CN101096692A - Method for preparing gamma-decalactone and improving output by biotransformation and separated coupling - Google Patents
Method for preparing gamma-decalactone and improving output by biotransformation and separated coupling Download PDFInfo
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- CN101096692A CN101096692A CNA2007100240490A CN200710024049A CN101096692A CN 101096692 A CN101096692 A CN 101096692A CN A2007100240490 A CNA2007100240490 A CN A2007100240490A CN 200710024049 A CN200710024049 A CN 200710024049A CN 101096692 A CN101096692 A CN 101096692A
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- decalactone
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- viscotrol
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Abstract
The invention discloses a method for preparing gamma-decyl inner ester and biological transforming, separating and coupling and improving the yield in the technique field of preparing the aromatic compound with biological method. The invention provides a strain Yarrowia sp. CGMCC 2.1405 with the high-effective transformation ability, which improves the yield of gamma--decyl inner ester and achieves the separation of the product with the transformation, separation and coupling technique by culturing the cell, preparing the total cell multi-enzyme system, biological transformation of the total cell multi-enzyme system, adding the macroreticular adsorbing resin in the product transformation process. The invention reduces the product influence for the bacterial, which improves the yield, and achieves the effective original position separation of the product.
Description
Technical field
A kind of γ of preparation-decalactone and bio-transformation and the method for separating coupling raising output belong to the technical field that biological process prepares aromatic compound.The present invention relates to a kind of novel method that is used to prepare γ-decalactone.
Background technology
γ-decalactone (gamma decalactone) has another name called third decalactone, is the five-ring lactone compound.γ-decalactone is a kind of important aromatic compound because of its organ sensory characteristic becomes, it has fruity, peach sample fragrance and aromaticity, has typical coconut fragrance, fragrance is light than peach aldehyde, it is widely used at perfume industry with the characteristic of its tempting peach perfume and low fragrance threshold value, is mainly used in type essence such as preparation cream, peach, oranges and tangerines and coconut.In general, can produce γ-decalactone by fruit.Yet its content in fruit is few, makes to separate it economically by extraction or distillatory method.γ-the decalactone that extracts from fruit has specific three-dimensional arrangement, and chemical method production is raceme, does not find this kind spices as yet in a large number at occurring in nature.Along with the increase of people, utilize biological process production to have the concern that optically active γ-decalactone has attracted many researchists to γ-decalactone spice product demand.
At present, utilize biotechnology to obtain γ-decalactone: biosynthesizing (being mainly fungi fermentation production), bio-transformation and biocatalysis (lipase-catalyzed) by 3 kinds of approach.And most probable realizes that the method for industrialization is to utilize microorganism to carry out bio-transformation at present.The conversion of substrate of this method mainly contains: hydroxy fatty acid, non-hydroxyl lipid acid and fatty acid ester.The direct precursor of gamma lactone is γ-hydroxy fatty acid, and different lipid acid substrates generate direct precursor through microbial transformation earlier, change into corresponding lactone again, and just the multienzyme of microorganism transforms.Common microorganism comprises bacterium, yeast or fungi, utilizes natural hydroxy fatty acid, as is present in the ricinoleic acid (ricinoleic acid) in the Viscotrol C, in the microbial transformation process, through β-Yang Hua, chain length is shortened earlier, change into γ-decalactone again.Utilizing non-hydroxyl lipid acid to transform production γ-decalactone also has many reports, does not illustrate fully as yet but microbial transformation lipid acid forms the pathways metabolism and the regulation mechanism of lactone, and conversion process is also comparatively complicated.
Therefore, carried out a large amount of trials in recent years and prepared γ-decalactone with biotechnological means.Major part method uses each primary yeast to carry out.
Summary of the invention
(1) technical problem that will solve
The object of the present invention is to provide a kind of γ of preparation-decalactone and bio-transformation and the method for separating coupling raising output.Bio-transformation and separation conversion coupling technique by full cell multi-enzyme system prepare γ-decalactone, and not only can reduce product influences thalline, thereby improves output, and makes things convenient for the extraction of product, realizes that effective original position of product is separated.
(2) technical scheme
A kind of method for preparing γ-decalactone, use is separated multiple film spore yeast Yarrowia lipolyticaCGMCC 2.1405 cultures of fat and is carried out bio-transformation, be substrate with the Viscotrol C in the product conversion process, add macroporous adsorbent resin with transforming with separation coupling technology raising γ-decalactone output and realizing separating of product;
1. starting strain: separate the multiple film spore yeast Yarrowia lipolytica CGMCC 2.1405 of fat;
2. cell cultures:
Substratum is: glucose 10～20g/L, yeast extract paste 1～5g/L, Secondary ammonium phosphate 10～15g/L, KH
2PO
41～10g/L, MgSO
47H
2O 0.1～1g/L, tween-80 0.1～5g/L, initial pH6～9;
Culture condition:, cultivate 12～36h under 100～200r/min condition at 20～40 ℃;
3. transform and separation coupling technology: add Viscotrol C 20～30g/L behind strain culturing 12～36h, add macroporous adsorbent resin 60～100g/L, pH7.5, continues to transform 48～60h again by 20～40 ℃ under the condition of 100～200r/min.
Big pore adsorption resin is the AB-8 resin, and this resin absorption converted product is with the toxicity of reduction high density product to yeast cell, and then raising output.Can reuse after the used resin regeneration.
The present invention is at first from microorganism, and screening obtains better transforming the microorganism yeast of γ-decalactone, utilizes yeast, is substrate with the main ingredient ricinoleic acid in the Viscotrol C, through β-Yang Hua carbochain is shortened, and lactonizing generates γ-decalactone again.Adopt resin absorption technology continuous adsorption converted product, when reducing the inhibition and murder by poisoning of end product, improve transformation efficiency, also reduced difficulty for downstream processing to microorganism or enzyme.
Conversion with separate coupling: when adding Viscotrol C and beginning to transform, add Resin A B-8 simultaneously, control conversion reaction pH is 7.5, can keep higher relatively specific production rate for a long time, help the accumulation of product, show that conversion-adsorbing coupled technology is fit to the production of γ-decalactone, can increase substantially output.
Resin regeneration: the Resin A B-8 that transforms after finishing carries out manipulation of regeneration, can be reused for conversion.In container, add 3%～5% hydrochloric acid soln that is higher than resin layer 10cm and soak 2h～4h, drip washing through post.Continue with 3%～5% hydrochloric acid soln through post of 3～4 times of resin volumes, be washed near neutral; Soak 4h with 3%～5% sodium hydroxide solution, the drip washing through post with 3%～5% sodium hydroxide solution through post of 3～4 times of resin volumes, cleans to the pH value with water purification and is neutrality, and is standby.
(3) beneficial effect
The invention provides bacterial strain and separate the multiple film spore yeast Yarrowia sp.CGMCC 2.1405 of fat with efficient conversion capability, preparation by cell cultures and full cell multi-enzyme system, with the Viscotrol C is substrate, and bio-transformation by full cell multi-enzyme system and conversion and separation coupling technology prepare γ-decalactone.After utilizing resin absorption γ-decalactone to be coupled to transform, ultimate production reaches 2.17g/L, and influence improves output to thalline not only can to reduce product, and make things convenient for the extraction of product, realize effective original position separation of product, can reuse after the resin regeneration to have excellent industrial application foreground.
Description of drawings
The different addition manners of Fig. 1 Viscotrol C are to the influence of the conversion of γ-decalactone.
The influence that Fig. 2 different resins addition transforms γ-decalactone.
The influence of Fig. 3 Viscotrol C concentration to transforming.
Fig. 4 Resin A B-8 transforms the conditional curve that separates Fourier Series expansion technique.
Embodiment
Following examples bacterial strain uses therefor and cell cultures are described according to technique scheme, and the influence factor of conversion with separation coupling technology is exemplified below.
The influence that the different addition manners of embodiment 1 Viscotrol C transform γ-decalactone.
Contrast the grown cell culture method and with the Viscotrol C be two kinds of different preparation methods of carbon source direct fermentation.Grown cell transforms, and promptly after thalli growth glucose to the balance period exhausts substantially, directly adds Viscotrol C, makes microorganism carry out bio-transformation when breeding is grown.The employing process of growth transforms, and decalactone output was obviously higher after the adding Viscotrol C transformed 48h.When being carbon source direct fermentation, also can prepare product, but output is lower with the Viscotrol C.The result as shown in Figure 1.
Embodiment 2 different resins additions are to the influence of the conversion yield of γ-decalactone.
Add Resin A B-8, addition (g/L) is respectively 25,50,75,100,125, and the conversion situation of γ-decalactone as shown in Figure 2.Along with the increase of amount of resin, its adsorptive capacity to γ-decalactone progressively rises, and the resin dosage is that 75 o'clock total concentration are the highest, reaches 1.73g/L, continues to increase resin demand, and overall productivity does not obviously improve.
The influence that embodiment 3 different Viscotrol C consumptions transform γ-decalactone.
Amount of resin is constant, adds after different castor-oil plant oil masses transform, and measures γ-decalactone content, the results are shown in Figure 3.Decalactone output was higher when as seen from Figure 3, concentration of substrate was 25g/L.There is optimum value in the substrate dosage, and along with the increase of concentration of substrate, output then can descend thereafter.
The resin content of 75g/L, Viscotrol C concentration are 25g/L, and the conversion process curve of this moment as shown in Figure 4.As seen from Figure 4, add resin after, γ-decalactone output reaches maximum value 2.17g/L at 56h, and does not add resin and compares output and improve 92%.Add resin, transformation system can be kept higher relatively specific production rate for a long time, helps the accumulation of product, and this shows that conversion-fractionation by adsorption coupling technique is fit to the production of γ-decalactone, can increase substantially output.
Embodiment 5 regeneration of resin utilizations.
The Resin A B-8 that transforms after finishing carries out manipulation of regeneration, drops into again to transform, and changing effect is as shown in table 1.As seen, use regenerating resin little, show that reground resin changes not quite the adsorptive power of γ-decalactone, can repeatedly reuse, but resin quantity has certain loss in operation the ultimate capacity influence.
The repetition profit of table 1 regenerating resin
| The resin regeneration number of times | 1 | 2 | 3 | 4 |
| γ-decalactone total concn (g/L) resin quality reclamation rate % | 2.17 92.1 | 2.03 85.6 | 2.02 79.1 | 1.91 70.3 |
Claims (3)
1. method for preparing γ-decalactone, it is characterized in that using and separate multiple film spore yeast Yarrowialipolytica CGMCC 2.1405 cultures of fat and carry out bio-transformation, be substrate with the Viscotrol C in the product conversion process, add macroporous adsorbent resin with transforming with separation coupling technology raising γ-decalactone output and realizing separating of product;
(1) starting strain: separate the multiple film spore yeast Yarrowia lipolytica CGMCC 2.1405 of fat;
(2) cell cultures:
Substratum is: glucose 10～20g/L, yeast extract paste 1～5g/L, Secondary ammonium phosphate 10～15g/L, KH
2PO
41～10g/L, MgSO
47H
2O 0.1～1g/L, tween-80 0.1～5g/L, initial pH 6～9;
Culture condition:, cultivate 12～36h under 100～200r/min condition at 20～40 ℃;
(3) conversion and separation coupling technology: add Viscotrol C 20～30g/L behind strain culturing 12～36h, add macroporous adsorbent resin 60～100g/L, pH7.5, continues to transform 48～60h again by 20～40 ℃ under the condition of 100～200r/min.
2. method according to claim 1 is characterized in that big pore adsorption resin is the AB-8 resin, and this resin absorption converted product is with the toxicity of reduction high density product to yeast cell, and then raising output.
3. method according to claim 1 is characterized in that can reusing after the used resin regeneration.
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| CN2007100240490A CN101096692B (en) | 2007-07-12 | 2007-07-12 | Method for preparing gamma-decalactone and improving output by biotransformation and separated coupling |
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| CN2007100240490A CN101096692B (en) | 2007-07-12 | 2007-07-12 | Method for preparing gamma-decalactone and improving output by biotransformation and separated coupling |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102080109A (en) * | 2009-11-27 | 2011-06-01 | 爱普香料集团股份有限公司 | Method for preparing natural chiral gama-decalactone by using two-liquid-phase extraction bioanalysis method |
| CN107287253A (en) * | 2017-06-28 | 2017-10-24 | 岭南师范学院 | The method that immobilized cell produces gamma aminobutyric acid with D101 resins queen post |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0997533A1 (en) * | 1998-10-24 | 2000-05-03 | Haarmann & Reimer Gmbh | Process for the production of gamma-decalactone |
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2007
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102080109A (en) * | 2009-11-27 | 2011-06-01 | 爱普香料集团股份有限公司 | Method for preparing natural chiral gama-decalactone by using two-liquid-phase extraction bioanalysis method |
| CN102080109B (en) * | 2009-11-27 | 2014-03-12 | 爱普香料集团股份有限公司 | Method for preparing natural chiral gama-decalactone by using two-liquid-phase extraction bioanalysis method |
| CN107287253A (en) * | 2017-06-28 | 2017-10-24 | 岭南师范学院 | The method that immobilized cell produces gamma aminobutyric acid with D101 resins queen post |
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