CN105603008B - A kind of method of microorganism conversion - Google Patents
A kind of method of microorganism conversion Download PDFInfo
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Abstract
The present invention relates to produce R- (-)-indoles -3- lactic acid using Providence bacterium microorganism conversion L-Trp.This method process is simple, has important industrial application value.
Description
Technical field
The present invention produces R- (-)-indoles -3- lactic acid using Providence bacterium conversion L-Trp, belongs to the micro- life of industry
Object field.
Background technique
R- (-)-indoles -3- lactic acid is also R- (-) -3- indole-lactate, English name are as follows: R- (-)-indole-3-lactic
acid、R-(-)-2-hydroxy-3-(1H-indol-3-yl)propanoic acid、R-(-)-Indolelactic acid、
R-(-)-Indolelactate.It has antibacterial activity, while being also the precursor of plant hormone heteroauxin.Based on R- (-)-
The significant application value of indoles -3- lactic acid, this patent, which is proposed, produces R- using Proteus microorganism conversion L-Trp
The scheme of (-)-indoles -3- lactic acid.Currently mainly by Production by Microorganism Fermentation, abundant raw material is easy to get L-Trp.
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.),
L-Trp can be by Providence bacterium oxidative deamination at indole-3-pyruvic acid.
Pertinent literature thinks that L-Trp can only be oxidized to indole-3-pyruvic acid by these microorganisms, and can not be further
Be reduced into indoles -3- lactic acid (α-keto acids are novel siderophores in the genera proteus,
Providencia, and morganella and are produced by amino acid deaminases, 1993,
Journal of bacteriology, 175 (9), 2727-2733), this may therewith condition selection it is improper related.
L-Trp can be converted to optically pure R- (-)-indoles -3- by Providence bacterium microorganism by the present invention
Lactic acid.Although indole-3-pyruvic acid is more direct substrate, but price is higher, therefore L-Trp is optimal substrate.It is general
Luo Weidengsi bacterium is a kind of facultative anaerobic bacteria, and production R- (-)-indoles -3- cream can be converted under anaerobic condition or aerobic condition
Acid has the characteristics that high conversion and high-purity.
Summary of the invention
The present invention produces R- (-)-indoles -3- by culture Providence bacterium microorganism thallus, conversion L-Trp
Lactic acid, technical solution are as follows:
1, bacterial strain
Bacterial strain used in the present invention has the Providencia alcalifaciensATCC 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 R- (-)-indoles -3- lactic acid
The scheme that conversion process uses has 2 kinds:
(1) the liquid incubation of cell, L-Trp substrate is added in above-mentioned cultivating system；L-Trp addition
Amount is 0-10g/L.
(2) liquid state fermentation culture is centrifuged removal fermentation liquid and obtains thallus, thallus is put into containing L-Trp 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
Tryptophan initial concentration is 0.1-10g/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 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 100 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.40g wet thallus is taken to be put into L-
Tryptophan concentration is to be uniformly mixed in the 1000ml solution of 10g/L.After 37 DEG C of shaking tables vibrate (100rpm) 48 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 R- (-)-indoles -3- lactic acid concn is 2.2g/L, and remaining L-Trp concentration is 3.1g/L.Using preparing color
Spectrum obtains 1.9g sterling.
Polarimeter analyzes its optical activityNuclear magnetic data are as follows: 1H NMR (D2O 600MHz):δ
7.76 (1H, d J 7.9Hz), 7.42 (1H, d, J 8.1Hz), 7.23 (2H, m, J 7.6Hz), 7.15 (1H, d, J 0.98,
7.49Hz), 4.36 (1H, dd, J 4.29,7.65), 3.25 (1H, ddd, J 4.26,4.85Hz), 3.12 (1H, dd, J 7.65,
14.86Hz)。13C NMR(D2O, 600MHz): δ 183.67,138.72,129.83,126.87,124.45,121.63,
121.46,114.25,113.61,74.42,32.67.
The mass spectrometric data of converted product are as follows: (- ESI, negative mode) m/z:204.0 [M-1].
According to above data, determine that its molecule and optical texture and R- (-)-indoles -3- 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-Trp 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
R- (-)-indoles -3- lactic acid concn is 0.2g/L, and remaining L-Trp concentration is 0.6g/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-Trp 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 R- (-)-indoles -3- cream
Acid concentration is 0.5g/L, and remaining L-Trp concentration is 0.4g/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-Trp 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 R- (-)-indoles -3- lactic acid concn in conversion fluid is 0.005g/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.0.1g wet thallus is taken to be put into the 2ml solution that L-Trp concentration is 2g/L, mixing
Uniformly.After 20 DEG C of shaking tables oscillation (100rpm) 24 hours, filtering with microporous membrane conversion fluid, R- in liquid-phase chromatographic analysis conversion fluid
(-)-indoles -3- lactic acid concn is 0.3g/L and L-Trp residual quantity is 0.5g/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-Trp 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, R- (-)-indoles -3- lactic acid is dense in liquid-phase chromatographic analysis conversion fluid
Degree is 0.6g/L and L-Trp residual quantity is 0.9g/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-Trp concentration is 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
R- (-)-indoles -3- lactic acid concn is 0.3g/L in liquid and L-Trp residual quantity is 0.8g/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-Trp concentration is 3g/L, is uniformly mixed.In 40 DEG C
Static conversion 24 hours, filtering with microporous membrane conversion fluid, R- (-)-indoles-in liquid-phase chromatographic analysis conversion fluid in anaerobic culture box
3- lactic acid concn is 0.8g/L and L-Trp residual quantity is 0.9g/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-Trp 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
R- (-)-indoles -3- lactic acid concn is 0.2g/L in spectrum analysis conversion fluid and L-Trp residual quantity is 0.8g/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-Trp 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, R- (-)-indoles -3- lactic acid is dense in liquid-phase chromatographic analysis conversion fluid
Degree is 0.2g/L and L-Trp residual quantity is 0.4g/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 solution that L-Trp concentration is 10g/L
In, and pH to 5 is adjusted, it is uniformly mixed.After 35 DEG C of shaking tables vibrate (100rpm) 10 hours, filtering with microporous membrane conversion fluid, liquid
R- (-)-indoles -3- lactic acid concn is 3.4g/L in analysis of hplc conversion fluid and L-Trp residual quantity is 2.6g/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, R- (-)-indoles -3- lactic acid in liquid-phase chromatographic analysis fermentation liquid
Concentration is 0.006g/L.
Claims (4)
1. a kind of method of conversion L-Trp production R- (-)-indoles -3- lactic acid, which is characterized in that the method is using general
Luo Weidengsi bacterium microorganism carries out conversion production；The Providence bacterium microorganism has: produce alkali Providence, this
Family name's Providence, 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-Trp 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-Trp side can be directly added into thallus incubation
Long thallus side conversion production R- (-)-indoles -3- lactic acid.
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| Publication number | Priority date | Publication date | Assignee | Title |
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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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- 2016-02-15 CN CN201610085603.5A patent/CN105603008B/en active Active
Patent Citations (4)
| 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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