (phosphate buffered saline buffer, pH6.0～8.9 of in the 2mL reaction system, containing the different pH of 200mM respectively; Glycine-NaOH damping fluid, pH8.9～9.6), 0.25g Yokenella wet thallus, the crotonic aldehyde of 50mM, the glucose of 250mM.Reaction is 4 hours under 30 ℃ and 200rpm.
After reaction finishes, add the ethyl acetate of 2mL in the reaction solution, put into shaking table extraction 1 hour under 30 ℃ and 200rpm.Extraction liquid is got organic phase 400～1000 μ L at the centrifugal 10min of 10000rpm, adds excessive anhydrous Na
2SO
4Drying is carried out gas chromatographic analysis to substrate and converted product thereof, and Yokenella WZY002 has catalysis activity to crotonic aldehyde in pH6～9.5, and vigor is the highest in the phosphate buffered saline buffer of pH8.0, and efficiency of pcr product reaches 83%, and transformation efficiency also improves and reaches 98%.
Embodiment 7:
Yokenella WZY002 regioselectivity reduction α, β-unsaturated olefine aldehydr (ketone): in the 2mL reaction system, the phosphate buffered saline buffer that contains 200mM pH8.0 respectively, 0.25g Yokenella wet thallus, the various α of 50mM, the various ketenes of β-unsaturated olefine aldehydr or 10mM, 250mM glucose reacts under 30 ℃ and 200rpm.
After reaction finishes, add the ethyl acetate of 2mL in the reaction solution, put into shaking table and under 30 ℃ and 200rpm, extracted 1～2 hour.Extraction liquid is got organic phase 400～1000 μ L at the centrifugal 10min of 10000rpm, adds excessive anhydrous Na
2SO
4Drying is carried out gas-chromatography and mass spectrometry analysis to substrate and converted product thereof, and the result is as shown in table 1.
Table 1: Yokenella WZY002 catalytic reduction α, β-unsaturated olefine aldehydr (ketone)
A, selectivity refers to that reaction finishes back purpose product α, beta unsaturated alcohol accounts for the per-cent of total reduzate.
As can be seen from Table 1, Yokenella WZY002 shows higher catalysis activity to most of olefine aldehydrs, and corresponding regioselectivity is also very high, when substrate is crotonic aldehyde, 2-hexenoic aldehyde, 2-methyl-2-pentenals, product yield reaches all more than 94%, and based on α, the regioselectivity that β-unsaturated enol generates is also up to 99%.Than olefine aldehydr, Yokenella WZY002 is lower to all ketenes catalysis activities, but still has good regioselectivity.
Embodiment 8:
Yokenella WZY002 catalytic reduction aromatic aldehyde (ketone): in the 2mL reaction system, the phosphate buffered saline buffer that contains 200mM pH8.0 respectively, 0.25g Yokenella wet thallus, the various aromatic aldehydes of 50mM or the various aromatic ketones of 10mM, 250mM glucose reacts under 30 ℃ and 200rpm.
After reaction finishes, add the ethyl acetate of 2mL in the reaction solution, put into shaking table extraction 1 hour under 30 ℃ and 200rpm.Extraction liquid is got organic phase 400～1000 μ L at the centrifugal 10min of 10000rpm, adds excessive anhydrous Na
2SO
4Drying is carried out gas-chromatography and mass spectrometry analysis to substrate and converted product thereof, and the result is as shown in table 2.
Table 2: Yokenella WZY002 catalytic reduction aromatic aldehyde (ketone)
A, enantio-selectivity are (S)-type.
As can be seen from Table 2, the benzene of Yokenella WZY002 adds aldehyde and Vanillin all has very high catalysis activity, and especially catalysis phenyl aldehyde transformation efficiency reaches 99.6%.With respect to aromatic aldehyde, Yokenella WZY002 is, and the aromatic ketone catalysis activity is lower, but product all has very high enantio-selectivity, and when substrate was the 2-hydroxy acetophenone, product e.e. value reached 99%.
Claims (9)
1. Yokenella (Yokenella sp.) WZY002 is preserved in Chinese typical culture collection center, the address: China, Wuhan, Wuhan University, 430072, deposit number: CCTCC No:M2013099, preservation date: on March 22nd, 2013.
2. the described Yokenella WZY002 of claim 1 reduces α in regioselectivity, β-unsaturated olefine aldehydr or α, and β-unsaturated ketenes prepares α, the application in β-unsaturated enol.
3. application as claimed in claim 3, it is characterized in that described α, β-unsaturated olefine aldehydr or α, β-unsaturated ketenes are one of following: crotonic aldehyde, 2-hexenoic aldehyde, 2-methyl-2-pentenals, 2-octenal, 2-decenal, citral, phenylacrolein, mesityl oxide, jononeionone, 3-octene-2-ketone and 4-methoxyl group-3-butene-2-ketone.
4. the described Yokenella WZY002 of claim 1 prepares application in the chirality aromatic alcohol at the asymmetric reduction aromatic ketone.
5. application as claimed in claim 4 is characterized in that described aromatic ketone is one of following: methyl phenyl ketone, 2-bromoacetophenone, 4-bromoacetophenone, 2-hydroxy acetophenone, benzylideneacetone.
6. the described Yokenella WZY002 of claim 1 prepares application in the aromatic alcohol at the reduction aromatic aldehyde.
7. application as claimed in claim 6 is characterized in that described aromatic aldehyde is phenyl aldehyde or Vanillin.
8. as the described application of claim 2～7, it is characterized in that described application method is as follows: with α, β-unsaturated olefine aldehydr or α, β-unsaturated ketenes or aromatic aldehyde or aromatic ketone are substrate, are biological catalyst with Yokenella WZY002 wet thallus, in the damping fluid of pH6～9, concentration of substrate is 5～200mM, reacted 2～72 hours under 4～60 ℃ and shaking speed 0～200rpm, reaction finishes by ethyl acetate extraction, and the centrifugal organic phase that obtains is reaction product.
9. application as claimed in claim 8, it is characterised in that specifically described Yokenella WZY002 wet thallus makes as follows: fermention medium is formed: peptone 10g/L, yeast extract 5g/L, NaCl5g/L, solvent is water, pH7.0～7.2, Yokenella WZY002 is inoculated in the fermention medium, under 30 ℃, the condition of shaking speed 200rpm, cultivated 12～48 hours, the gained fermented liquid is at the centrifugal 10min of 10000rpm, abandon supernatant liquor, thalline washs once with the damping fluid of pH6～9, and the gained wet thallus is biological catalyst.
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| CN114874956B (en) * | 2022-06-21 | 2023-05-26 | 广西科学院 | Lei Jinsi Baker yolker strain GXAS49-I and application thereof |
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