CN105543305A - Microbial transformation method - Google Patents
Microbial transformation method Download PDFInfo
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- CN105543305A CN105543305A CN201610085564.9A CN201610085564A CN105543305A CN 105543305 A CN105543305 A CN 105543305A CN 201610085564 A CN201610085564 A CN 201610085564A CN 105543305 A CN105543305 A CN 105543305A
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Abstract
The invention relates to a method for producing R-(-)-indole-3-lactic acid by transforming L-tryptophan by adopting morganella microbes. The method is simple in process and has important industrial application value.
Description
Technical field
The present invention adopts the root fungus that rubs to transform L-Trp and produces R-(-)-indoles-3-lactic acid, belongs to industrial microorganism field.
Background technology
R-(-)-indoles-3-lactic acid is also R-(-)-3-indole-lactate, English by name: R-(-)-indole-3-lacticacid, R-(-)-2-hydroxy-3-(1H-indol-3-yl) propanoicacid, R-(-)-Indolelacticacid, R-(-)-Indolelactate.It has anti-microbial activity, is also the precursor of plant hormone indolylacetic acid simultaneously.Based on the significant application value of R-(-)-indoles-3-lactic acid, this patent proposes the scheme adopting proteus microbial transformation L-Trp to produce R-(-)-indoles-3-lactic acid.L-Trp is current mainly through Production by Microorganism Fermentation, and abundant raw material is easy to get.
The root fungus (Morganella) that rubs is the gram negative bacterium that a class can make phenylalanine oxidative deamination.Existing 2 kinds and 2 subspecies: Mo Genmo root fungus (Morganellamorganii), the cold-resistant root fungus that rubs (Morganellapsychrotolerans), Mo Genmo root fungus rub root subspecies (Morganellamorganiisubsp.morganii) and Mo Genmo root fungus Xi Baini subspecies (Morganellamorganiisubsp.Siboniisubsp.).The root fungus that rubs has powerful oxidative deamination ability (SherrisMedicalMicrobiology, 2004,4thed.), and the L-Trp root fungus oxidative deamination that can be rubbed becomes indole-3-pyruvic acid.
Pertinent literature thinks that L-Trp can only be oxidized to indole-3-pyruvic acid by these microorganisms, and indoles-3-lactic acid (α-ketoacidsarenovelsiderophoresinthegeneraproteus cannot be reduced into further, providencia, andmorganellaandareproducedbyaminoaciddeaminases, 1993, Journalofbacteriology, 175 (9), 2727-2733), this may condition select improper relevant with it.
L-Trp is changed into optically pure R-(-)-indoles-3-lactic acid by Morganella microorganism by the present invention.Although indole-3-pyruvic acid is more direct substrate, price is higher, and therefore L-Trp is best substrate.The root fungus that rubs is a kind of facultative anaerobe, can transform and produce R-(-)-indoles-3-lactic acid, have high conversion and highly purified feature under anaerobic condition or aerobic condition.
Summary of the invention
The present invention is by cultivating Morganella microbial cells, and transform L-Trp and produce R-(-)-indoles-3-lactic acid, technical scheme is as follows:
1, bacterial strain
The present invention's bacterial strain used have purchased from American ATCC strain library Morganellamorganiisubsp.siboniiATCC49948, Morganellamorganiisubsp.morganiiATCC25830 and purchased from the MorganellamorganiiCICC21517 of Chinese industrial Microbiological Culture Collection administrative center and the MorganellapsychrotoleransLMG23374 purchased from BCCM/LMGBacteriaCollection.
2, yeast culture
Liquid state fermentation substratum consists of: carbon source 0-50g/L, nitrogenous source 0-50g/L, Secondary ammonium phosphate 0-2g/L, potassium primary phosphate 0-1g/L, magnesium sulfate 0-0.5g/L, ferrous sulfate 0-0.5g/L, sodium chloride 0-5g/L, adjustable pH to 2-8, can also pH nature; Inoculum size is 5-20%, and leavening temperature is 20-40 DEG C, and fermentation period is 24-72 hour.Seed and fermentation all adopt this substratum.
Can be glucose, fructose, maltose, wood sugar, sucrose, semi-lactosi, glycerine for cultivating the carbon source of bacterial classification.Cultivation nitrogenous source can be the organic nitrogen sources such as ammonium sulfate, ammonium chloride, ammonium nitrate, peptone, yeast extract paste, urea, corn steep liquor.Carbon and nitrogen sources can be one or more combination.
Liquid process of cultivating thalline can adopt anaerobism or aerobic mode.
3, product R-(-)-indoles-3-lactic acid is transformed
The scheme that conversion process adopts has 2 kinds:
(1) the liquid culturing process of cell, adds L-Trp substrate in above-mentioned culture system; L-Trp addition is 0-10g/L.
(2) liquid state fermentation culture centrifugal segregation fermented liquid is obtained thalline, the reactant aqueous solution system put into by thalline containing L-Trp substrate is carried out; Conversion process temperature 20-40 DEG C, pH2-8, transformation time 1-24 hour.In conversion fluid, L-Trp initial concentration is 0.1-10g/L.
4, the detection analysis of sample
Conversion fluid adopts PerkinElmerSeries200 high performance liquid chromatograph to detect and analyzes, chromatographic condition is: moving phase is methyl alcohol-0.1% formic acid water (40:60), adopts Chinese nation MegresC18 chromatographic column (4.6 × 250mm, 5 μm), flow velocity 0.6ml/min, column temperature 30 DEG C, sample size 20 μ l, detector wavelength 200nm.
Adopt the DAC-HB50 preparative chromatography Column preparation of Hanbon Sci. & Tech. Co., Ltd. to transform sample, preparative chromatography condition is: moving phase 50% methyl alcohol, column temperature nature, flow velocity 3ml/min, sample size 5ml.Sample reaches chromatographically pure 99.9%, and sample introduction is separated the product vacuum rotating evaporate to dryness at 50 DEG C obtained repeatedly.Take the sample 0.5g prepared, to be dissolved in deionized water and to be settled to 50ml, adopt Japan's full-automatic polarimeter of AP-300 of liking to delay to measure degree of giving out light.Adopt the nuclear magnetic data of VarianGemini2000 (VnmrS600MHz, 600/54/ASP) analytic sample further.Sample adopts UPLC-QTOF-MS method analyzing molecules amount further, and instrument is WatersMALDISYNAPTQTOFMS liquid chromatography tandem quadrupole time-of-flight mass spectrometer.
Embodiment
Embodiment 1
The analysis of converted product measures.
Preparation substratum is as follows: yeast extract paste 5g/L, peptone 10g/L, sodium-chlor 5g/L.In 500ml triangular flask, liquid amount is 100ml, totally 50 bottles, 120 DEG C, sterilizing in 20 minutes.Get MorganellamorganiiCICC21517 glycerine pipe seed liquor 1mL to inoculate, leavening temperature 30 DEG C, shaking speed 200rpm.After cultivating 24, by centrifugal for fermented liquid (rotating speed 10000rpm, time 10min), remove supernatant liquor and obtain thalline, the thalline sterile water wash of centrifugal acquisition twice.Get 20g wet thallus and put into the 1000ml solution that L-Trp concentration is 10g/L, mix.In 37 DEG C of shaking tables vibration (100rpm) after 24 hours, 100 DEG C of heating in water bath kill thalline in 3 minutes.Centrifugal (rotating speed 10000rpm, time 10min) removes thalline again, obtains the supernatant liquor after transforming.Liquid phase analysis R-(-)-indoles-3-lactic acid concn is 2.2g/L, and residue L-Trp concentration is 5.1g/L.Preparative chromatography is adopted to obtain 1.8g sterling.
Its specific rotation analyzed by polarimeter
nuclear magnetic data is: 1HNMR (D
2o600MHz): δ 7.75 (1H, dJ7.9Hz), 7.45 (1H, d, J8.1Hz), 7.23 (2H, m, J7.6Hz), 7.14 (1H, d, J0.98,7.49Hz), 4.35 (1H, dd, J4.29,7.65), 3.22 (1H, ddd, J4.26,4.85Hz), 3.11 (1H, dd, J7.65,14.86Hz).13CNMR(D
2O,600MHz):δ183.73，138.43，129.62，
126.45，124.23，121.52，121.34，114.12，113.46，74.42，32.32。
The mass-spectrometric data of converted product is: (-ESI, negativemode) 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 cultivation with detest comparing of cultivation.Preparation substratum: glucose 30g/L, peptone 20g/L, Secondary ammonium phosphate 1g/L, potassium primary phosphate 1g/L, magnesium sulfate 0.3g/L, ferrous sulfate 0.3g/L; It is 100ml that initial pH and fermenting process pH is liquid amount in nature 500ml triangular flask, totally 2 bottles, 120 DEG C, sterilizing in 20 minutes.
Get Morganellamorganiisubsp.siboniiATCC49948 glycerine pipe seed liquor 1mL and inoculate 1 bottle, cultivate 72 hours for 35 DEG C in anaerobic culture box, the thalline sterile water wash of centrifugal acquisition twice.Get 0.1g wet thallus and put into the 4ml solution that L-Trp concentration is 2g/L, mix, in anaerobic culture box, 35 DEG C of standing conversions are after 24 hours, and 100 DEG C of heating in water bath kill thalline in 3 minutes.Centrifugal (rotating speed 10000rpm, time 10min) removes thalline again, obtains the supernatant liquor after transforming.Liquid phase analysis R-(-)-indoles-3-lactic acid concn is 0.6g/L, and residue L-Trp concentration is 0.5g/L.
Get Morganellamorganiisubsp.siboniiATCC49948 glycerine pipe seed liquor 1mL and inoculate 1 bottle, cultivate 24 hours for 35 DEG C in shaking table (200rpm).By centrifugal for fermented liquid (rotating speed 10000rpm, time 10min), remove supernatant liquor and obtain thalline, the thalline sterile water wash of centrifugal acquisition twice.Get 0.1g wet thallus and put into the 4ml solution that L-Trp concentration is 2g/L, mix.In 35 DEG C of shaking tables vibration (100rpm) after 12 hours, 100 DEG C of heating in water bath kill thalline in 3 minutes.Centrifugal (rotating speed 10000rpm, time 10min) removes thalline again, obtains the supernatant liquor after transforming.Liquid phase analysis R-(-)-indoles-3-lactic acid concn is 0.5g/L, and residue L-Trp concentration is 0.5g/L.
Embodiment 3
Substratum consists of: glucose 1g/L, urea 1g/L, Secondary ammonium phosphate 1g/L, potassium primary phosphate 0.1g/L, magnesium sulfate 0.1g/L, ferrous sulfate 0.1g/L.In 250ml triangular flask, liquid amount is 50ml, 120 DEG C, sterilizing in 20 minutes.Get Morganellamorganiisubsp.siboniiATCC49948 glycerine pipe seed liquor 0.5mL to inoculate, leavening temperature 35 DEG C, shaking speed 200rpm.After cultivating 24, by centrifugal for fermented liquid (rotating speed 10000rpm, time 10min), remove supernatant liquor and obtain thalline, the thalline sterile water wash of centrifugal acquisition twice.Get 0.05g wet thallus and put into the 2ml solution that L-Trp concentration is 0.1g/L, and regulate pH to 6, mix.Static conversion 24 hours in anaerobic culture box, filtering with microporous membrane conversion fluid, in liquid-phase chromatographic analysis conversion fluid, R-(-)-indoles-3-lactic acid concn is 0.01g/L and L-Trp residual quantity is 0.02g/L.
Embodiment 4
Substratum consists of: fructose 50g/L, ammonium sulfate 5g/L, potassium primary phosphate 1g/L, magnesium sulfate 0.5g/L, ferrous sulfate 0.5g/L.In 250ml triangular flask, liquid amount is 50ml, 120 DEG C, sterilizing in 20 minutes.Get Morganellamorganiisubsp.morganiiATCC25830 glycerine pipe seed liquor 0.5mL to inoculate, leavening temperature 20 DEG C, shaking speed 200rpm.After cultivating 72, by centrifugal for fermented liquid (rotating speed 10000rpm, time 10min), remove supernatant liquor and obtain thalline, the thalline sterile water wash of centrifugal acquisition twice.Get 0.1g wet thallus and put into the 2ml solution that L-Trp concentration is 2g/L, mix.In 20 DEG C of shaking tables vibration (100rpm) after 24 hours, filtering with microporous membrane conversion fluid, in liquid-phase chromatographic analysis conversion fluid, R-(-)-indoles-3-lactic acid concn is 0.4g/L and L-Trp residual quantity is 0.5g/L.
Embodiment 5
Substratum consists of: wood sugar 50g/L, ammonium sulfate 1g/L, Secondary ammonium phosphate 1g/L, potassium primary phosphate 1g/L, magnesium sulfate 0.2g/L.In 250ml triangular flask, liquid amount is 50ml, 120 DEG C, sterilizing in 20 minutes.Get Morganellamorganiisubsp.morganiiATCC25830 glycerine pipe seed liquor 0.5mL to inoculate, leavening temperature 40 DEG C, shaking speed 200rpm.After cultivating 48, by centrifugal for fermented liquid (rotating speed 10000rpm, time 10min), remove supernatant liquor and obtain thalline, the thalline sterile water wash of centrifugal acquisition twice.Get 0.1g wet thallus and put into the 2ml solution that L-Trp concentration is 2g/L, mix.In 40 DEG C of shaking tables vibration (100rpm) after 24 hours, filtering with microporous membrane conversion fluid, in liquid-phase chromatographic analysis conversion fluid, R-(-)-indoles-3-lactic acid concn is 0.7g/L and L-Trp residual quantity is 1.2g/L.
Embodiment 6
Substratum consists of: glycerine 15g/L, ammonium nitrate 1g/L, Secondary ammonium phosphate 1g/L, potassium primary phosphate 0.1g/L, magnesium sulfate 0.1g/L, ferrous sulfate 0.1g/L.In 250ml triangular flask, liquid amount is 50ml, 120 DEG C, sterilizing in 20 minutes.Get MorganellapsychrotoleransLMG23374 glycerine pipe seed liquor 0.5mL to inoculate, leavening temperature 30 DEG C, shaking speed 200rpm.After cultivating 24, by centrifugal for fermented liquid (rotating speed 10000rpm, time 10min), remove supernatant liquor and obtain thalline, the thalline sterile water wash of centrifugal acquisition twice.Get 0.1g wet thallus and put into the 2ml solution that L-Trp concentration is 2g/L, mix.Static conversion 24 hours in 20 DEG C of anaerobic culture boxes, filtering with microporous membrane conversion fluid, in liquid-phase chromatographic analysis conversion fluid, R-(-)-indoles-3-lactic acid concn is 0.5g/L and L-Trp residual quantity is 0.6g/L.
Embodiment 7
Substratum consists of: maltose 15g/L, ammonium chloride 1g/L, Secondary ammonium phosphate 1g/L, potassium primary phosphate 0.1g/L, magnesium sulfate 0.1g/L, ferrous sulfate 0.1g/L, regulates pH to 5.In 250ml triangular flask, liquid amount is 50ml, totally 10 bottles, 120 DEG C, sterilizing in 20 minutes.Get MorganellapsychrotoleransLMG23374 glycerine pipe seed liquor 0.5mL to inoculate, leavening temperature 10 DEG C, shaking speed 200rpm.After cultivating 24, by centrifugal for fermented liquid (rotating speed 10000rpm, time 10min), remove supernatant liquor and obtain thalline, the thalline sterile water wash of centrifugal acquisition twice.Get 1g wet thallus and put into the 2ml solution that L-Trp concentration is 10g/L, mix.Static conversion 24 hours in 40 DEG C of anaerobic culture boxes, filtering with microporous membrane conversion fluid, in liquid-phase chromatographic analysis conversion fluid, R-(-)-indoles-3-lactic acid concn is 3.2g/L and L-Trp residual quantity is 2.4g/L.
Embodiment 8
Substratum consists of: semi-lactosi 1g/L, urea 1g/L, Secondary ammonium phosphate 1g/L, potassium primary phosphate 0.1g/L, ferrous sulfate 0.1g/L, regulates pH to 2.In 250ml triangular flask, liquid amount is 50ml, 120 DEG C, sterilizing in 20 minutes.Get MorganellamorganiiCICC21517 glycerine pipe seed liquor 0.5mL to inoculate, leavening temperature 35 DEG C, shaking speed 200rpm.After cultivating 24, by centrifugal for fermented liquid (rotating speed 10000rpm, time 10min), remove supernatant liquor and obtain thalline, the thalline sterile water wash of centrifugal acquisition twice.Get 0.1g wet thallus and put into the 2ml solution that L-Trp concentration is 2g/L, and regulate pH to 2, mix.Static conversion 24 hours in 37 DEG C of anaerobic culture boxes, filtering with microporous membrane conversion fluid, in liquid-phase chromatographic analysis conversion fluid, R-(-)-indoles-3-lactic acid concn is 0.4g/L and L-Trp residual quantity is 1.1g/L.
Embodiment 9
Substratum consists of: glucose 1g/L, peptone 1g/L, Secondary ammonium phosphate 1g/L, magnesium sulfate 0.1g/L, ferrous sulfate 0.1g/L, and L-Trp 10g/L regulates pH to 8.In 250ml triangular flask, liquid amount is 50ml, 120 DEG C, sterilizing in 20 minutes.Get MorganellamorganiiCICC21517 glycerine pipe seed liquor 0.5mL to inoculate, leavening temperature 35 DEG C, shaking speed 200rpm.After cultivating 24, filtering with microporous membrane conversion fluid, in liquid-phase chromatographic analysis conversion fluid, R-(-)-indoles-3-lactic acid concn is 2.3g/L and L-Trp residual quantity is 3.1g/L.
Embodiment 10
Substratum consists of: glucose 1g/L, urea 1g/L, Secondary ammonium phosphate 1g/L, potassium primary phosphate 0.1g/L, magnesium sulfate 0.1g/L, ferrous sulfate 0.1g/L, regulates pH to 8.In 500ml triangular flask, liquid amount is 100ml, 120 DEG C, sterilizing in 20 minutes, totally 10 bottles.Respectively get MorganellamorganiiCICC21517 glycerine pipe seed liquor 0.5mL to inoculate, leavening temperature 35 DEG C, shaking speed 200rpm.After cultivating 24, by centrifugal for fermented liquid (rotating speed 10000rpm, time 10min), remove supernatant liquor and obtain thalline, the thalline sterile water wash of centrifugal acquisition twice.Get 5g wet thallus and put into the 10ml solution that L-Trp concentration is 3g/L, and regulate pH to 5, mix.In 35 DEG C of shaking tables vibration (100rpm) after 1 hour, filtering with microporous membrane conversion fluid, in liquid-phase chromatographic analysis conversion fluid, R-(-)-indoles-3-lactic acid concn is 1.1g/L and L-Trp residual quantity is 1.2g/L.
Embodiment 11
Substratum consists of: glucose 10g/L, peptone 1g/L, Secondary ammonium phosphate 1g/L, potassium primary phosphate 0.1g/L, magnesium sulfate 0.1g/L, ferrous sulfate 0.1g/L, pH to 5.In 250ml triangular flask, liquid amount is 50ml, 120 DEG C, sterilizing in 20 minutes.Get Morganellamorganiisubsp.siboniiATCC49948 glycerine pipe seed liquor 0.5mL to inoculate, leavening temperature 35 DEG C, shaking speed 200rpm.After cultivating 24, filtering with microporous membrane conversion fluid, in liquid-phase chromatographic analysis fermented liquid, R-(-)-indoles-3-lactic acid concn is 0.006g/L.
Claims (4)
1. Morganella microbial transformation L-Trp produces R-(-)-indoles-3-lactic acid, and concrete microorganism has: Mo Genmo root fungus, the cold-resistant root fungus that rubs, Mo Genmo root fungus rub root subspecies and Mo Genmo root fungus Xi Baini subspecies.
2. the bacterial classification according to right 1, its culturing process also can be carried out at good oxygen condition at anaerobic state.
3. the thalline that the cultivation according to right 2 obtains, it transforms L-Trp and also can carry out at good oxygen condition at anaerobic state.
4. directly can add L-Trp length of side thalline limit in the yeast culture process according to right 2 and transform production R-(-)-indoles-3-lactic acid.
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| CN101374954A (en) * | 2005-04-26 | 2009-02-25 | 嘉吉有限公司 | Polypeptides and biosynthetic pathways for the production of monatin and its precursors |
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| CN101374954A (en) * | 2005-04-26 | 2009-02-25 | 嘉吉有限公司 | Polypeptides and biosynthetic pathways for the production of monatin and its precursors |
Non-Patent Citations (2)
| Title |
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| HANS E.MÜLLER: "Production and degradation of indole by gram-negative bacteria", 《ZBL. BAKT. HYG. A》 * |
| HARTMUT DRECHSEL等: "a-Keto Acids Are Novel Siderophores in the Genera Proteus,Providencia, and Morganella and Are Produced by Amino Acid Deaminases", 《JOURNAL OF BACTERIOLOGY》 * |
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