CN105603006B - A kind of method of microorganism conversion - Google Patents
A kind of method of microorganism conversion Download PDFInfo
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- CN105603006B CN105603006B CN201610085601.6A CN201610085601A CN105603006B CN 105603006 B CN105603006 B CN 105603006B CN 201610085601 A CN201610085601 A CN 201610085601A CN 105603006 B CN105603006 B CN 105603006B
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Abstract
The present invention relates to produce R- (+) -3- (4- hydroxy phenyl) -2 hydroxy propanoic acid using Providence bacterium microorganism conversion l-tyrosine.This method process is simple, has important industrial application value.
Description
Technical field
The present invention produces D-4- hydroxyphenyl lactic acid using Providence bacterium conversion l-tyrosine, belongs to industrial microorganism neck
Domain.
Background technique
D-4- hydroxyphenyl lactic acid also known as para hydroxybenzene lactic acid, scientific name are R- (+) -3- (4- hydroxy phenyl) -2- hydroxyl third
Acid, English name are as follows: D-4-hydroxyphenyllactic acid, D-p-Hydroxyphenyllactic acid, R- (+)-
2-hydroxy-3-(4-hydroxyphenyl)propanoic acid。
4- hydroxyphenyl lactic acid is the biology of another wide spectrum in addition to phenyllactic acid generated in lactic acid bacteria fermentation process, low toxicity
Preservative, it is current mainly to pass through lactic acid bacteria generation (Chinese patent CN200810244053.2).4- hydroxyphenyl lactic acid is lactic acid bacteria
The biological preservative of another wide spectrum in addition to phenyllactic acid, low toxicity that are generated in fermentation process, it is current main raw by lactic acid bacteria
At (Chinese patent CN200810244053.2).Have also document show proteus vulgaris (Proteus vulgaris) can will
L-tyrosine is converted to D-4- hydroxyphenyl lactic acid (The influence of conditions of bacterial
cleavage of proteins on the cleavage products,1917,J.Biol.Chem.527-532)。
Based on the significant application value of D-4- hydroxyphenyl lactic acid, this patent proposes the conversion of Providence bacterium microorganism
The scheme of l-tyrosine production D-4- hydroxyphenyl lactic acid.For l-tyrosine currently mainly by Production by Microorganism Fermentation, raw material is rich
Richness 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 l-tyrosine can be then reduced into D-4- hydroxy benzenes cream by Providence bacterium oxidative deamination at 4- hydroxyphenyl pyruvate
Acid.Although 4- hydroxyphenyl pyruvate is more direct substrate, but expensive and unstable, therefore l-tyrosine is optimal
Substrate.Providence bacterium is a kind of facultative anaerobic bacteria, and production D-4- hydroxyl can be converted under anaerobic condition or aerobic condition
Phenyllactic acid has the characteristics that high conversion and high-purity.
Summary of the invention
The present invention passes through culture Providence bacterium microorganism thallus, conversion l-tyrosine production D-4- hydroxy benzenes cream
Acid, technical solution are 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 ATCC35613、Providencia
Stuartii ATCC 33672, Providencia burhodogranariea ATCC BAA-1590 and purchased from Chinese work
The Providencia rettgeriCICC 10488 and China typical culture collection of industry Microbiological Culture Collection administrative center
The Providencia vermicola CCTCC AB205297 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 D-4- hydroxyphenyl lactic acid
The scheme that conversion process uses has 2 kinds:
(1) the liquid incubation of cell, l-tyrosine substrate is added in above-mentioned cultivating system；L-tyrosine addition
Amount is 0-0.3g/L.
(2) liquid state fermentation culture is centrifuged removal fermentation liquid and obtains thallus, thallus is put into containing l-tyrosine substrate
Reactant aqueous solution system in carry out；20-40 DEG C of conversion process temperature, pH 2-8, transformation time 1-24 hours.L- in conversion fluid
Tyrosine initial concentration is 0.1-0.3g/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 200nm.
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 methanol and fixed
Hold 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 2000
The nuclear magnetic data of (VnmrS 600MHz, 600/54/ASP) analysis sample.Sample further uses UPLC-QTOF-MS method to analyze
Molecular weight, 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 L-
Tyrosine concentration is to be uniformly mixed in the 10000ml solution of 0.3g/L.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 again, it is upper after being converted
Clear liquid.Liquid phase analysis D-4- hydroxyphenyl lactic acid concentration is 0.15g/L, and remaining l-tyrosine concentration is 0.11g/L.Using preparing color
Spectrum obtains 0.9g sterling.
Polarimeter analyzes its optical activityNuclear magnetic data are as follows: 1H NMR (acetone-d6, D2O,
600MHz): δ 7.04 (1H, d, J=8.0Hz), 7.03 (1H, d, J=8.0Hz), 6.67 (1H, d, J=8.0), 6.64 (2H, d,
J=8.0Hz), 4.23 (2H, dd, J=4.0,8.0Hz), 2.96 (2H, dd, J=4.0,8.0Hz), 2.74 (1H, dd, J=
8.0Hz)；13C N4MR(acetone-d6,D2O, 600MHz): δ 173.12,155.86,130.46,128.27,130.42,
114.84,114.85,71.52,39.3.The mass spectrometric data of converted product are as follows: (- ESI, negative mode) m/z:181.0
[M-1]。
According to above data, determine that its molecule and optical texture and D-4- hydroxyphenyl lactic acid are 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 l-tyrosine concentration
To be uniformly mixed in the 4ml solution of 0.2g/L, after 35 DEG C of standings convert 24 hours in anaerobic culture box, 100 DEG C of heating water baths 3
Minute kills thallus.It is centrifuged (revolving speed 10000rpm, time 10min) removal thallus, the supernatant after being converted again.Liquid phase point
Analysis D-4- hydroxyphenyl lactic acid concentration is 0.03g/L, and remaining l-tyrosine concentration is 0.11g/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 l-tyrosine concentration is 0.2g/L
In solution, 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
It is centrifuged (revolving speed 10000rpm, time 10min) and removes thallus, the supernatant after being converted.Liquid phase analysis D-4- hydroxy benzenes cream
Acid concentration is 0.04g/L, and remaining l-tyrosine concentration is 0.1g/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 l-tyrosine 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
Analyzing D-4- hydroxyphenyl lactic acid concentration in conversion fluid is 0.02g/L.
Embodiment 4
Culture medium composition are as follows: fructose 50g/L, ammonium sulfate 5g/L, diammonium hydrogen phosphate 1g/L, potassium dihydrogen phosphate 1g/L, sulfuric acid
Magnesium 0.5g/L, ferrous sulfate 0.5g/L.Liquid amount is 50ml in 250ml triangular flask, 120 DEG C, is sterilized within 20 minutes.It takes
35613 glycerol tube seed liquor 0.5mL of Providencia heimbachae ATCC inoculation, 20 DEG C of fermentation temperature, shaking speed
200rpm.After culture 72, 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.It takes 0.1g wet thallus to be put into the 2ml solution that l-tyrosine concentration is 0.2g/L, mixes
It closes uniform.After 20 DEG C of shaking tables oscillation (100rpm) 24 hours, filtering with microporous membrane conversion fluid, in liquid-phase chromatographic analysis conversion fluid
D-4- hydroxyphenyl lactic acid concentration is 0.03g/L and l-tyrosine residual quantity is 0.08g/L.
Embodiment 5
Culture medium composition are as follows: xylose 50g/L, ammonium sulfate 1g/L, potassium dihydrogen 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 l-tyrosine concentration is 0.2g/L, is uniformly mixed.In 40 DEG C of shaking tables
Oscillation (100rpm) is after 24 hours, filtering with microporous membrane conversion fluid, and D-4- hydroxyphenyl lactic acid is dense in liquid-phase chromatographic analysis conversion fluid
Degree is 0.04g/L and l-tyrosine residual quantity is 0.11g/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 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
205297 glycerol tube seed liquor 0.5mL of Providencia vermicola CCTCC AB inoculation, 30 DEG C of fermentation temperature, shaking table
Revolving speed 200rpm.After culture 24, fermentation liquid is centrifuged (revolving speed 10000rpm, time 10min), removal supernatant obtains thallus,
The thallus obtained is centrifuged with twice of sterile water wash.0.1g wet thallus is taken to be put into the 2ml solution that l-tyrosine concentration is 0.2g/L
In, it is uniformly mixed.Static conversion 24 hours, filtering with microporous membrane conversion fluid, liquid-phase chromatographic analysis in 20 DEG C of anaerobic culture boxes
D-4- hydroxyphenyl lactic acid concentration is 0.04g/L in conversion fluid and l-tyrosine residual quantity is 0.09g/L.
Embodiment 7
Culture medium composition are as follows: maltose 15g/L, ammonium chloride 1g/L, diammonium hydrogen phosphate 1g/L, magnesium sulfate 0.1g/L, sulfuric acid
Ferrous 0.1g/L adjusts pH to 5.Liquid amount is 50ml in 250ml triangular flask, 120 DEG C, is sterilized within 20 minutes.Take Providencia
9886 glycerol tube seed liquor 0.5mL of alcalifaciens ATCC inoculation, 35 DEG C of fermentation temperature, shaking speed 200rpm.Culture
After 24, fermentation liquid is centrifuged (revolving speed 10000rpm, time 10min), removal supernatant obtains thallus, and the thallus for being centrifuged acquisition is used
Twice of sterile water wash.It takes 0.1g wet thallus to be put into the 2ml solution that l-tyrosine concentration is 0.3g/L, is uniformly mixed.In 40
Static conversion 24 hours in DEG C anaerobic culture box, filtering with microporous membrane conversion fluid, D-4- hydroxyl in liquid-phase chromatographic analysis conversion fluid
Phenyllactic acid concentration is 0.05g/L and l-tyrosine residual quantity is 0.1g/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 l-tyrosine concentration is 0.2g/L,
And pH to 2 is adjusted, it is uniformly mixed.Static conversion 24 hours, filtering with microporous membrane conversion fluid, liquid phase in 37 DEG C of anaerobic culture boxes
D-4- hydroxyphenyl lactic acid concentration is 0.02g/L in chromatography conversion fluid and l-tyrosine residual quantity is 0.12g/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 ferrous iron 0.1g/L, l-tyrosine 0.2g/L adjust pH to 8.Liquid amount is 50ml in 250ml triangular flask, 120 DEG C, is gone out within 20 minutes
Bacterium.33672 glycerol tube seed liquor 0.5mL of Providencia stuartii ATCC is taken to be inoculated with, 35 DEG C of fermentation temperature, shaking table turns
Fast 200rpm.After culture 24, filtering with microporous membrane conversion fluid, D-4- hydroxyphenyl lactic acid concentration is in liquid-phase chromatographic analysis conversion fluid
0.01g/L and l-tyrosine residual quantity are 0.05g/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 adjusts pH to 8.Liquid amount is 100ml in 500ml triangular flask, 120 DEG C, is sterilized within 20 minutes, totally 10 bottles.Respectively take
Providencia burhodogranariea ATCC BAA-1590 glycerol tube seed liquor 0.5mL 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 bacterium
Body is centrifuged the thallus of acquisition with twice of sterile water wash.5g wet thallus is taken to be put into the 10ml that l-tyrosine concentration is 0.3g/L molten
In liquid, and pH to 5 is adjusted, is uniformly mixed.After 35 DEG C of shaking tables vibrate (100rpm) 1 hour, filtering with microporous membrane conversion fluid, liquid
D-4- hydroxyphenyl lactic acid concentration is 0.06g/L in analysis of hplc conversion fluid and l-tyrosine residual quantity is 0.05g/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, D-4- hydroxyphenyl lactic acid concentration in liquid-phase chromatographic analysis fermentation liquid
For 0.003g/L.
Claims (4)
1. a kind of method of conversion l-tyrosine production R- (+) -3- (4- hydroxy phenyl) -2 hydroxy propanoic acid, which is characterized in that institute
The method of stating is to carry out conversion production using Providence bacterium microorganism；The Providence bacterium microorganism has: producing 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 l-tyrosine 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, l-tyrosine side can be directly added into thallus incubation
Long thallus side conversion production R- (+) -3- (4- hydroxy phenyl) -2 hydroxy propanoic acid.
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| CN107805620B (en) * | 2017-10-12 | 2021-03-02 | 昆明理工大学 | Genetically engineered bacterium lactococcus lactis and application thereof |
| CN111088197B (en) * | 2020-01-20 | 2021-07-23 | 华南农业大学 | Provevelis alcaligenes and application thereof in degrading tetracycline and producing auxin |
| CN113234768A (en) * | 2021-05-10 | 2021-08-10 | 永州恒飞生物医药有限公司 | Application of providencia in production of hydroxyethyl piperazine ethanesulfonic acid |
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| 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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