CN101363030B - Method for preparing 2-phenethyl alcohol by coupling yeast transformation and resin adsorption - Google Patents
Method for preparing 2-phenethyl alcohol by coupling yeast transformation and resin adsorption Download PDFInfo
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- CN101363030B CN101363030B CN200810071807A CN200810071807A CN101363030B CN 101363030 B CN101363030 B CN 101363030B CN 200810071807 A CN200810071807 A CN 200810071807A CN 200810071807 A CN200810071807 A CN 200810071807A CN 101363030 B CN101363030 B CN 101363030B
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Abstract
The invention provides a method for preparing 2-phenethyl alcohol by yeast transformation and resin adsorption coupling, which adopts yeast as a biocatalyst, takes L-phenyl alanine as substrate, and uses resin as product separating medium; ventilation, stirring and transformation are carried out, and the generation of ethanol is inhibited by controlling the accelerated velocity of glucose flow; the temperature of inversion is controlled within the range of 25-36 DEG C, the pH value ranges from 4 to 7, the transformation time is 10-100h, and natural 2-phenethyl alcohol is obtained by the post treatment of transformation liquid and the resin; the method eliminates the inhibited effect of the 2-phenethyl alcohol on the biocatalyst, and realizes that the target product 2-phenethyl alcohol is separated from zymotic fluid, so that the production efficiency and the separation efficiency are obviously improved, the cost for separation and purification is reduced, and the commercial process of transforming and synthesizing the 2-phenethyl alcohol by microorganism is realized.
Description
Technical field
The present invention relates to biotechnology and technical field, more specifically relate to the method for a kind of yeast conversion and resin absorption preparing 2-phenethyl alcohol coupling.
Background technology
2 phenylethyl alcohol is bata-phenethyl alcohol again, is a kind of aromatic alcohol with Rose Essentielle, is widely used in detergents and cosmetic and foodstuffs industry, is the maximum rose scent prescription of consumption in the makeup.At present, nearly ten thousand tons of the YO of global 2 phenylethyl alcohol, the overwhelming majority all is to adopt chemical synthesis process production, only has seldom a part from natural rose oil, extract.The 2 phenylethyl alcohol that adopts chemical synthesis process to produce often contains the by product that some are difficult to remove.These by products like diphenyl, β-chloro ethylbenzene, glycol chlorohydrin etc., have unpleasant odor, or even to the deleterious carcinogenic substance of HUMAN HEALTH.The drawback of chemosynthesis product is obvious.Along with growth in the living standard with to the concern of health, People more and more is paid attention to the security of food, more advocates " green " and " natural ".The law of various countries has carried out more strict restriction to the additive of chemosynthesis, and the production of foods and cosmetics more and more tends to use natural product.At US and European, the product that is labeled as " natural " must be the product that adopts physical method from natural materials, to extract or adopt mikrobe and enzymes biocatalysis conversion method to produce.On American market, the 2 phenylethyl alcohol market value of chemosynthesis is about 3.50$/kg, and natural 2 phenylethyl alcohol price is up to more than the 1000$/kg, and supply falls short of demand.
Utilize mikrobe synthetic method can produce natural 2 phenylethyl alcohol on a large scale.Microbial transformation Synthetic 2-phenylethyl alcohol has advantages such as production cost is low, the cycle short, environmental pollution is few, finally will become the main flow that 2 phenylethyl alcohol is produced.
Many yeast have the ability of Synthetic 2-phenylethyl alcohol, but yeast self Synthetic 2-phenylethyl alcohol concentration ratio is lower, and industrial prospect is little, and are substrate with the L-phenylalanine(Phe), then have very big feasibility by yeast cell bio-transformation synthesis of natural 2 phenylethyl alcohol.Yet; 2 phenylethyl alcohol has big toxicity to yeast cell, thereby when the 2 phenylethyl alcohol in the fermented liquid is accumulated to finite concentration, and yeast cell will inactivation; No longer carry out conversion reaction; 2 phenylethyl alcohol concentration in the fermented liquid is very low, increases the cost of follow-up separation and purification greatly, is difficult to carry out suitability for industrialized production.
Product original position transfer techniques (insitu product removal is called for short ISPR) is to solve the effective means that product suppresses.Product original position transfer techniques is exactly during the fermentation, adopts separation methods such as extraction, absorption, filtration to remove product, suppresses thereby reduce product, enhances productivity.Existing 2-phenylethyl alcohol bio-transformation ISPR technology adopts the method for organic solvent extraction to remove product more; Its shortcoming is at the biotransformation organic solvent biological catalyst to be had toxicity; And be prone to and emulsifying water, increase the difficulty of follow-up product separation and purification operation.
Summary of the invention
The object of the present invention is to provide the method for a kind of yeast conversion and resin absorption preparing 2-phenethyl alcohol coupling; This method is removed the restraining effect of 2 phenylethyl alcohol to biological catalyst; Realize the separation of title product 2 phenylethyl alcohol from fermented liquid; Significantly improve production efficiency and separation efficiency, reduce the cost of separation and purification, and realize the suitability for industrialized production of microbial transformation Synthetic 2-phenylethyl alcohol.
The method of yeast conversion of the present invention and resin absorption preparing 2-phenethyl alcohol coupling: the employing yeast is a biological catalyst, is substrate with the L-phenylalanine(Phe), is the product separating medium with the macroporous resin; Aeration-agitation transforms; And through the generation of control glucose stream rate of acceleration inhibition alcoholic acid, 25～36 ℃ of control invert points, pH4～7; Transform 10～100h, conversion fluid and resin make natural 2 phenylethyl alcohol through aftertreatment.
Remarkable advantage of the present invention is: the present invention produces in the process of 2 phenylethyl alcohol in yeast conversion; Adopt biosynthesizing-ISPR coupling technology, 2 phenylethyl alcohol is moved away from the biological respinse system, both removed the restraining effect of 2 phenylethyl alcohol biological catalyst; Realized the separation of title product 2 phenylethyl alcohol from fermented liquid again; Significantly improve production efficiency and separation efficiency, reduce the cost of separation and purification, and realize the suitability for industrialized production of microbial transformation Synthetic 2-phenylethyl alcohol.
Embodiment
(1) slant activation: yeast-inoculated in slant medium, in 25～32 ℃ of constant temperature culture 24～36h, is obtained the slant activation bacterial classification.Said slant medium consists of: glucose 10～30g/L, KH
2PO
41g/L, yeast extract powder 2～5g/L, agar 15～20g/L, solvent are water, the pH nature.
(2) seed enlarged culturing: the slant activation bacterial classification in the step (1) is seeded to seed culture medium with the inoculum size of 2～3 ring/30～50mL substratum,, obtains primary seed solution in 25～32 ℃, 150～250rpm shaking culture, 18～26h; Again primary seed solution is seeded to secondary seed medium with the inoculum size of 5～10% volume ratios,, obtains secondary seed solution in 25～32 ℃, 150～250rpm shaking culture, 18～26h.Said first order seed substratum or secondary seed medium consist of: glucose 20～50g/L, KH
2PO
41g/L, yeast extract powder 1～3g/L, urea 2～5g/L, solvent are water, the pH nature.
(3) bio-transformation: the secondary seed solution in the step (2) is seeded to the conversion substratum with the inoculum size of 1-10% volume ratio, aeration-agitation, the control dissolved oxygen is greater than 0.5mg/L; 25～36 ℃ of controlled temperature; After controlling pH4～7,2 hour with soda acid, add 1～20g/LL-phenylalanine(Phe); And adding glucose with suitable data rate stream, the concentration of glucose is controlled at 0.01～20.0g/L.Said conversion substratum consists of: glucose 20～40g/L, KH
2PO
41g/L, urea 2～4g/L, MgSO
40.3～0.5g/L, CaCl
20.2g/L solvent is a water, the pH nature.
(4) the product original position shifts: add macroporous adsorbent resin, add-on is 10～300g/L; Also can resin be loaded into post, fermented liquid squeezed into resin column and effluent is inserted fermentor tank formation circulation again through pump; Fermented liquid also can with the filtered solution upper prop, be crossed post liquid and can all or part ofly be returned fermentor tank formation circulation earlier behind membrane separation unit separating thallus and solid substance.New resin after resin absorption is saturated after the replaceable regeneration.Oxyty, pH and mend control condition such as sugared speed with (3); Can suitably add the L-phenylalanine(Phe) in conversion process; Transforming 10～100h stops.
(5) resin aftertreatment: from fermented liquid, take out resin, load into post,, collect the 2 phenylethyl alcohol elution peak, make the high-purity natural 2 phenylethyl alcohol through rectifying again with finite concentration ethanol dynamic desorption.
The present invention adopts the yeast with Emhorn approach, like yeast saccharomyces cerevisiae (Saccharomyces cerevisiae), Saccharomyces aceti (Saccharomyces vini), product protein torulopsis (Torulopsis utilis), Kluyveromyces lactis (Kluyveromyces lactis), unusual debaryomyces hansenii (Hansenulaanom ala), kluyveromyces marxianus (Kluyveromyces marxianus), fermentation pichia spp (Pichia fermentans) etc.
The consumption of macroporous adsorbent resin of the present invention and fermented liquid amount ratio are 10～300g: 1L the present invention adopts hollow-fibre membrane or the ceramic membrane of aperture 0.1-1.2 μ m for the fermented liquid membrane sepn.
The condition of resin aftertreatment is: with 30-100% (v/v) ethanol elution resin, collect the phenylethyl alcohol elution peak, and then rectifying obtains the high purity 2 phenylethyl alcohol.
Below in conjunction with specific examples the present invention is further described, but protection scope of the present invention is not limited thereto.
Embodiment 1
The present embodiment culture medium prescription is:
Slant medium: glucose 10g/L, KH
2PO
41g/L, yeast extract powder 4g/L, agar 20g/L, solvent are water, the pH nature.
Seed culture medium: glucose 20g/L, KH
2PO
41g/L, yeast extract powder 2g/L, urea 2g/L, solvent are water, the pH nature.
Transform substratum: glucose 20g/L, KH
2PO
41g/L, urea 4g/L, MgSO
40.5g/L, CaCl
20.2g/L solvent is a water, the pH nature.
Above substratum is all at 115 ℃ of sterilization 20min.
Choose one from refrigerator preservation yeast inclined-plane earlier and completely encircle thalline, be inoculated in fresh slant medium, behind 30 ℃ of constant temperature culture 30h, obtain activatory yeast inclined-plane.Choose two ring thalline from activatory yeast inclined-plane, be inoculated in the 250mL triangular flask that the 40mL seed culture medium is housed,, obtain primary seed solution in 30 ℃, 200rpm shaking culture 24h.To the 500mL triangular flask that the 80mL seed culture medium is housed,, obtain secondary seed solution with aseptic pipette, extract 5mL primary seed solution in 30 ℃, 250rpm shaking culture 20h.
Get the 300mL secondary seed solution and be inoculated in the 5L fermentor tank that 2.7L conversion substratum is housed, 30 ℃ of controlled temperature stir 300rpm; Ventilation 2vvm with 1mol/L HCl or NaOH control pH5.0, adds 40g L-phenylalanine(Phe) behind the 2h; Add the glucose of 600g/L with the data rate stream of 4g/ (Lh), add the 300g macroporous adsorbent resin behind the reaction 4h, react 15h and add 30g L-phenylalanine(Phe) again; React 30h and finish reaction, fermentating liquid volume is 3.05L; Take out resin, water flush away yeast is used 95% ethanol elution again; Collect the 2 phenylethyl alcohol elution peak; Fermented liquid is centrifugal remove yeast after, transfer pH9～10, separate 2 phenylethyl alcohol with macroporous resin adsorption; Finally can obtain the 2 phenylethyl alcohol of 38.8g, total molar yield that the L-phenylalanine(Phe) is converted into 2 phenylethyl alcohol reaches 0.92.
Embodiment 2
The present embodiment culture medium prescription is:
Slant medium: glucose 10g/L, KH
2PO
41g/L, yeast extract powder 4g/L, agar 20g/L, solvent are water, the pH nature.
Seed culture medium: glucose 20g/L, KH
2PO
41g/L, yeast extract powder 3g/L, urea 2g/L, solvent are water, the pH nature.
Transform substratum: glucose 30g/L, KH
2PO
41g/L, urea 3g/L, MgSO
40.4g/L, CaCl
20.2g/L solvent is a water, the pH nature.
Above substratum is all at 115 ℃ of sterilization 20min.
Choose one from refrigerator preservation yeast inclined-plane earlier and completely encircle thalline, be inoculated in fresh slant medium, behind 30 ℃ of constant temperature culture 30h, obtain activatory yeast inclined-plane.Choose two ring thalline from activatory yeast inclined-plane, be inoculated in the 250mL triangular flask that the 40mL seed culture medium is housed,, obtain primary seed solution in 30 ℃, 200rpm shaking culture 22h.To the 500mL triangular flask that the 80mL seed culture medium is housed,, obtain secondary seed solution with aseptic pipette, extract 5mL primary seed solution in 30 ℃, 250rpm shaking culture 18h.
Get the 300mL secondary seed solution and be inoculated in the 5L fermentor tank that 2.7L conversion substratum is housed, 30 ℃ of controlled temperature stir 400rpm; Ventilation 2vvm with 1mol/L HCl or NaOH control pH4.0, adds 45g L-phenylalanine(Phe) behind the 2h; Add the glucose of 600g/L with the data rate stream of 10g/ (Lh), add the 300g macroporous adsorbent resin behind the reaction 5h, react 18h and add 30g L-phenylalanine(Phe) again; 28h changes the equivalent regenerating resin; Add 30g L-phenylalanine(Phe) simultaneously, 43h finishes reaction, fermented liquid final volume 3.03L.Yeast on the water flush away resin is used 95% ethanol elution again, collects the 2 phenylethyl alcohol elution peak.Fermented liquid is centrifugal remove yeast after, transfer pH9～10, separate 2 phenylethyl alcohol with macroporous resin adsorption, finally can obtain the 61.5g2-phenylethyl alcohol, total molar yield that the L-phenylalanine(Phe) is converted into 2 phenylethyl alcohol reaches 0.91.
Embodiment 3
The present embodiment culture medium prescription is:
Slant medium: glucose 10g/L, KH
2PO
41g/L, yeast extract powder 3g/L, agar 20g/L, solvent are water, the pH nature.
Seed culture medium: glucose 30g/L, KH
2PO
41g/L, yeast extract powder 2g/L, urea 3g/L, solvent are water, the pH nature.
Transform substratum: glucose 40g/L, KH
2PO
41g/L, urea 3g/L, MgSO
40.3g/L, CaCl
20.2g/L solvent is a water, the pH nature.
Above substratum is all at 115 ℃ of sterilization 20min.
Choose one from refrigerator preservation yeast inclined-plane earlier and completely encircle thalline, be inoculated in fresh slant medium, behind 30 ℃ of constant temperature culture 30h, obtain activatory yeast inclined-plane.Choose two ring thalline from activatory yeast inclined-plane, be inoculated in the 250mL triangular flask that the 40mL seed culture medium is housed,, obtain primary seed solution in 30 ℃, 200rpm shaking culture 20h.To the 500mL triangular flask that the 80mL seed culture medium is housed,, obtain secondary seed solution with aseptic pipette, extract 5mL primary seed solution in 30 ℃, 250rpm shaking culture 24h.
Get the 1L secondary seed solution and be inoculated in the 20L fermentor tank that 11L conversion substratum is housed, 30 ℃ of controlled temperature stir 500rpm; Ventilation 2.5vvm with 1mol/L HCl or NaOH control pH5.5, adds 180g L-phenylalanine(Phe) behind the 2h; Add the glucose of 600g/L with the data rate stream of 8g/ (Lh), behind the reaction 12h fermented liquid is pumped into the ceramic membrane tripping device, cleaner liquid pumps into the pillar that the 1200g macroporous adsorbent resin is housed; Cross post liquid and contain yeast refluxing liquid blowback fermentor tank with the ceramic membrane tripping device; React 20h and add 120g L-phenylalanine(Phe) again, 28h changes the equivalent regenerating resin, adds 120g L-phenylalanine(Phe) simultaneously; 45h finishes reaction, final fermentating liquid volume 12.3L.With 95% ethanol elution resin, collect the 2 phenylethyl alcohol elution peak, fermented liquid is centrifugal remove yeast after; Transfer pH9～10; Separate 2 phenylethyl alcohol with macroporous resin adsorption, finally can obtain the 241g2-phenylethyl alcohol, total molar yield that the L-phenylalanine(Phe) is converted into 2 phenylethyl alcohol reaches 0.90.
Claims (6)
1. the method for yeast conversion and resin absorption preparing 2-phenethyl alcohol coupling, it is characterized in that: the employing yeast is a biological catalyst, is substrate with the L-phenylalanine(Phe); With the resin is the product separating medium, and aeration-agitation transforms, and generates through control glucose stream rate of acceleration inhibition alcoholic acid; 25～36 ℃ of control invert points; PH4～7 transform 10～100h, and conversion fluid and resin make natural 2 phenylethyl alcohol through aftertreatment; Its preparation process is:
(1) yeast culture: carry out the seed enlarged culturing after the inoculation of yeast process, the slant activation and become secondary seed solution;
(2) bio-transformation: secondary seed solution is seeded to the conversion substratum, aeration-agitation, the control dissolved oxygen is greater than 0.5mg/L; 25～36 ℃ of temperature; After controlling pH4～7,2 hour with soda acid, add the L-phenylalanine(Phe) to concentration 1～20g/L; And add glucose with suitable data rate stream, make the concentration that transforms the glucose in the solution be controlled at 0.01～20.0g/L; Said conversion substratum consists of: glucose 20～40g/L, KH
2PO
41g/L, urea 2～4g/L, MgSO
40.3～0.5g/L, CaCl
20.2g/L solvent is a water, the pH nature;
(3) the product original position shifts: add macroporous resin in the yeast culture process, add-on is 50～300g/L fermented liquid; Perhaps resin is loaded into post, fermented liquid is squeezed into resin column and effluent is inserted fermentor tank formation circulation again through pump; Perhaps that fermented liquid is first behind membrane separation unit separating thallus and solid substance, with the filtered solution upper prop, cross all or part of fermentor tank that returns of post liquid and form circulation; Replaceable new resin after resin absorption is saturated; Oxyty, pH and mend control condition such as sugared speed with (2); Can suitably add the L-phenylalanine(Phe) in conversion process; Transforming 10～100h stops;
(4) resin aftertreatment: from fermented liquid, take out resin, load into post,, collect the 2 phenylethyl alcohol elution peak, make the high-purity natural 2 phenylethyl alcohol through rectifying again with finite concentration ethanol dynamic desorption.
2. the method for yeast conversion according to claim 1 and resin absorption preparing 2-phenethyl alcohol coupling is characterized in that: said yeast adopts the yeast with Emhorn approach.
3. the method for yeast conversion according to claim 1 and resin absorption preparing 2-phenethyl alcohol coupling is characterized in that: said yeast adopts a kind of in yeast saccharomyces cerevisiae, Saccharomyces aceti, product protein torulopsis, Kluyveromyces lactis, unusual debaryomyces hansenii, kluyveromyces marxianus or the fermentation pichia spp.
4. the method for yeast conversion according to claim 1 and resin absorption preparing 2-phenethyl alcohol coupling is characterized in that: said resin is a macroporous adsorbent resin; The consumption of said macroporous adsorbent resin and fermented liquid amount ratio are 10～300g: 1L.
5. the method for yeast conversion according to claim 1 and resin absorption preparing 2-phenethyl alcohol coupling is characterized in that: membrane sepn adopts hollow-fibre membrane or the ceramic membrane of aperture 0.1-1.2 μ m in the said step (3).
6. the method for yeast conversion according to claim 1 and resin absorption preparing 2-phenethyl alcohol coupling; It is characterized in that: the condition of the resin aftertreatment of said step (4) is: with 30～100% (v/v) ethanol elution resin; Collect the phenylethyl alcohol elution peak, and then rectifying obtains high-purity benzene ethanol.
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Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101857844B (en) * | 2009-04-10 | 2012-03-21 | 上海凯信生物科技有限公司 | Wine brewing yeast strain capable of generating 2-phenethyl alcohol by biotransformation of L-phenylanine |
| CN101864456B (en) * | 2009-04-17 | 2012-09-05 | 上海凯信生物科技有限公司 | Method for carrying out bioconversion on L-phenylalanine to produce 2-phenethyl alcohol |
| CN103509843A (en) * | 2012-06-29 | 2014-01-15 | 江苏天晟药业有限公司 | Method for high-yield preparation of glycyrrhetinic acid monoglucuronide |
| CN104561135B (en) * | 2013-10-15 | 2020-06-26 | 丰益(上海)生物技术研发中心有限公司 | Method for producing aromatic substance by trichoderma reesei |
| CN105707203B (en) * | 2016-03-07 | 2019-10-01 | 江西省科学院微生物研究所 | A kind of preparation method and applications method of the fresh-keeping preparation of livestock and poultry fish |
| CN107446813B (en) * | 2017-08-22 | 2023-10-31 | 江西省科学院微生物研究所 | Device for producing 2-PE through continuous conversion and method for producing 2-PE through continuous conversion |
| CN110904160B (en) * | 2019-11-12 | 2022-04-22 | 万华化学集团股份有限公司 | Fermentation method for increasing beta-phenethyl alcohol unit yield |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5919991A (en) * | 1996-07-03 | 1999-07-06 | Subbiah; Ven | Solid phase extraction of phenethyl alcohol |
| CN1403581A (en) * | 2002-10-22 | 2003-03-19 | 华宝香化科技发展（上海）有限公司 | Microbe fermenting process of producing perfume phenylethanol |
| CN101157940A (en) * | 2007-09-21 | 2008-04-09 | 浙江工业大学 | Method for preparing natural 2-benzyl carbinol |
-
2008
- 2008-09-18 CN CN200810071807A patent/CN101363030B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5919991A (en) * | 1996-07-03 | 1999-07-06 | Subbiah; Ven | Solid phase extraction of phenethyl alcohol |
| CN1403581A (en) * | 2002-10-22 | 2003-03-19 | 华宝香化科技发展（上海）有限公司 | Microbe fermenting process of producing perfume phenylethanol |
| CN101157940A (en) * | 2007-09-21 | 2008-04-09 | 浙江工业大学 | Method for preparing natural 2-benzyl carbinol |
Non-Patent Citations (1)
| Title |
|---|
| 刘东亚.微生物转化发酵法生产天然香料β-苯乙醇的研究.《中国优秀硕士学位论文全文数据库(电子期刊)工程科技Ⅰ辑》.2007,1-50. * |
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