CN105624228B - A kind of method of microorganism conversion - Google Patents
A kind of method of microorganism conversion Download PDFInfo
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- CN105624228B CN105624228B CN201610085340.8A CN201610085340A CN105624228B CN 105624228 B CN105624228 B CN 105624228B CN 201610085340 A CN201610085340 A CN 201610085340A CN 105624228 B CN105624228 B CN 105624228B
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Abstract
The present invention relates to produce R- (-)-indoles -3- lactic acid using Proteus 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 proteus conversion L-Trp, belongs to industrial microorganism neck
Domain.
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.
Proteus (Proteus) be it is widely distributed in nature, such as soil, water, rubbish, spoilage organism and people or
Microorganism in the enteron aisle of animal.Existing 5 kinds: proteus vulgaris (Proteus vulgaris), proteus mirabilis
(Proteus mirabilis), glutinous proteus (Proteus myxofaciens), Pan Shi proteus (Proteus are produced
) and Hao Shi proteus (Proteus hauseri) penneri.Proteus has powerful oxidative deamination ability
(Sherris Medical Microbiology, 2004,4th ed.), L-Trp can by proteus oxidative deamination at
Indole-3-pyruvic acid.
Pertinent literature thinks that L-Trp can only be oxidized to indole-3-pyruvic acid by proteus microorganism belonging to genus, and can not
Further it is 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- cream by proteus microorganism belonging to genus by the present invention
Acid.Although indole-3-pyruvic acid is more direct substrate, but price is higher, therefore L-Trp is optimal substrate.Deformation
Bacillus is a kind of facultative anaerobic bacteria, and production R- (-)-indoles -3- lactic acid can be converted under anaerobic condition or aerobic condition, is had
The characteristics of high conversion and high-purity.
Summary of the invention
The present invention produces R- (-)-indoles -3- lactic acid by culture Proteus microbial cells, conversion L-Trp,
Technical solution is as follows:
1, bacterial strain
Bacterial strain used in the present invention have Proteus mirabilis ATCC 29906 purchased from U.S.'s ATCC strain library,
Proteus myxofaciens ATCC 19692、Proteus hauseri ATCC 700826、Proteus penneri
ATCC 33519、Proteus mirabilis ATCC 25933、Proteus mirabilis ATCC 33946、Proteus
Vulgaris ATCC 19181, Proteus vulgaris ATCC 27972 and be purchased from Chinese industrial Microbiological Culture Collection
Proteus vulgaris CICC 10401, the Proteus mirabilis CICC 22928 of administrative 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 50 bottles, 120 DEG C, sterilize within 20 minutes.Take 29906 glycerol tube seed liquor 1mL of Proteus mirabilis ATCC
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- color
Propylhomoserin 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 of water
Bath 3 minutes killing thallus of heating.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 4.2g/L, and remaining L-Trp concentration is 4.6g/L.Using preparing color
Spectrum obtains 2.9g sterling.
Polarimeter analyzes its optical activityNuclear magnetic data are as follows: 1H NMR (D2O 600MHz):δ
7.75 (1H, d J 7.9Hz), 7.46 (1H, d, J 8.1Hz), 7.21 (2H, m, J 7.6Hz), 7.13 (1H, d, J 0.98,
7.49Hz), 4.32 (1H, dd, J 4.29,7.65), 3.25 (1H, ddd, J 4.26,4.85Hz), 3.14 (1H, dd, J 7.65,
14.86Hz)。13C NMR(D2O, 600MHz): δ 183.86,138.79,129.95,126.95,124.43,121.61,
121.42,114.23,113.51,74.32,32.71.
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.
22928 glycerol tube seed liquor 1mL of Proteus mirabilis CICC is taken to be inoculated with 1 bottle, 35 in anaerobic culture box
DEG C culture 72 hours, be centrifuged the thallus of acquisition with twice of sterile water wash.Taking 0.1g wet thallus to be put into L-Trp concentration is 5g/
It in the 4ml solution of L, is uniformly mixed, after 35 DEG C of standings convert 24 hours in anaerobic culture box, 100 DEG C are killed for heating water bath 3 minutes
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 2.3g/L, and remaining L-Trp concentration is 1.6g/L.
22928 glycerol tube seed liquor 1mL of Proteus mirabilis CICC is taken to be inoculated with 1 bottle, in shaking table (200rpm)
35 DEG C are cultivated 24 hours.Fermentation liquid is centrifuged (revolving speed 10000rpm, time 10min), removal supernatant obtains thallus, and centrifugation obtains
The thallus obtained is with twice of sterile water wash.0.1g wet thallus is taken to be put into the 4ml solution that L-Trp concentration is 5g/L, mixing is equal
It is even.After 35 DEG C of shaking tables vibrate (100rpm) 12 hours, 100 DEG C of heating water baths, 3 minutes killing thallus.It is centrifuged (revolving speed again
10000rpm, time 10min) removal thallus, the supernatant after being converted.Liquid phase analysis R- (-)-indoles -3- lactic acid concn
For 2.1g/L, remaining L-Trp concentration is 1.3g/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.Take Proteus
19181 glycerol tube seed liquor 0.5mL of vulgaris ATCC 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 0.05g wet thallus to be put into the 2ml solution that L-Trp concentration is 0.1g/L, and adjusts pH to 6, mix
It closes uniform.Static conversion 24 hours, filtering with microporous membrane conversion fluid, R- in liquid-phase chromatographic analysis conversion fluid in anaerobic culture box
(-)-indoles -3- lactic acid concn is 0.02g/L and L-Trp residual quantity 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
Ferrous 0.5g/L.Liquid amount is 50ml in 250ml triangular flask, 120 DEG C, is sterilized within 20 minutes.Take Proteus hauseri ATCC
700826 glycerol tube seed liquor 0.5mL inoculation, 20 DEG C of fermentation temperature, shaking speed 200rpm.After culture 72, fermentation liquid is centrifuged
(revolving speed 10000rpm, time 10min), removal supernatant obtain thallus, are centrifuged the thallus of acquisition with twice of sterile water wash.It takes
0.1g wet thallus is put into the 2ml solution that L-Trp concentration is 1g/L, is uniformly mixed.(100rpm) 24 is vibrated in 20 DEG C of shaking tables
After hour, filtering with microporous membrane conversion fluid, in liquid-phase chromatographic analysis conversion fluid R- (-)-indoles -3- lactic acid concn be 0.4g/L and
L-Trp residual quantity is 0.3g/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 Proteus vulgaris CICC
10401 glycerol tube seed liquor 0.5mL inoculation, 40 DEG C of fermentation temperature, shaking speed 200rpm.After culture 48, fermentation liquid is centrifuged
(revolving speed 10000rpm, time 10min), removal supernatant obtain thallus, are centrifuged the thallus of acquisition with twice of sterile water wash.It takes
0.1g wet thallus is put into the 2ml solution that L-Trp concentration is 2g/L, is uniformly mixed.(100rpm) 24 is vibrated in 40 DEG C of shaking tables
After hour, filtering with microporous membrane conversion fluid, in liquid-phase chromatographic analysis conversion fluid R- (-)-indoles -3- lactic acid concn be 0.5g/L and
L-Trp residual quantity is 1.0g/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
19692 glycerol tube seed liquor 0.5mL of Proteus myxofaciens ATCC 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, 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.Static conversion 24 hours, filtering with microporous membrane conversion fluid, in liquid-phase chromatographic analysis conversion fluid in 20 DEG C of anaerobic culture boxes
R- (-)-indoles -3- lactic acid concn is 0.4g/L and L-Trp residual quantity is 1.3g/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, ferrous sulfate 0.1g/L adjust pH to 5.In 250ml triangular flask liquid amount be 50ml, 120 DEG C, 20 minutes
Sterilizing.27972 glycerol tube seed liquor 0.5mL of Proteus vulgaris ATCC is taken to be inoculated with, 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.0.1g wet thallus is taken to be put into the 2ml solution that L-Trp concentration is 3g/L, mixing
Uniformly.Static conversion 24 hours, filtering with microporous membrane conversion fluid, in liquid-phase chromatographic analysis conversion fluid in 40 DEG C of anaerobic culture boxes
R- (-)-indoles -3- lactic acid concn is 1.5g/L and L-Trp residual quantity is 1.0g/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.
25933 glycerol tube seed liquor 0.5mL of Proteus vulgaris ATCC is taken to be inoculated with, 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.It takes 0.1g wet thallus to be put into the 2ml solution that L-Trp concentration is 2g/L, and adjusts
PH to 2 is saved, is uniformly mixed.Static conversion 24 hours, filtering with microporous membrane conversion fluid, liquid chromatogram in 37 DEG C of anaerobic culture boxes
R- (-)-indoles -3- lactic acid concn is 0.3g/L in analysis conversion fluid and L-Trp residual quantity is 1.3g/L.
Embodiment 9
Culture medium composition are as follows: glucose 1g/L, peptone 1g/L, potassium dihydrogen phosphate 0.1g/L, magnesium sulfate 0.1g/L, sulfuric acid
Ferrous 0.1g/L, L-Trp 2g/L adjust pH to 8.Liquid amount is 50ml in 250ml triangular flask, 120 DEG C, is sterilized within 20 minutes.
33946 glycerol tube seed liquor 0.5mL of Proteus mirabilis ATCC is taken to be inoculated with, 35 DEG C of fermentation temperature, shaking speed
200rpm.After culture 24, filtering with microporous membrane conversion fluid, R- (-)-indoles -3- lactic acid concn in liquid-phase chromatographic analysis conversion fluid
It is 0.2g/L for 0.8g/L and L-Trp residual quantity.
Embodiment 10
Culture medium composition are as follows: glucose 1g/L, urea 1g/L, diammonium hydrogen phosphate 1g/L, magnesium sulfate 0.1g/L, ferrous sulfate
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
33519 glycerol tube seed liquor 0.5mL of Proteus penneri ATCC 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, is centrifuged the bacterium of acquisition
Body is with twice of sterile water wash.It takes 5g wet thallus to be put into the 10ml solution that L-Trp concentration is 3g/L, and adjusts pH to 5,
It is uniformly mixed.After 35 DEG C of shaking tables vibrate (100rpm) 1 hour, filtering with microporous membrane conversion fluid, liquid-phase chromatographic analysis conversion fluid
Middle R- (-)-indoles -3- lactic acid concn is 2.2g/L and L-Trp residual quantity is 0.3g/L.
Embodiment 11
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.Adjust pH to 5.Liquid amount is 50ml in 250ml triangular flask, 120 DEG C, is gone out within 20 minutes
Bacterium.33946 glycerol tube seed liquor 0.5mL of Proteus mirabilis ATCC is taken to be inoculated with, 37 DEG C of fermentation temperature, shaking speed
200rpm.After culture 24, filtering with microporous membrane conversion fluid, R- (-)-indoles -3- lactic acid concn in liquid-phase chromatographic analysis fermentation liquid
For 0.1g/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 to utilize change
Shape bacillus spp. microorganism carries out conversion production；The proteus microorganism belonging to genus has: proteus vulgaris, proteus mirabilis,
Produce glutinous proteus, Pan Shi proteus and Hao Shi proteus.
2. the method according to claim 1, wherein the incubation of the proteus microorganism belonging to genus can be
Anaerobic state 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-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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| CN103045514A (en) * | 2012-12-27 | 2013-04-17 | 江南大学 | Proteus mirabilis for synthetizing acidic ethyl urethane hydrolytic enzyme and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102925535A (en) * | 2012-11-26 | 2013-02-13 | 厦门大学 | Screening and identification method of electricigen enzyme |
| CN103045514A (en) * | 2012-12-27 | 2013-04-17 | 江南大学 | Proteus mirabilis for synthetizing acidic ethyl urethane hydrolytic enzyme and application thereof |
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| Title |
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| A comparison of the phenylpyruvic acid reaction and the urease test in the differentiation of Proteus from other enteric organisms;Henriksen S D等;《 Journal of Bacteriology》;19501231;第60卷(第3期);全文 |
| Production and degradation of indole by gram-negative bacteria;HE Müller等;《 Zentralblatt Für Bakteriologie Mikrobiologie Und Hygiene》;19861231;第261卷(第1期);全文 |
| Regulation of Phenylalanine Oxidase Synthesis in Proteus;ANNE-MARIE等;《JOURNAL OF BACTERIOLOGY》;19790131;第137卷(第1期);第161页摘要 |
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