CN105624217B - A kind of method of microorganism conversion - Google Patents
A kind of method of microorganism conversion Download PDFInfo
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- CN105624217B CN105624217B CN201610085550.7A CN201610085550A CN105624217B CN 105624217 B CN105624217 B CN 105624217B CN 201610085550 A CN201610085550 A CN 201610085550A CN 105624217 B CN105624217 B CN 105624217B
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Abstract
The present invention relates to produce R- (+) -3- (3,4- dihydroxy phenyl) -2 hydroxy propanoic acid using Providence bacterium microorganism conversion levodopa.This method process is simple, has important industrial application value.
Description
Technical field
The present invention produces danshensu using Providence bacterium conversion levodopa, belongs to industrial microorganism field.
Background technique
Danshensu, scientific name R- (+) -3- (3,4- dihydroxy phenyl) -2 hydroxy propanoic acid, D- (+)-β-(3,4- dihydroxy benzenes
Base) lactic acid, English name are as follows: Danshensu, (R)-(+) -3- (3,4-Dihydroxyphenyl)-lactic acid, (R) -
(+) -3- (3,4-Dihydroxyphenyl) -2-hydroxypropanoic acid is a kind of dextrorotation phenolic acid compound.
Danshensu is that important in Salvia miltiorrhiza Bge water extract wants effective ingredient, and the country obtained simultaneously from Salvia miltiorrhiza Bge water extract in 1980
Identify structure (research of Determination of water-soluble active constituents of radix, the structure of II .D (+) β (3,4- dihydroxy phenyl) lactic acid, Shanghai
One medical college's journal, 1980,05 (7), 384-385), it is various research shows that danshensu have important pharmacological effect effect,
Treatment of cardiovascular and cerebrovascular disease etc. has unique treatment effect.
Current danshensu, which is mainly extracted from Radix Salviae Miltiorrhizae, obtains (patent CN200810038853.9).Danshensu is in Radix Salviae Miltiorrhizae
Content is lower, and danshensu planting cost height and limits throughput, therefore not only price is high but also much can not for current danshensu
Meets the needs of market.Patent CN201310559498.0 proposes a kind of building bacillus coli gene engineering drawing and utilizes glucose
The method that fermentation produces danshensu, since metabolic pathway of synthesizing relates to the use of hydroxylase, which is easy to make metabolic process product
The yield of danshensu is aoxidized and influenced, simultaneously because Escherichia coli fermentation is high oxygen process, can also aoxidize danshensu, therefore work as
Preceding this method yield is lower, and cost will be higher than plant extract process.Patent CN201210190171.6 proposes the red phenol of hydrolysis
The method of sour B production danshensu, tanshin polyphenolic acid B need to be extracted from Radix Salviae Miltiorrhizae, and chemical hydrolysis process has a large amount of side reactions, same uncomfortable
For large-scale production.The catalyst of chirality synthesis danshensu (patent CN201210420488.4) is prohibitively expensive, currently also only
Rest on laboratory level.
Significant application value based on danshensu, this patent propose left-handed using the conversion of Providence bacterium microorganism
The scheme of DOPA production danshensu.Levodopa is also named: L-3- (3,4- dihydroxy phenyl) alanine (L-DOPA, L-3,4-
dihydroxyphenylalanine).Current levodopa can produce (Overview from plant extract also microbial fermentation
On the biotechnological production of L-DOPA, 2015, Appl Microbiol Biotechnol,
99:575-584), abundant raw material is easy to get.
Providence bacterium (Providencia) is a kind of gramnegative bacterium that can make phenylalanine oxidative deamination.
Existing main 8 kinds: producing alkali Providence (Providencia alcalifaciens), providencia stuartii
(Providencia stuartii), thunder pole Providence (Providencia rettgeri), pest Providian this
Bacterium (Providencia vermicola), Providencia sneebia, Providencia burhodogranariea.It is general
Luo Weidengsi bacterium has powerful oxidative deamination ability (Sherris Medical Microbiology, 2004,4th ed.),
Then levodopa can be then reduced into danshensu by Providence bacterium oxidative deamination at 3,4- dihydroxyphenyl pyruvic acid.3,
Although 4- dihydroxyphenyl pyruvic acid is more direct substrate, but expensive and unstable, therefore levodopa is optimal
Substrate.Providence bacterium is a kind of facultative anaerobic bacteria, and production danshensu, tool can be converted under anaerobic condition or aerobic condition
There is the characteristics of high conversion and high-purity.
Summary of the invention
The present invention produces danshensu, technical side by culture Providence bacterium microorganism thallus, conversion levodopa
Case is as follows:
1, bacterial strain
Bacterial strain used in the present invention has the Providencia alcalifaciens ATCC purchased from U.S.'s ATCC strain library
9886、Providencia rustigianii ATCC 33673、Providencia sneebia ATCC BAA-1589、
Providencia rettgeri ATCC 29944、Providencia heimbachae ATCC 35613、Providencia
Stuartii ATCC 33672, Providencia burhodogranariea ATCC BAA-1590 and purchased from Chinese work
The Providencia rettgeri CICC 10488 and China typical culture collection of industry Microbiological Culture Collection administrative center
The Providencia vermicola CCTCC AB 205297 at center.
2, thallus culture
Liquid state fermentation culture medium composition are as follows: carbon source 0-50g/L, nitrogen source 0-50g/L, diammonium hydrogen phosphate 0-2g/L, di(2-ethylhexyl)phosphate
PH to 2-8 is adjusted in hydrogen potassium 0-1g/L, magnesium sulfate 0-0.5g/L, ferrous sulfate 0-0.5g/L, common salt 0-5g/L, can also pH
It is natural；Inoculum concentration is 5-20%, and fermentation temperature is 20-40 DEG C, and fermentation period is 24-72 hours.Seed and fermentation are all made of this
Culture medium.
Carbon source for cultivating strain can be glucose, fructose, maltose, xylose, sucrose, galactolipin, glycerol.Culture
It can be the organic nitrogen sources such as ammonium sulfate, ammonium chloride, ammonium nitrate, peptone, yeast extract, urea, corn pulp with nitrogen source.Carbon source and nitrogen
Source can be one or more combinations.
The process of liquid culture thallus can use anaerobism or aerobic mode.
3, conversion produces danshensu
The scheme that conversion process uses has 2 kinds:
(1) the liquid incubation of cell, levodopa substrate is added in above-mentioned cultivating system；Levodopa addition
Amount is 0-3g/L.
(2) liquid state fermentation culture is centrifuged removal fermentation liquid and obtains thallus, thallus is put into containing levodopa substrate
Reactant aqueous solution system in carry out；20-40 DEG C of conversion process temperature, pH 2-8, transformation time 1-24 hours.It is left in conversion fluid
Rotation DOPA initial concentration is 0.1-3g/L.
4, the detection and analysis of sample
Conversion fluid is tested and analyzed using 200 high performance liquid chromatograph of PerkinElmer Series, chromatographic condition are as follows: stream
Dynamic phase is -0.1% formic acid water of methanol (40:60), using Chinese nation Megres C18 chromatographic column (4.6 × 250mm, 5 μm), flow velocity
0.6ml/min, 30 DEG C of column temperature, 20 μ l of sample volume, detector wavelength 280nm.
Using the DAC-HB50 preparation chromatographic column preparation conversion sample of Hanbon Sci. & Tech. Co., Ltd., chromatographic condition is prepared
Are as follows: 50% methanol of mobile phase, column temperature nature, flow velocity 3ml/min, sample volume 5ml.Sample reaches chromatographically pure 99.9%, repeatedly into
The isolated product of sample vacuum rotating at 50 DEG C is evaporated.The sample 0.5g being prepared is weighed, is dissolved in deionized water simultaneously
It is settled to 50ml, the full-automatic polarimeter measurement degree of giving out light of AP-300 of delaying is liked using Japan.Further adopt Varian Gemini
The nuclear magnetic data of 2000 (VnmrS 600MHz, 600/54/ASP) analysis sample.Sample further uses UPLC-QTOF-MS method
Analyzing molecules amount, instrument are Waters MALDI SYNAPT QTOF MS liquid chromatography tandem quadrupole rod time of-flight mass spectrometer.
Specific embodiment
Embodiment 1
The analysis of converted product measures.
It is as follows to prepare culture medium: yeast extract 5g/L, peptone 10g/L, sodium chloride 5g/L.Liquid amount in 500ml triangular flask
For 100ml, totally 50 bottles, 120 DEG C, sterilize within 20 minutes.Take 33673 glycerol tube kind of Providencia rustigianii ATCC
Sub- liquid 1mL inoculation, 30 DEG C of fermentation temperature, shaking speed 200rpm.Culture 24 after, by fermentation liquid centrifugation (revolving speed 10000rpm, when
Between 10min), removal supernatant obtain thallus, be centrifuged the thallus of acquisition with twice of sterile water wash.20g wet thallus is taken to be put into a left side
It revolves in the 1000ml solution that DOPA concentration is 2g/L, is uniformly mixed.After 37 DEG C of shaking tables vibrate (100rpm) 24 hours, 100 DEG C
3 minutes killing thallus of heating water bath.It is centrifuged (revolving speed 10000rpm, time 10min) removal thallus, the supernatant after being converted again
Liquid.Liquid phase analysis danshensu concentration is 1.1g/L, and remaining levodopa concentration is 0.6g/L.0.85g is obtained using preparation chromatography
Sterling.
Polarimeter analyzes its optical activityNuclear magnetic data are as follows: 1H NMR (DMSO-d6,600MHz): δ
8.77 (s, 1H), 6.62 (dd, J=24Hz, 1H), 6.65 (dd, J=12Hz, 1H), 6.46 (dd, J=24Hz, 1H), 5.48
(s,1H),4.06-4.17(m,1H),2.61-2.81(m,1H)；13C NMR(DMSO-d6,600MHz):δ175.3,174.1,
144.9,144.7,143.8,143.6,128.7,128.7,120.4,120.2,117.1,116.8,115.3,115.2,71.5,
71.5,51.6.The mass spectrometric data of converted product are as follows: (- ESI, negative mode) m/z:197.0 [M-1].
According to above data and pertinent literature (Stereochemical configuration of β-(3,4-
dihydroxyphenyl)lactic acid from Rosmarinus officinalis.Ricerea Sci.80:255-
259. [Chem.Abs.54:24520.1960], the research of Determination of water-soluble active constituents of radix, II .D (+) β (3,4- dihydroxy benzenes
Base) lactic acid structure, the first medical college of Shanghai journal, 1980,05 (7), 384-385), determine its molecule and optical texture and day
Right danshensu is completely the same.
Embodiment 2
Aerobic culture is compared with detesting culture.Prepare culture medium: glucose 30g/L, peptone 20g/L, diammonium hydrogen phosphate
1g/L, potassium dihydrogen phosphate 1g/L, magnesium sulfate 0.3g/L, ferrous sulfate 0.3g/L；Originating pH and fermentation process pH is nature
Liquid amount is 100ml in 500ml triangular flask, totally 2 bottles, 120 DEG C, is sterilized within 20 minutes.
29944 glycerol tube seed liquor 1mL of Providencia rettgeri ATCC is taken to be inoculated with 1 bottle, in anaerobic culture box
In 35 DEG C cultivate 72 hours, be centrifuged the thallus of acquisition with twice of sterile water wash.0.1g wet thallus is taken to be put into levodopa concentration
To be uniformly mixed in the 4ml solution of 2g/L, after 35 DEG C of standings convert 24 hours in anaerobic culture box, 100 DEG C of heating water baths 3 divide
Clock kills thallus.It is centrifuged (revolving speed 10000rpm, time 10min) removal thallus, the supernatant after being converted again.Liquid phase analysis
Danshensu concentration is 0.9g/L, and remaining levodopa concentration is 0.7g/L.
29944 glycerol tube seed liquor 1mL of Providencia rettgeri ATCC is taken to be inoculated with 1 bottle, in shaking table
It is cultivated 24 hours for 35 DEG C in (200rpm).Fermentation liquid is centrifuged (revolving speed 10000rpm, time 10min), removal supernatant obtains
Thallus is centrifuged the thallus of acquisition with twice of sterile water wash.0.1g wet thallus is taken to be put into the 4ml that levodopa concentration is 2g/L molten
In liquid, it is uniformly mixed.After 35 DEG C of shaking tables vibrate (100rpm) 12 hours, 100 DEG C of heating water baths, 3 minutes killing thallus.Again from
The heart (revolving speed 10000rpm, time 10min) removes thallus, the supernatant after being converted.Liquid phase analysis danshensu concentration is
1.1g/L, remaining levodopa concentration are 0.3g/L.
Embodiment 3
Culture medium composition are as follows: glucose 1g/L, urea 1g/L, diammonium hydrogen phosphate 1g/L, potassium dihydrogen phosphate 0.1g/L, sulfuric acid
Magnesium 0.1g/L, ferrous sulfate 0.1g/L.Liquid amount is 50ml in 250ml triangular flask, 120 DEG C, is sterilized within 20 minutes.It takes
10488 glycerol tube seed liquor 0.5mL of Providencia rettgeri CICC inoculation, 35 DEG C of fermentation temperature, shaking speed
200rpm.After culture 24, fermentation liquid is centrifuged (revolving speed 10000rpm, time 10min), removal supernatant obtains thallus, centrifugation
The thallus of acquisition is with twice of sterile water wash.0.05g wet thallus is taken to be put into the 2ml solution that levodopa concentration is 0.1g/L,
And pH to 6 is adjusted, it is uniformly mixed.Static conversion 24 hours, filtering with microporous membrane conversion fluid, liquid chromatogram in anaerobic culture box
Danshensu concentration is 0.02g/L in analysis conversion fluid and levodopa residual quantity is 0g/L.
Embodiment 4
Culture medium composition are as follows: fructose 50g/L, ammonium sulfate 5g/L, potassium dihydrogen phosphate 1g/L, magnesium sulfate 0.5g/L, sulfuric acid are sub-
Iron 0.5g/L.Liquid amount is 50ml in 250ml triangular flask, 120 DEG C, is sterilized within 20 minutes.Take Providencia heimbachae
35613 glycerol tube seed liquor 0.5mL of ATCC inoculation, 20 DEG C of fermentation temperature, shaking speed 200rpm.After culture 72, by fermentation liquid
It is centrifuged (revolving speed 10000rpm, time 10min), removal supernatant obtains thallus, is centrifuged the thallus sterile water wash two of acquisition
Time.It takes 0.1g wet thallus to be put into the 2ml solution that levodopa concentration is 2g/L, is uniformly mixed.It is vibrated in 20 DEG C of shaking tables
After (100rpm) 24 hours, filtering with microporous membrane conversion fluid, in liquid-phase chromatographic analysis conversion fluid danshensu concentration be 0.7g/L and
Levodopa residual quantity is 0.8g/L.
Embodiment 5
Culture medium composition are as follows: xylose 50g/L, ammonium sulfate 1g/L, diammonium hydrogen phosphate 1g/L, magnesium sulfate 0.2g/L, sulfuric acid are sub-
Iron 0.1g/L.Liquid amount is 50ml in 250ml triangular flask, 120 DEG C, is sterilized within 20 minutes.Take Providencia vermicola
205297 glycerol tube seed liquor 0.5mL of CCTCC AB inoculation, 40 DEG C of fermentation temperature, shaking speed 200rpm.It, will after culture 48
Fermentation liquid is centrifuged (revolving speed 10000rpm, time 10min), and removal supernatant obtains thallus, is centrifuged the thallus sterile water of acquisition
Twice of cleaning.It takes 0.1g wet thallus to be put into the 2ml solution that levodopa concentration is 2g/L, is uniformly mixed.It shakes in 40 DEG C of shaking tables
After swinging (100rpm) 24 hours, filtering with microporous membrane conversion fluid, danshensu concentration is 0.4g/L in liquid-phase chromatographic analysis conversion fluid
And levodopa residual quantity is 1.2g/L.
Embodiment 6
Culture medium composition are as follows: glycerol 15g/L, ammonium nitrate 1g/L, diammonium hydrogen phosphate 1g/L, potassium dihydrogen phosphate 0.1g/L, sulphur
Sour ferrous iron 0.1g/L.Liquid amount is 50ml in 250ml triangular flask, 120 DEG C, is sterilized within 20 minutes.Take Providencia
205297 glycerol tube seed liquor 0.5mL of vermicola CCTCC AB inoculation, 30 DEG C of fermentation temperature, shaking speed 200rpm.Training
After supporting 24, fermentation liquid is centrifuged (revolving speed 10000rpm, time 10min), removal supernatant obtains thallus, is centrifuged the thallus of acquisition
With twice of sterile water wash.It takes 0.1g wet thallus to be put into the 2ml solution that levodopa concentration is 2g/L, is uniformly mixed.In 20
Static conversion 24 hours in DEG C anaerobic culture box, filtering with microporous membrane conversion fluid, danshensu is dense in liquid-phase chromatographic analysis conversion fluid
Degree is 0.8g/L and levodopa residual quantity is 0.4g/L.
Embodiment 7
Culture medium composition are as follows: maltose 15g/L, ammonium chloride 1g/L, diammonium hydrogen phosphate 1g/L, potassium dihydrogen phosphate 0.1g/L,
Magnesium sulfate 0.1g/L adjusts pH to 5.Liquid amount is 50ml in 250ml triangular flask, 120 DEG C, is sterilized within 20 minutes.It takes
9886 glycerol tube seed liquor 0.5mL of Providencia alcalifaciens ATCC inoculation, 35 DEG C of fermentation temperature, shaking table turns
Fast 200rpm.After culture 24, fermentation liquid is centrifuged (revolving speed 10000rpm, time 10min), removal supernatant obtains thallus, from
The thallus that the heart obtains is with twice of sterile water wash.It takes 0.1g wet thallus to be put into the 2ml solution that levodopa concentration is 3g/L, mixes
It closes uniform.Static conversion 24 hours, filtering with microporous membrane conversion fluid, liquid-phase chromatographic analysis conversion fluid in 40 DEG C of anaerobic culture boxes
Middle danshensu concentration is 0.9g/L and levodopa residual quantity is 1.2g/L.
Embodiment 8
Culture medium composition are as follows: galactolipin 1g/L, urea 1g/L, diammonium hydrogen phosphate 1g/L, potassium dihydrogen phosphate 0.1g/L, sulfuric acid
Magnesium 0.1g/L, ferrous sulfate 0.1g/L adjust pH to 2.Liquid amount is 50ml in 250ml triangular flask, 120 DEG C, is sterilized within 20 minutes.
Providencia sneebia ATCC BAA-1589 glycerol tube seed liquor 0.5mL is taken to be inoculated with, 35 DEG C of fermentation temperature, shaking table turns
Fast 200rpm.After culture 24, fermentation liquid is centrifuged (revolving speed 10000rpm, time 10min), removal supernatant obtains thallus, from
The thallus that the heart obtains is with twice of sterile water wash.0.1g wet thallus is taken to be put into the 2ml solution that levodopa concentration is 2g/L, and
PH to 2 is adjusted, is uniformly mixed.Static conversion 24 hours, filtering with microporous membrane conversion fluid, liquid phase color in 37 DEG C of anaerobic culture boxes
Danshensu concentration is 0.2g/L in spectrum analysis conversion fluid and levodopa residual quantity is 1.2g/L.
Embodiment 9
Culture medium composition are as follows: glucose 1g/L, peptone 1g/L, diammonium hydrogen phosphate 1g/L, potassium dihydrogen phosphate 0.1g/L, sulphur
Sour magnesium 0.1g/L, ferrous sulfate 0.1g/L, levodopa 2g/L adjust pH to 8.In 250ml triangular flask liquid amount be 50ml, 120
DEG C, it sterilizes within 20 minutes.33672 glycerol tube seed liquor 0.5mL of Providencia stuartii ATCC is taken to be inoculated with, fermentation temperature
35 DEG C, shaking speed 200rpm.After culture 24, filtering with microporous membrane conversion fluid, danshensu is dense in liquid-phase chromatographic analysis conversion fluid
Degree is 1.1g/L and levodopa residual quantity is 0.3g/L.
Embodiment 10
Culture medium composition are as follows: glucose 1g/L, urea 1g/L, diammonium hydrogen phosphate 1g/L, potassium dihydrogen phosphate 0.1g/L, sulfuric acid
Magnesium 0.1g/L, ferrous sulfate 0.1g/L adjust pH to 8.Liquid amount is 100ml in 500ml triangular flask, 120 DEG C, is gone out within 20 minutes
Bacterium, totally 10 bottles.Providencia burhodogranariea ATCC BAA-1590 glycerol tube seed liquor 0.5mL is respectively taken to connect
Kind, 35 DEG C of fermentation temperature, shaking speed 200rpm.After culture 24, fermentation liquid is centrifuged (revolving speed 10000rpm, time 10min),
It removes supernatant and obtains thallus, be centrifuged the thallus of acquisition with twice of sterile water wash.5g wet thallus is taken to be put into levodopa concentration
For in the 10ml solution of 3g/L, and pH to 5 is adjusted, is uniformly mixed.After 35 DEG C of shaking tables vibrate (100rpm) 1 hour, micropore filter
Film filters conversion fluid, and danshensu concentration is 1.9g/L in liquid-phase chromatographic analysis conversion fluid and levodopa residual quantity is 0.4g/L.
Embodiment 11
Culture medium composition are as follows: glucose 10g/L, peptone 1g/L, diammonium hydrogen phosphate 1g/L, potassium dihydrogen phosphate 0.1g/L,
Magnesium sulfate 0.1g/L, ferrous sulfate 0.1g/L, pH to 5.Liquid amount is 50ml in 250ml triangular flask, 120 DEG C, is sterilized within 20 minutes.
9886 glycerol tube seed liquor 0.5mL of Providencia alcalifaciens ATCC is taken to be inoculated with, 35 DEG C of fermentation temperature, shaking table
Revolving speed 200rpm.After culture 24, filtering with microporous membrane conversion fluid, danshensu concentration is 0.03g/ in liquid-phase chromatographic analysis conversion fluid
L and levodopa content are 0.02g/L.
Claims (4)
1. a kind of method of conversion levodopa production R- (+) -3- (3,4- dihydroxy phenyl) -2 hydroxy propanoic acid, feature exist
In the method is to carry out conversion production using Providence bacterium microorganism；The Providence bacterium microorganism has:
Produce alkali Providence, providencia stuartii, thunder pole Providence, pest Providence,
Providencia sneebia and Providencia burhodogranariea.
2. the method according to claim 1, wherein the incubation energy of the Providence bacterium microorganism
It is enough also to be carried out in aerobic state in anaerobic state.
3. according to the method described in claim 2, it is characterized in that, the obtained thallus of culture, conversion levodopa can be
Anaerobic state can also be carried out in aerobic state.
4. according to the method described in claim 2, it is characterized in that, levodopa side can be directly added into thallus incubation
Long thallus side conversion production R- (+) -3- (3,4- dihydroxy phenyl) -2 hydroxy propanoic acid.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102876737A (en) * | 2012-09-13 | 2013-01-16 | 江苏梁丰食品集团有限公司 | Method for catalyzing and synthetising enzyme of D-benzene lactic acid |
| CN103013847A (en) * | 2012-07-10 | 2013-04-03 | 北京科技大学 | Ammonia-producing mineral leaching bacterium JAT-1 as well as culture method and application of ammonia-producing mineral leaching bacterium JAT-1 |
| CN104878024A (en) * | 2015-05-27 | 2015-09-02 | 常熟理工学院 | Recombinant Escherichia coli construction and (S)-2-hydroxy-3-phenylpropionic acid synthesis method |
| CN105039434A (en) * | 2015-09-08 | 2015-11-11 | 浙江工业大学 | Method for conversion and synthesis of phenyllactic acid by using microorganisms |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103013847A (en) * | 2012-07-10 | 2013-04-03 | 北京科技大学 | Ammonia-producing mineral leaching bacterium JAT-1 as well as culture method and application of ammonia-producing mineral leaching bacterium JAT-1 |
| CN102876737A (en) * | 2012-09-13 | 2013-01-16 | 江苏梁丰食品集团有限公司 | Method for catalyzing and synthetising enzyme of D-benzene lactic acid |
| CN104878024A (en) * | 2015-05-27 | 2015-09-02 | 常熟理工学院 | Recombinant Escherichia coli construction and (S)-2-hydroxy-3-phenylpropionic acid synthesis method |
| CN105039434A (en) * | 2015-09-08 | 2015-11-11 | 浙江工业大学 | Method for conversion and synthesis of phenyllactic acid by using microorganisms |
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