CN105543291A - Microbial transformation method - Google Patents
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Abstract
The invention relates to a method for producing R-(+)-2-hydroxy-3-phenylpropanoic acid by transforming L-phenylalanine by adopting providencia microbes. The method is simple in process and has important industrial application value.
Description
Technical field
The present invention adopts Providence bacterium to transform L-Phe and produces D-phenyllactic acid, belongs to industrial microorganism field.
Background technology
D-phenyllactic acid, formal name used at school R-(+)-PLA, English by name: R-(+)-2-hydroxy-3-phenylpropanoicacid, D-(+)-3-Phenyllacticacid.
Phenyllactic acid is that discovered in recent years can secrete by part milk-acid bacteria a kind of New Biological Preservatives produced.It has D-phenyllactic acid and L-phenyllactic acid two kinds of mapping allosome bodies, effectively can suppress multiple and cause the bacterium of food spoilage and toxigenic fungi.Research shows that the bacteriostasis of D-phenyllactic acid is a little more than L-phenyllactic acid.
As a kind of New Biological Preservatives, the phenyllactic acid using value that tool is important in the food industry.Current mainly through the production of large intestine genetic engineering bacterium expression lactic dehydrogenase enzymatic conversion phenyl-pyruvic acid, as Chinese patent CN201410818165.X, CN201410393768.X and CN201210338378.3.Also have and produced, as Chinese patent CN201510089823.0, CN201210005544.8 etc. by all kinds of lactic acid bacteria tranformation phenyl-pyruvic acid or phenylalanine.Also method (the EfficientConversionofPhenylpyruvicAcidtoPhenyllacticAcid byUsingWholeCellsofBacilluscoagulansSDM adopting genus bacillus to transform phenyl-pyruvic acid product phenyllactic acid is had, 2011, PLoSOne.6 (4): e19030).
Based on the significant application value of D-phenyllactic acid, this patent proposes Providence bacterium microorganism and transforms the scheme that L-Phe produces D-phenyllactic acid.L-Phe is current mainly through Production by Microorganism Fermentation, and abundant raw material is easy to get.
Providence bacterium (Providencia) is the gram negative bacterium that a class can make phenylalanine oxidative deamination.Existing main 8 kinds: produce alkali Providence (Providenciaalcalifaciens), providencia stuartii (Providenciastuartii), thunder pole Providence (Providenciarettgeri), insect Providence (Providenciavermicola), Providenciasneebia, Providenciaburhodogranariea.Providence bacterium has powerful oxidative deamination ability (SherrisMedicalMicrobiology, 2004,4thed.),
Pertinent literature thinks that L-Phe can only be oxidized to phenyl-pyruvic acid by these microorganisms, and phenyllactic acid (α-ketoacidsarenovelsiderophoresinthegeneraproteus cannot be reduced into further, providencia, andmorganellaandareproducedbyaminoaciddeaminases, 1993, Journalofbacteriology, 175 (9), 2727-2733), this may condition select improper relevant with it.
The present invention can be led to Providence bacteria microorganism and L-Phe be changed into optically pure D-phenyllactic acid.Although phenyl-pyruvic acid is more direct substrate, price is higher, and therefore L-Phe is best substrate.Providence bacterium is a kind of facultative anaerobe, can transform and produce D-phenyllactic acid, have high conversion and highly purified feature under anaerobic condition or aerobic condition.
Summary of the invention
The present invention is by cultivating Providence bacterium microorganism thalline, and transform L-Phe and produce D-phenyllactic acid, technical scheme is as follows:
1, bacterial strain
The present invention's bacterial strain used has the ProvidenciaalcalifaciensATCC9886 of purchased from American ATCC strain library, ProvidenciarustigianiiATCC33673, ProvidenciasneebiaATCCBAA-1589, ProvidenciarettgeriATCC29944, ProvidenciaheimbachaeATCC35613, ProvidenciastuartiiATCC33672, ProvidenciaburhodogranarieaATCCBAA-1590 and purchased from the ProvidenciarettgeriCICC10488 of Chinese industrial Microbiological Culture Collection administrative center and the ProvidenciavermicolaCCTCCAB205297 of China typical culture collection center.
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 D-phenyllactic acid is transformed
The scheme that conversion process adopts has 2 kinds:
(1) the liquid culturing process of cell, adds L-Phe substrate in above-mentioned culture system; L-Phe addition is 0-20g/L.
(2) liquid state fermentation culture centrifugal segregation fermented liquid is obtained thalline, the reactant aqueous solution system put into by thalline containing L-Phe substrate is carried out; Conversion process temperature 20-40 DEG C, pH2-8, transformation time 1-24 hour.In conversion fluid, L-Phe initial concentration is 0.1-20g/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 100 bottles, 120 DEG C, sterilizing in 20 minutes.Get ProvidenciarustigianiiATCC33673 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 40g wet thallus and put into the 1000ml solution that L-Phe concentration is 20g/L, mix.In 37 DEG C of shaking tables vibration (100rpm) after 48 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 D-phenyllactic acid concentration is 10.1g/L, and residue L-Phe concentration is 7.3g/L.Preparative chromatography is adopted to obtain 8.2g sterling.
Its specific rotation analyzed by polarimeter
nuclear magnetic data is: 1HNMR (CDCl
3600MHz): δ 7.33 (2H, dJ7.6Hz), 7.29 (1H, d, J7.6Hz), 7.24 (2H, d, J7.6Hz), 4.48 (1H, dd, J4.3,7.3Hz), 4.23 (2H, OHs, broad), 3.21 (1H, dd, J4.3,14.0Hz), 2.98 (1H, dd, J7.3,14.0Hz).13CNMR(CDCl
3,600MHz):δ177.57，135.93，129.52，129.53，128.54，128.64，127.13，71.12，40.13。The mass-spectrometric data of converted product is: (-ESI, negativemode) m/z:165.0 [M-1].
According to above data, determine that its molecule and optical texture and D-phenyllactic 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 ProvidenciarettgeriATCC29944 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-Phe 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 D-phenyllactic acid concentration is 0.5g/L, and residue L-Phe concentration is 1.1g/L.
Get ProvidenciarettgeriATCC29944 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-Phe 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 D-phenyllactic acid concentration is 0.6g/L, and residue L-Phe concentration is 1.2g/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 ProvidenciarettgeriCICC10488 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-Phe 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, D-phenyllactic acid concentration is 0.01g/L.
Embodiment 4
Substratum consists of: fructose 50g/L, ammonium sulfate 5g/L, Secondary ammonium phosphate 1g/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 ProvidenciaheimbachaeATCC35613 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-Phe 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, D-phenyllactic acid concentration is 0.5g/L and L-Phe residual quantity is 0.9g/L.
Embodiment 5
Substratum consists of: wood sugar 50g/L, ammonium sulfate 1g/L, potassium primary phosphate 1g/L, magnesium sulfate 0.2g/L, ferrous sulfate 0.1g/L.In 250ml triangular flask, liquid amount is 50ml, 120 DEG C, sterilizing in 20 minutes.Get ProvidenciavermicolaCCTCCAB205297 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-Phe 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, D-phenyllactic acid concentration is 0.2g/L and L-Phe residual quantity is 1.0g/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 ProvidenciavermicolaCCTCCAB205297 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-Phe 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, D-phenyllactic acid concentration is 0.5g/L and L-Phe residual quantity is 0.7g/L.
Embodiment 7
Substratum consists of: maltose 15g/L, ammonium chloride 1g/L, Secondary ammonium phosphate 1g/L, magnesium sulfate 0.1g/L, ferrous sulfate 0.1g/L, regulates pH to 5.In 250ml triangular flask, liquid amount is 50ml, 120 DEG C, sterilizing in 20 minutes.Get ProvidenciaalcalifaciensATCC9886 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-Phe concentration is 3g/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, D-phenyllactic acid concentration is 0.6g/L and L-Phe residual quantity is 1.1g/L.
Embodiment 8
Substratum consists of: semi-lactosi 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 2.In 250ml triangular flask, liquid amount is 50ml, 120 DEG C, sterilizing in 20 minutes.Get ProvidenciasneebiaATCCBAA-1589 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-Phe 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, D-phenyllactic acid concentration is 0.1g/L and L-Phe residual quantity is 1.4g/L.
Embodiment 9
Substratum consists of: glucose 1g/L, peptone 1g/L, Secondary ammonium phosphate 1g/L, potassium primary phosphate 0.1g/L, ferrous sulfate 0.1g/L, and L-Phe 2g/L regulates pH to 8.In 250ml triangular flask, liquid amount is 50ml, 120 DEG C, sterilizing in 20 minutes.Get ProvidenciastuartiiATCC33672 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, D-phenyllactic acid concentration is 1.0g/L and L-Phe residual quantity is 0.1g/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, regulates pH to 8.In 500ml triangular flask, liquid amount is 100ml, 120 DEG C, sterilizing in 20 minutes, totally 10 bottles.Respectively get ProvidenciaburhodogranarieaATCCBAA-1590 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-Phe concentration is 20g/L, and regulate pH to 5, mix.In 35 DEG C of shaking tables vibration (100rpm) after 10 hours, filtering with microporous membrane conversion fluid, in liquid-phase chromatographic analysis conversion fluid, D-phenyllactic acid concentration is 9.3g/L and L-Phe residual quantity is 8.2g/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 ProvidenciaalcalifaciensATCC9886 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, D-phenyllactic acid concentration is 0.03g/L.
Claims (4)
1. Providence bacterium microorganism transforms L-Phe and produces R-(+)-PLA, and concrete microorganism has: produce alkali Providence, providencia stuartii, thunder pole Providence, insect Providence, Providenciasneebia, Providenciaburhodogranariea.
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-Phe and also can carry out at good oxygen condition at anaerobic state.
4. directly can add L-Phe length of side thalline limit in the yeast culture process according to right 2 and transform production R-(+)-PLA.
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| CN109781921A (en) * | 2019-03-22 | 2019-05-21 | 上海海洋大学 | A method of quickly detecting phenyllactic acid content using reversed-phased high performace liquid chromatographic |
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| 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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| CN109781921A (en) * | 2019-03-22 | 2019-05-21 | 上海海洋大学 | A method of quickly detecting phenyllactic acid content using reversed-phased high performace liquid chromatographic |
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