CN105603010B - A kind of method of microorganism conversion - Google Patents
A kind of method of microorganism conversion Download PDFInfo
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- CN105603010B CN105603010B CN201610086461.4A CN201610086461A CN105603010B CN 105603010 B CN105603010 B CN 105603010B CN 201610086461 A CN201610086461 A CN 201610086461A CN 105603010 B CN105603010 B CN 105603010B
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Abstract
The present invention relates to produce R- (+) -3- (4- hydroxy phenyl) -2 hydroxy propanoic acid using Morganella microorganism conversion l-tyrosine.This method process is simple, has important industrial application value.
Description
Technical field
The present invention belongs to industrial microorganism field using the root fungus conversion l-tyrosine production D-4- hydroxyphenyl lactic acid that rubs.
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).Have also document show common variation
L-tyrosine can be converted to D-4- hydroxyphenyl lactic acid (The influence of by bacillus (Proteus vulgaris)
conditions of bacterial cleavage of proteins on the cleavage products,1917,
J.Biol.Chem.527-532)。
Based on the significant application value of 4- hydroxyphenyl lactic acid, this patent is proposed using Morganella microorganism conversion L- junket
The scheme of propylhomoserin production D-4- hydroxyphenyl lactic acid.
The root fungus (Morganella) that rubs is a kind of gramnegative bacterium that can make phenylalanine oxidative deamination.Existing 2
Kind and 2 subspecies: Mo Genmo root fungus (Morganella morganii), the cold-resistant root fungus (Morganella that rubs
Psychrotolerans), Mo Genmo root fungus rubs root subspecies (Morganella morganii subsp.morganii) and the root that rubs
Root fungus Xi Baini subspecies of rubbing (Morganella morganii subsp.Sibonii subsp.).The root fungus that rubs has powerful oxygen
Change deamination ability (Sherris Medical Microbiology, 2004,4th ed.), l-tyrosine can be rubbed root fungus oxygen
Change deamination into 4- hydroxyphenyl pyruvate, is then then reduced into D-4- hydroxyphenyl lactic acid.Although 4- hydroxyphenyl pyruvate is more straight
The substrate connect, but it is expensive and unstable, therefore l-tyrosine is optimal substrate.The root fungus that rubs is a kind of facultative anaerobic bacteria,
Production D-4- hydroxyphenyl lactic acid can be converted under anaerobic condition or aerobic condition, have the characteristics that high conversion and high-purity.
Summary of the invention
The present invention produces D-4- hydroxyphenyl lactic acid, technology by culture Morganella microbial cells, conversion l-tyrosine
Scheme is as follows:
1, bacterial strain
Bacterial strain used in the present invention has the Morganella morganii purchased from U.S.'s ATCC strain library
Subsp.sibonii ATCC 49948, Morganella morganii subsp.morganii ATCC 25830 and purchase
From the Morganella morganii CICC 21517 of Chinese industrial Microbiological Culture Collection administrative center and purchased from BCCM/
The Morganella psychrotolerans LMG 23374 of LMG Bacteria Collection.
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, simultaneously constant volume is dissolved in methanol
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 21517 glycerol tube seed liquor of Morganella morganii CICC
1mL inoculation, 30 DEG C of fermentation temperature, shaking speed 200rpm.After culture 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.20g wet thallus is taken to be put into L- junket
Propylhomoserin 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, the supernatant after being converted again
Liquid.Liquid phase analysis D-4- hydroxyphenyl lactic acid concentration is 0.08g/L, and remaining l-tyrosine concentration is 0.12g/L.Using preparation chromatography
Obtain 0.58g sterling.
Polarimeter analyzes its optical activityNuclear magnetic data are as follows: 1H NMR (acetone-d6, D2O,
600MHz): δ 7.05 (1H, d, J=8.0Hz), 7.04 (1H, d, J=8.0Hz), 6.65 (1H, d, J=8.0), 6.64 (2H, d,
J=8.0Hz), 4.23 (2H, dd, J=4.0,8.0Hz), 2.95 (2H, dd, J=4.0,8.0Hz), 2.73 (1H, dd, J=
8.0Hz)；13C N4MR(acetone-d6,D2O, 600MHz): δ 173.02,155.86,130.43,128.29,130.40,
114.86,114.86,71.54,39.6.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.
49948 glycerol tube seed liquor 1mL of Morganella morganii subsp.sibonii ATCC is taken to be inoculated with 1 bottle,
It is cultivated 72 hours for 35 DEG C in anaerobic culture box, is centrifuged the thallus of acquisition with twice of sterile water wash.0.1g wet thallus is taken to be put into
L-tyrosine concentration is 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 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 0.03g/L, and remaining l-tyrosine concentration is 0.02g/L.
49948 glycerol tube seed liquor 1mL of Morganella morganii subsp.sibonii ATCC is taken to be inoculated with 1 bottle,
It is cultivated 24 hours for 35 DEG C in shaking table (200rpm).Fermentation liquid is centrifuged (revolving speed 10000rpm, time 10min), removes supernatant
Liquid obtains thallus, is centrifuged the thallus of acquisition with twice of sterile water wash.It takes 0.1g wet thallus to be put into l-tyrosine concentration to be
In the 4ml solution of 0.02g/L, it is uniformly mixed.After 35 DEG C of shaking tables oscillation (100rpm) 12 hours, 100 DEG C heating water bath 3 minutes
Kill thallus.It is centrifuged (revolving speed 10000rpm, time 10min) removal thallus, the supernatant after being converted again.Liquid phase analysis D-
4- hydroxyphenyl lactic acid concentration is 0.06g/L, and remaining l-tyrosine concentration is 0.08g/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
49948 glycerol tube seed liquor 0.5mL of Morganella morganii subsp.sibonii ATCC inoculation, fermentation temperature 35
DEG C, shaking speed 200rpm.After culture 24, fermentation liquid is centrifuged (revolving speed 10000rpm, time 10min), removal supernatant obtains
Thallus is obtained, is centrifuged the thallus of acquisition with twice of sterile water wash.Taking 0.05g wet thallus to be put into l-tyrosine concentration is 0.01g/L
2ml solution in, and adjust pH to 6, be uniformly mixed.Static conversion 24 hours in anaerobic culture box, filtering with microporous membrane turns
Change liquid, D-4- hydroxyphenyl lactic acid concentration is 0.003g/L in liquid-phase chromatographic analysis conversion fluid and l-tyrosine residual quantity is
0.004g/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
Ferrous 0.5g/L.Liquid amount is 50ml in 250ml triangular flask, 120 DEG C, is sterilized within 20 minutes.Take Morganella morganii
25830 glycerol tube seed liquor 0.5mL of subsp.morganii ATCC inoculation, 20 DEG C of fermentation temperature, shaking speed 200rpm.Training
After supporting 72, 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 0.01g wet thallus to be put into the 2ml solution that l-tyrosine concentration is 0.2g/L, is uniformly mixed.In
20 DEG C of shaking table oscillations (100rpm) are after 24 hours, 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 0.06g/L.
Embodiment 5
Culture medium composition are as follows: xylose 50g/L, ammonium sulfate 1g/L, diammonium hydrogen phosphate 1g/L, potassium dihydrogen phosphate 1g/L, sulfuric acid
Magnesium 0.2g/L.Liquid amount is 50ml in 250ml triangular flask, 120 DEG C, is sterilized within 20 minutes.Take Morganella morganii
25830 glycerol tube seed liquor 0.5mL of subsp.morganii ATCC inoculation, 40 DEG C of fermentation temperature, shaking speed 200rpm.Training
After supporting 48, 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 l-tyrosine concentration is 0.2g/L, is uniformly mixed.In
40 DEG C of shaking table oscillations (100rpm) are after 24 hours, 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 0.09g/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
23374 glycerol tube seed liquor 0.5mL of Morganella psychrotolerans LMG inoculation, 30 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,
It is uniformly mixed.Static conversion 24 hours in 20 DEG C of anaerobic culture boxes, filtering with microporous membrane conversion fluid, liquid-phase chromatographic analysis conversion
D-4- hydroxyphenyl lactic acid concentration is 0.06g/L in liquid and l-tyrosine residual quantity is 0.03g/L.
Embodiment 7
Culture medium composition are as follows: maltose 15g/L, ammonium chloride 1g/L, potassium dihydrogen phosphate 0.1g/L, magnesium sulfate 0.1g/L, sulphur
Sour ferrous iron 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
23374 glycerol tube seed liquor 0.5mL of Morganella psychrotolerans LMG inoculation, 10 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 0.3g/L,
It is uniformly mixed.Static conversion 24 hours in 40 DEG C of anaerobic culture boxes, filtering with microporous membrane conversion fluid, liquid-phase chromatographic analysis conversion
D-4- hydroxyphenyl lactic acid concentration is 0.08g/L in liquid and l-tyrosine residual quantity is 0.16g/L.
Embodiment 8
Culture medium composition are as follows: galactolipin 1g/L, urea 1g/L, diammonium hydrogen phosphate 1g/L, magnesium sulfate 0.1g/L, ferrous sulfate
0.1g/L adjusts pH to 2.Liquid amount is 50ml in 250ml triangular flask, 120 DEG C, is sterilized within 20 minutes.Take Morganella
21517 glycerol tube seed liquor 0.5mL of morganii CICC inoculation, 35 DEG C of fermentation temperature, shaking speed 200rpm.Culture 24
Afterwards, fermentation liquid is centrifuged (revolving speed 10000rpm, time 10min), removal supernatant obtains thallus, is centrifuged the thallus nothing of acquisition
Bacterium water cleans twice.It takes 0.1g wet thallus to be put into the 2ml solution that l-tyrosine concentration is 0.2g/L, and adjusts pH to 2, mix
Uniformly.Static conversion 24 hours, filtering with microporous membrane conversion fluid, in liquid-phase chromatographic analysis conversion fluid in 37 DEG C of anaerobic culture boxes
D-4- hydroxyphenyl lactic acid concentration is 0.01g/L and l-tyrosine residual quantity is 0.15g/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, l-tyrosine 0.2g/L adjust pH to 8.Liquid amount is 50ml in 250ml triangular flask,
It 120 DEG C, sterilizes within 20 minutes.21517 glycerol tube seed liquor 0.5mL of Morganella morganii CICC is taken to be inoculated with, fermentation temperature
35 DEG C of degree, shaking speed 200rpm.After culture 24, filtering with microporous membrane conversion fluid, D-4- hydroxyl in liquid-phase chromatographic analysis conversion fluid
Base phenyllactic acid concentration is 0.03g/L and l-tyrosine residual quantity is 0.02g/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.Morganella morganii CICC21517 glycerol tube seed liquor 0.5mL is respectively taken to be inoculated with, fermentation temperature 35
DEG C, shaking speed 200rpm.After culture 24, fermentation liquid is centrifuged (revolving speed 10000rpm, time 10min), removal supernatant obtains
Thallus is obtained, is centrifuged the thallus of acquisition with twice of sterile water wash.Taking 5g wet thallus to be put into l-tyrosine concentration is 0.3g/L's
In 10ml solution, and pH to 5 is adjusted, is uniformly mixed.After 35 DEG C of shaking tables vibrate (100rpm) 1 hour, filtering with microporous membrane turns
Change liquid, D-4- hydroxyphenyl lactic acid concentration is 0.12g/L in liquid-phase chromatographic analysis conversion fluid and l-tyrosine residual quantity is 0.06g/
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.
49948 glycerol tube seed liquor 0.5mL of Morganella morganii subsp.sibonii ATCC is taken to be inoculated with, fermentation temperature
35 DEG C, shaking speed 200rpm.After culture 24, filtering with microporous membrane conversion fluid, D-4- hydroxyl in liquid-phase chromatographic analysis conversion fluid
Phenyllactic acid concentration is 0.001g/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 Morganella microorganism；The Morganella microorganism is respectively for deposit number
The bacterial strain of CICC21517, ATCC 49948, ATCC 25830, LMG 23374；
The step of conversion process uses is as follows:
(1) l-tyrosine substrate is added in cultivating system the liquid incubation of cell；L-tyrosine additive amount is 0-
0.3g/L；
(2) liquid state fermentation culture is centrifuged removal fermentation liquid and obtains thallus, thallus is put into the water containing l-tyrosine substrate
It is carried out in solution reaction system；Conversion process temperature is 20-40 DEG C, pH 2-8, and transformation time is 1-24 hours；In conversion fluid
L-tyrosine initial concentration is 0.1-0.3g/L.
2. the method according to claim 1, wherein the incubation of the Morganella microorganism can detest
Oxygen condition can also be carried out in aerobic 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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