CN103289922B - Yokenella and the application in preparation α, β-unsaturated enol and aromatic alcohol thereof - Google Patents
Yokenella and the application in preparation α, β-unsaturated enol and aromatic alcohol thereof Download PDFInfo
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Abstract
The invention provides a strain new strains---Yokenella (Yokenella sp.) WZY002, and prepare α at regioselective reduction α, β-unsaturated olefine aldehydr (ketone), the application in aromatic alcohol is prepared in β-unsaturated enol and reduction aromatic aldehyde (ketone).This bacterial strain is preserved in China typical culture collection center, address: China, Wuhan, Wuhan University, 430072, deposit number: CCTCC No:M2013099, preservation date: on March 22nd, 2013.Beneficial effect of the present invention is mainly reflected in: provide the new strains that a strain has high regioselectivity, highly-solid selectively and high enzymatic activity, this bacterial strain catalysis α, the regioselective reduction of β-unsaturated olefine aldehydr (ketone) can obtain multiple α, β-unsaturated enol, this bacterial strain also the reduction of catalysis aromatic aldehyde (ketone) can obtain aromatic alcohol simultaneously.Bacterial strain of the present invention as biological catalyst, regioselectivity and stereoselectivity high, catalytic activity is strong, and the reaction of institute's catalysis does not need to add coenzyme, and reaction conditions is gentle, and suitability for industrialized production has higher using value.
Description
(1) technical field
The present invention relates to a strain new strains---Yokenella (Yokenella sp.) WZY002, and at regioselective reduction α, β-unsaturated olefine aldehydr or α, β-Unsaturated Alkenone prepares α, application in β-unsaturated enol, asymmetric reduction aromatic ketone prepares chiral aromatic alcohols, and reduction aromatic aldehyde prepares the application in aromatic alcohol.
(2) background technology
α, β-unsaturated enol is very important organic synthesis (drug containing synthesis) intermediate, as styryl carbinol, lemon alcohol, crotyl alcohol etc. are widely used in spices, medicine and other fine chemicals are produced, be often used as food using additive, fragrance blender and medicine intermediate etc., there is higher economic worth.
The selective hydrogenation of α, β-unsaturated olefine aldehydr (ketone) is the committed step of synthetic perfume, medicine intermediate etc.Because thermodynamically C=C key is lower than the activation energy of C=O key, kinetically C=C key is more active than C=O key, and under the effect of generalization chemical catalyst, α, the primary product of β-unsaturated olefine aldehydr (ketone) mostly is saturated aldehyde (ketone), the yield of more valuable product α, β-unsaturated enol is lower.With chemical catalyst unlike, biological catalyst has more excellent regioselectivity, only can obtain corresponding α, β-unsaturated enol to the C=O key selective hydrogenation of α, β-unsaturated olefine aldehydr (ketone).The reaction conditions of biological catalyst is gentle, stereoselectivity is high, environmental friendliness, be easy to Separation and Recovery and the deficiency of advantage also the compensate for chemical catalyst such as production cost is low.At present, biological catalysis prepares α, and β-unsaturated enol is mainly realized by selective reduction α, β-unsaturated olefine aldehydr (ketone).But have not yet to see and utilize Yokenella microorganism catalysis to prepare α, 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 the application in α, β-unsaturated enol and aromatic alcohol Biological preparation thereof.This bacterial strain reducible α, β-unsaturated olefine aldehydr (ketone) obtains α, β-unsaturated enol, also obtains chiral aromatic alcohols by asymmetric reduction aromatic ketone, and also reducible aromatic aldehyde obtains aromatic alcohol.Reaction specificity is strong, and selectivity is good, and vigor is high, and reaction does not need additional coenzyme.
The technical solution used in the present invention is:
Yokenella (Yokenella sp.) WZY002, is preserved in China typical culture collection center, 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 soil sample used respectively from Shandong, Hubei, the ground collection such as Inner Mongol.Yokenella WZY002 screens the vegetable soil from Jianli County, Jingzhou City of Hubei China province.
Dull and stereotyped primary dcreening operation: take the sterilized water that 0.5g soil sample adds 1mL, shake up, leaves standstill, supernatant liquor sterilized water dilutes 1000 times, then gets its 100 μ L applying solid dull and stereotyped, places 3 ~ 5 minutes, draw 100 μ L2-butenols (crotyl alcohol) and be again coated with above-mentioned flat board, be inverted incubated overnight for 30 DEG C.Single bacterium colony that picking grows is transferred in solid test tube slant, 30 DEG C of incubated overnight.The component of solid medium: peptone 1%, yeast extract 0.5%, NaCl0.5%, agar 2%, pH7.0 ~ 7.2,121 DEG C of sterilizing 20min.Substratum composition of the present invention all represents with quality volume percent (W/V), as certain concentration of component 1% represents in 100mL substratum containing this component of 1g.
By inclined-plane inoculation to fermention medium, its component is as follows: peptone 1%, yeast extract 0.5%, NaCl0.5%, pH7.0 ~ 7.2,121 DEG C of sterilizing 20min.30 DEG C of shaking speed 200rpm cultivate 24 ~ 48 hours, obtain thalline and be suspended in buffer solution system after centrifugal.
The wet thallus obtained according to the method described above, be suspended in buffer solution system, add α, beta-unsaturated aldehyde (ketone) or aromatic aldehyde (ketone) react, react after 1 ~ 72 hour, with Chiral gas chromatography or GC-MS analysis substrate and its converted product.
The invention still further relates to the α of described Yokenella WZY002 at regioselective reduction, β-unsaturated olefine aldehydr (ketone) prepares α, the application in β-unsaturated enol.
Preferably, described α, β-unsaturated olefine aldehydr (ketone) is for one of following: crotonic aldehyde, 2-hexenoic aldehyde, 2-methyl-2-pentenal serving, 2-octenal, 2-decenal, citral, phenylacrolein, mesityl oxide, jononeionone, 3-octene-2-ketone and 4-methoxyl group-3-butene-2-one.
The invention still further relates to described Yokenella WZY002 and prepare application in chiral aromatic alcohols at 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 aromatic alcohol at reduction aromatic aldehyde.
Preferably, described aromatic aldehyde is phenyl aldehyde or Vanillin.
Described α, the regioselective 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 dibasic-phosphate sodium dihydrogen buffer solution or pH8.0 ~ 9.0Tris-HCl damping fluid.
The regioselective reduction of described α, β-unsaturated olefine aldehydr (ketone) and the reduction of aromatic aldehyde (ketone) are carried out under glucose, ethanol, glycerine or Virahol exist.
Concrete, described reaction is: with α, β-unsaturated olefine aldehydr (ketone) or aromatic aldehyde (ketone) are substrate, with Yokenella WZY002 wet thallus for catalyzer, in the damping fluid of pH6 ~ 9, concentration of substrate 5 ~ 200mM, react 2 ~ 72 hours under 4 ~ 60 DEG C and shaking speed 0 ~ 200rpm, through extraction into ethyl acetate after reaction terminates, centrifugally obtain organic phase, after anhydrous sodium sulfate drying, Gas-phase acidity and Chiral gas chromatography analysis are carried out to the substrate in organic phase and converted product thereof.Wet thallus is 45 ~ 450g/L relative to the addition of described damping fluid.
Concrete, described Yokenella WZY002 wet thallus can obtain as follows: fermention medium forms: peptone 10g/L, yeast extract 5g/L, NaCl5g/L, solvent is water, pH7.0 ~ 7.2, are inoculated in fermention medium by Yokenella WZY002, in 30 DEG C, cultivate 12 ~ 48 hours under the condition of shaking speed 200rpm, gained fermented liquid is at the centrifugal 10min of 10000rpm, abandon supernatant liquor, once, gained wet thallus is biological catalyst to the buffer solution of thalline pH6 ~ 9.
Beneficial effect of the present invention is mainly reflected in: provide the bacterial strain that a strain has 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 as biological catalyst, regioselectivity and stereoselectivity high, catalytic activity is strong, and the reaction of institute's catalysis does not need to add coenzyme, and reaction conditions is gentle, and suitability for industrialized production has higher using value.
(4) accompanying drawing explanation
Fig. 1 is Yokenella WZY002 phylogenetic tree.
(5) embodiment
Below in conjunction with specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in this:
Embodiment 1:
Utilize 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 strain, and with Clastal W software analysis, draw the phylogenetic tree of Yokenella WZY002, as shown in Figure 1.Yokenella WZY002 and thunder Allen Ginsberg Yokenella (Yokenella regensburgei strain CIP105435) closest in sibship.
Embodiment 2:
Yokenella WZY002(CCTCC No:M2013099) fermention medium composition: peptone 10g/L, yeast extract 5g/L, NaCl5g/L, solvent is water, pH7.0 ~ 7.2,121 DEG C of sterilizing 20min.
Yokenella WZY002 is inoculated in 150ml fermention medium, in 30 DEG C, cultivate 12 ~ 48 hours under the condition of shaking speed 200rpm.Fermented liquid, after the centrifugal 10min of 10000rpm, abandons supernatant liquor, and thalline reaction buffer washs once, and gained wet thallus is biological catalyst.
Embodiment 3:
Yokenella WZY002 regioselective reduction crotonic aldehyde (crotonic aldehyde): in 2mL reaction system, the phosphate buffered saline buffer respectively containing 100mM pH7.2,0.25g Yokenella wet thallus, the crotonic aldehyde of 50mM, the various auxiliary substrate of 500mM.Contrast is not for add cosubstrate.Reaction 12 hours under 30 DEG C and 200rpm.
After reaction terminates, in reaction solution, add the ethyl acetate of 2mL, put into shaking table and extract 1 hour under 30 DEG C and 200rpm.Extraction liquid, at the centrifugal 10min of 10000rpm, is got organic phase 400 ~ 1000 μ L, is added excessive anhydrous Na
2sO
4drying, carries out gas chromatographic analysis to substrate and converted product thereof, and the Virahol of 10 times of concentration of substrate, glycerine, second alcohol and glucose can improve yield 2 ~ 22 times.Wherein glucose most pronounced effects, add the glucose of 10 times of concentration of substrate, reaction product yield reaches 85.6%, and transformation efficiency reaches 98%.
Embodiment 4:
Yokenella WZY002 regioselective reduction crotonic aldehyde: in 2mL reaction system, phosphate buffered saline buffer respectively containing 100mM pH7.2,0.25g Yokenella wet thallus, the crotonic aldehyde (crotonic aldehyde) of 50mM, glucose concn is 2mol/L, reaction 12 hours under 30 DEG C and 200rpm.
After reaction terminates, in reaction solution, add the ethyl acetate of 2mL, put into shaking table and extract 1 hour under 30 DEG C and 200rpm.Extraction liquid, at the centrifugal 10min of 10000rpm, is got organic phase 400 ~ 1000 μ L, is added excessive anhydrous Na
2sO
4dry, gas chromatographic analysis is carried out to substrate and converted product thereof, adds glucose ratio and efficiency of pcr product when not adding glucose to be significantly improved, and best results when glucose addition is substrate 10 times, efficiency of pcr product reaches 83%, and transformation efficiency also improves and reaches 98%.
Embodiment 5:
In 2mL reaction system, the phosphate buffered saline buffer respectively containing 100mM pH7.2,0.25g Yokenella wet thallus, the crotonic aldehyde of 50mM, the glucose of 250mM, at different temperatures standing and reacting 12 hours.
After reaction terminates, in reaction solution, add the ethyl acetate of 2mL, put into shaking table and extract 1 hour under 30 DEG C and 200rpm.Extraction liquid, at the centrifugal 10min of 10000rpm, is got organic phase 400 ~ 1000 μ L, is added excessive anhydrous Na
2sO
4drying, carry out gas chromatographic analysis to substrate and converted product thereof, Yokenella WZY002 has catalysis activity to crotonic aldehyde at 4 ~ 60 DEG C, but the highest at 30 DEG C 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 respectively containing the different pH of 200mM in 2mL reaction system; Glycine-NaOH buffer, pH8.9 ~ 9.6), 0.25g Yokenella wet thallus, the crotonic aldehyde of 50mM, the glucose of 250mM.Reaction 4 hours under 30 DEG C and 200rpm.
After reaction terminates, in reaction solution, add the ethyl acetate of 2mL, put into shaking table and extract 1 hour under 30 DEG C and 200rpm.Extraction liquid, at the centrifugal 10min of 10000rpm, is got organic phase 400 ~ 1000 μ L, is added excessive anhydrous Na
2sO
4drying, carry out gas chromatographic analysis to substrate and converted product thereof, Yokenella WZY002 has catalysis activity to crotonic aldehyde in pH6 ~ 9.5, and in the phosphate buffered saline buffer of pH8.0, vigor is the highest, and efficiency of pcr product reaches 83%, and transformation efficiency also improves and reaches 98%.
Embodiment 7:
Yokenella WZY002 regioselective reduction α, β-unsaturated olefine aldehydr (ketone): in 2mL reaction system, phosphate buffered saline buffer respectively containing 200mM pH8.0,0.25g Yokenella wet thallus, the various α of 50mM, the various ketenes of β-unsaturated olefine aldehydr or 10mM, 250mM glucose, reacts under 30 DEG C and 200rpm.
After reaction terminates, in reaction solution, add the ethyl acetate of 2mL, put into shaking table and extract 1 ~ 2 hour under 30 DEG C and 200rpm.Extraction liquid, at the centrifugal 10min of 10000rpm, is got organic phase 400 ~ 1000 μ L, is added excessive anhydrous Na
2sO
4drying, carry out gas-chromatography and mass spectrometry analysis to substrate and converted product thereof, 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 terminates rear object product α, and 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 aldehydr, and corresponding regioselectivity is also very high, when substrate is crotonic aldehyde, 2-hexenoic aldehyde, 2-methyl-2-pentenal serving, product yield reaches all more than 94%, and the regioselectivity generated based on α, β-unsaturated enol is also up to 99%.Compared to olefine aldehydr, Yokenella WZY002 is lower to all ketenes catalysis activities, but still has excellent regioselectivity.
Embodiment 8:
Yokenella WZY002 catalytic reduction aromatic aldehyde (ketone): in 2mL reaction system, phosphate buffered saline buffer respectively containing 200mM pH8.0,0.25g Yokenella wet thallus, the various aromatic aldehyde of 50mM or the various aromatic ketones of 10mM, 250mM glucose, reacts under 30 DEG C and 200rpm.
After reaction terminates, in reaction solution, add the ethyl acetate of 2mL, put into shaking table and extract 1 hour under 30 DEG C and 200rpm.Extraction liquid, at the centrifugal 10min of 10000rpm, is got organic phase 400 ~ 1000 μ L, is added excessive anhydrous Na
2sO
4drying, carry out gas-chromatography and mass spectrometry analysis to substrate and converted product thereof, result is as shown in table 2.
Table 2: Yokenella WZY002 catalytic reduction aromatic aldehyde (ketone)
A, enantio-selectivity is (S)-type.
As can be seen from Table 2, Yokenella WZY002 adds aldehyde to benzene and Vanillin all has very high catalysis activity, and especially catalysis phenyl aldehyde transformation efficiency reaches 99.6%.Relative to aromatic aldehyde, Yokenella WZY002 is lower to aromatic ketone catalysis activity, but product all has very high enantio-selectivity, and when substrate is 2-hydroxy acetophenone, product e.e. value reaches 99%.
Claims (10)
1. a Yokenella WZY002 is at regioselective reduction α, β-unsaturated olefine aldehydr or α, β-Unsaturated Alkenone prepare α, the application in β-unsaturated enol, described Yokenella (Yokenella sp.) WZY002, be preserved in China typical culture collection center, address: China, Wuhan, Wuhan University, 430072, deposit number: CCTCC No:M 2013099, preservation date: on March 22nd, 2013.
2. apply as claimed in claim 1, it is characterized in that described α, β-unsaturated olefine aldehydr or α, β-Unsaturated Alkenone are one of following: crotonic aldehyde, 2-hexenoic aldehyde, 2-methyl-2-pentenal serving, 2-octenal, 2-decenal, citral, phenylacrolein, mesityl oxide, jononeionone, 3-octene-2-ketone and 4-methoxyl group-3-butene-2-one.
3. apply as claimed in claim 1, it is characterized in that described application method is as follows: with α, β-unsaturated olefine aldehydr or α, β-Unsaturated Alkenone is substrate, with Yokenella WZY002 wet thallus for biological catalyst, in the damping fluid of pH6 ~ 9, concentration of substrate is 5 ~ 200mM, react 2 ~ 72 hours under 4 ~ 60 DEG C and shaking speed 0 ~ 200rpm, through extraction into ethyl acetate after reaction terminates, the centrifugal organic phase that obtains is reaction product.
4. apply as claimed in claim 3, its specific features is that described Yokenella WZY002 wet thallus obtains as follows: fermention medium forms: peptone 10g/L, yeast extract 5g/L, NaCl 5g/L, solvent is water, pH7.0 ~ 7.2, Yokenella WZY002 is inoculated in fermention medium, in 30 DEG C, cultivate 12 ~ 48 hours under the condition of shaking speed 200rpm, gained fermented liquid is at the centrifugal 10min of 10000rpm, abandon supernatant liquor, once, gained wet thallus is biological catalyst to the buffer solution of thalline pH6 ~ 9.
5. a Yokenella WZY002 prepares the application in chiral aromatic alcohols at asymmetric reduction aromatic ketone, described Yokenella WZY002, be preserved in China typical culture collection center, address: China, Wuhan, Wuhan University, 430072, deposit number: CCTCC No:M 2013099, preservation date: on March 22nd, 2013.
6. apply as claimed in claim 5, it is characterized in that described aromatic ketone is one of following: methyl phenyl ketone, 2-bromoacetophenone, 4-bromoacetophenone, 2-hydroxy acetophenone, benzylideneacetone.
7. apply as claimed in claim 5, it is characterized in that described application method is as follows: take aromatic ketone as substrate, with Yokenella WZY002 wet thallus for biological catalyst, in the damping fluid of pH6 ~ 9, concentration of substrate is 5 ~ 200mM, react 2 ~ 72 hours under 4 ~ 60 DEG C and shaking speed 0 ~ 200rpm, through extraction into ethyl acetate after reaction terminates, the centrifugal organic phase that obtains is reaction product.
8. a Yokenella WZY002 prepares the application in aromatic alcohol at reduction aromatic aldehyde, described Yokenella WZY002, be preserved in China typical culture collection center, address: China, Wuhan, Wuhan University, 430072, deposit number: CCTCC No:M 2013099, preservation date: on March 22nd, 2013.
9. apply as claimed in claim 8, it is characterized in that described aromatic aldehyde is phenyl aldehyde or Vanillin.
10. apply as claimed in claim 8, it is characterized in that described application method is as follows: take aromatic aldehyde as substrate, with Yokenella WZY002 wet thallus for biological catalyst, in the damping fluid of pH6 ~ 9, concentration of substrate is 5 ~ 200mM, react 2 ~ 72 hours under 4 ~ 60 DEG C and shaking speed 0 ~ 200rpm, through extraction into ethyl acetate after reaction terminates, the centrifugal organic phase that obtains is reaction product.
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| CN101528937A (en) * | 2006-11-15 | 2009-09-09 | 巴斯夫欧洲公司 | Process for enzymatic reduction of alkene derivatives |
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