CN101503712B - Method for preparing optically pure -2-octanol by immobilized microorganism - Google Patents
Method for preparing optically pure -2-octanol by immobilized microorganism Download PDFInfo
- Publication number
- CN101503712B CN101503712B CN2008101075955A CN200810107595A CN101503712B CN 101503712 B CN101503712 B CN 101503712B CN 2008101075955 A CN2008101075955 A CN 2008101075955A CN 200810107595 A CN200810107595 A CN 200810107595A CN 101503712 B CN101503712 B CN 101503712B
- Authority
- CN
- China
- Prior art keywords
- sec
- optical purity
- immobilized
- octyl alcohol
- adsorption resin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- 244000005700 microbiome Species 0.000 title claims abstract description 8
- 230000003287 optical effect Effects 0.000 claims abstract description 29
- 239000011347 resin Substances 0.000 claims abstract description 22
- 229920005989 resin Polymers 0.000 claims abstract description 22
- 238000001179 sorption measurement Methods 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 210000001822 immobilized cell Anatomy 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 239000007853 buffer solution Substances 0.000 claims abstract description 8
- 230000035484 reaction time Effects 0.000 claims abstract description 7
- 241000894006 Bacteria Species 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 20
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 15
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 11
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 10
- 239000008367 deionised water Substances 0.000 claims description 10
- 239000008103 glucose Substances 0.000 claims description 10
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 7
- 230000001580 bacterial effect Effects 0.000 claims description 6
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 claims description 5
- 239000001888 Peptone Substances 0.000 claims description 5
- 108010080698 Peptones Proteins 0.000 claims description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 5
- 229940041514 candida albicans extract Drugs 0.000 claims description 5
- 238000006555 catalytic reaction Methods 0.000 claims description 5
- 238000013016 damping Methods 0.000 claims description 5
- 230000008030 elimination Effects 0.000 claims description 5
- 238000003379 elimination reaction Methods 0.000 claims description 5
- 239000012530 fluid Substances 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 5
- 235000015097 nutrients Nutrition 0.000 claims description 5
- 235000019319 peptone Nutrition 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- 238000007669 thermal treatment Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000012138 yeast extract Substances 0.000 claims description 5
- 238000002203 pretreatment Methods 0.000 claims description 2
- 238000002791 soaking Methods 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 abstract description 7
- 239000000047 product Substances 0.000 abstract description 7
- 210000004027 cell Anatomy 0.000 abstract description 6
- 210000005253 yeast cell Anatomy 0.000 abstract description 6
- 108090000790 Enzymes Proteins 0.000 abstract description 5
- 102000004190 Enzymes Human genes 0.000 abstract description 5
- 239000005515 coenzyme Substances 0.000 abstract description 3
- 231100000331 toxic Toxicity 0.000 abstract description 3
- 230000002588 toxic effect Effects 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract 1
- 238000013048 microbiological method Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 235000008429 bread Nutrition 0.000 description 6
- 239000011259 mixed solution Substances 0.000 description 6
- 239000004973 liquid crystal related substance Substances 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000002024 ethyl acetate extract Substances 0.000 description 3
- 238000003810 ethyl acetate extraction Methods 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical group CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 101710157860 Oxydoreductase Proteins 0.000 description 1
- 241000235070 Saccharomyces Species 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000003225 biodiesel Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 229940081969 saccharomyces cerevisiae Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention discloses a method for preparing high-optical-purity -2-octanol by a microbiological method and a microorganism thereof. The immobilized cell synthesis method has the following advantages: 1. the immobilization process is simple, the immobilized yeast cells have certain antitoxicity in a reaction system, the catalytic effect is good, and the immobilized yeast cells can be repeatedly used. 2. The immobilized cell prepared by using the nonpolar macroporous adsorption resin as a carrier has the advantages of good elasticity, strong tolerance to temperature and pH value, high mechanical strength, stable enzyme activity and long half-life. 3. The reaction is carried out in the organic solvent/buffer solution two phases, so that the toxic action of the organic solvent on cells can be reduced, and the catalytic activity of the organic solvent is improved. 4. The immobilized yeast cell is used for preparing the optically pure -2-octanol in a catalytic manner, the process is simple, expensive coenzyme does not need to be added, the condition is mild, the reaction time is short, few byproducts are generated, the optical purity is as high as 90.25 percent of e.e., the subsequent treatment is simple, the product is easy to separate, and the environment is friendly.
Description
Technical field
Mikrobe prepares the method for optical purity (R)-sec-n-octyl alcohol, belongs to the technical field of the synthetic optical pure compound of mikrobe asymmetry catalysis prochirality compound.
Background technology
Sec-n-octyl alcohol is called secondary octanol again, often is used to Minute Organic Synthesis, can be used for production chirality chemical material and spices.(R)-sec-n-octyl alcohol is the important chiral material of preparation high-performance liquid crystal and liquid crystal device, can increase substantially the liquid crystal quality, makes low-grade liquid crystal (no chirality) become high-grade liquid crystal (chirality).It also is the important intermediate of synthetic many optical activity medicines and agricultural chemicals simultaneously.The method for preparing the optical purity sec-n-octyl alcohol known today mainly contains three approach: (1) chemical method.Normally utilize chemical method to prepare the optical purity sec-n-octyl alcohol, existence needs to add expensive and has toxic chiral catalyst (vauqueline), complicated operation; It is bigger to split difficulty, and yield is low, causes not enough [Ma Hongyi such as environmental pollution; Henan chemical industry .2004,8:15-16; Chi Shujuan etc., Liaoning chemical industry .2007,19 (4): 196-198].(2) enzyme process.Utilize lipase-catalyzed resolution of racemates sec-n-octyl alcohol to prepare the optical purity sec-n-octyl alcohol, but the not reproducible use of catalyzer, by product is many; Yield is low, and subsequent disposal is complicated, and product is not easily separated; In practical application, receive certain restriction [Gao Hongjuan etc., fine chemistry industry .2008,25 (4): 338-341; Shi Xianai etc., South China Science & Engineering University's journal (natural science edition) .2006,34 (12): 30-34; Single sky etc., catalysis journal .2008,29 (4): 403-408; Zhu Jie etc., catalysis journal .1998,19 (3): 255-259; Dai Dazhang etc., SCI .2007,28 (12): 2307-2310; Jiang Juan etc., chemical industry progress .2006,25 (8): 947-962].(3) cell method.Because microorganism cells contains complete enzyme system, for example contain abundant oxydo-reductase system in the yeast cell, can realize the reducing/regenerating of coenzyme; Do not need to add in addition expensive cofactors, several no coupling products, yield improves greatly; Simplified subsequent processes, but the not reproducible use of cell, product separates still too complicated [Li Yongning etc.; Medicine biotechnology .2006,13 (6): 446-450; Yang Zhonghua etc., chemical industry journal .2004,55 (8): 1301-1305; Hu Jian etc., chemical industry journal .2006,57 (10): 2383-2387].
Summary of the invention
The method that the purpose of this invention is to provide a kind of immobilized microorganism catalytic preparation optical purity (R)-sec-n-octyl alcohol.
The present invention realizes through following mode:
A kind of immobilized microorganism prepares the method for optical purity (R)-sec-n-octyl alcohol, and its characteristic may further comprise the steps:
(1), the nonpolar macroporous adsorption resin pre-treatment: with nonpolar macroporous adsorption resin with washed with de-ionized water after with containing the NaOH solution soaking 24-48h of 0.5-5.0%, with washed with de-ionized water to neutral, oven dry;
(2), bread yeast immobilization: routine is cultivated bread yeast DX213 Saccharomyces cerevisiaeDX213 CCTCC NO:M 207082, gets bacterium liquid, and nonpolar macroporous adsorption resin is soaked in the bacterium liquid; 25-35 ℃ of bacterium liquid temp, the pH value is 6.0-8.0, shakes a bottle revolution 100-400rpm; Fixing bacterial classification 24-48h, elimination bacterium liquid, and wash with saline water; With immobilized cell thermal treatment 10-60min, make nonpolar macroporous adsorption resin immobilization bread yeast;
(3), immobilization bread yeast catalysis methyln-hexyl ketone prepares optical purity (R)-sec-n-octyl alcohol: immobilized cell is dissolved in the Tris-HCl damping fluid of 0.1mol/L, making its concentration is 0.2-0.5g/mL, pours among organic solvent tetrahydrofuran, methylene dichloride, normal hexane, toluene, hexane or sherwood oil a kind of; Making its organic solvent volume ratio is 5/30-35/0; Divide 2-5 batch to add methyln-hexyl ketone then, make its mass concentration 24-60mmoL/L, with glucose, sucrose, 1; A kind of in 2-Ucar 35, methyl alcohol or the Hydrocerol A is cosubstrate; Addition is 0.5-3.0g, and pH value of buffer solution is 3.0-10.0 in the reaction system, temperature of reaction 26-36 ℃; Reaction times 2-72h gets optical purity (R)-sec-n-octyl alcohol.
The conventional substratum of cultivating consists of the contained component of every L nutrient solution in g: glucose 20.0-60.0, yeast extract paste 1.0-10.0, peptone 1.0-10.0, K
2HPO
40.2-4.0, KH
2PO
40.5-5.0, MgSO
40.02-2.0.
With respect to traditional chemical method, enzyme process and cell method, immobilized cell synthesis method of the present invention has following advantage: 1, immobilization technology is simple, and fixed yeast cell has certain poison resistance in reaction system, and excellent catalytic effect is reusable.2, nonpolar macroporous adsorption resin is the immobilized cell of preparing carriers, and good springiness is strong to the tolerance of temperature, pH value, and physical strength is high, and enzyme is lived stable, long half time.3, react in mutually in organic solvent two, can reduce the toxic action of organic solvent pair cell, improve its catalytic activity.4, fixed yeast cell catalytic preparation optical purity (R)-sec-n-octyl alcohol, technology is simple, need not add expensive coenzyme, mild condition, the reaction times is short, several no coupling products, optical purity is up to 90%e.e., and subsequent disposal is simple, and product is easily separated, environmental friendliness.
Embodiment
Below in conjunction with embodiment the present invention is further specified:
The present invention is to be in the organic solvent two-phase system of 5/30-35/0 in volume ratio, initial substrate methyln-hexyl ketone 24-60mmoL/L, and the cosubstrate that adds 0.5-3.0g reacts 2-72h in 26-36 ℃; Product obtains optical purity (R)-sec-n-octyl alcohol after separation and purification.Bread yeast DX213 (Saccharomycescerevisiae DX213) bacterial classification is at applicant's application " working method of a kind of bread yeast and catalyzed production biodiesel thereof " patent (application number: 200710035224.6; The applying date: in the time of 2007.6.27); Chinese Wuhan Wuhan University Chinese typical culture collection center, deposit number CCTCC NO:M 207082 have been deposited in on June 18th, 2007.
Embodiment 1
D-101 type nonpolar macroporous adsorption resin is repeatedly soaked 48h with 0.5% NaOH in the back with washed with de-ionized water, to neutral, dry with washed with de-ionized water;
In substratum, insert bread yeast and carry out routine cultivation, substratum consist of the contained component of every L nutrient solution in g: glucose 20.0, yeast extract paste 1.0, peptone 5.0, K
2HPO
41.0, KH
2PO
41.0, MgSO
40.2, make bacterium liquid, D-101 type nonpolar macroporous adsorption resin is soaked in the bacterium liquid; 30 ℃ of bacterium liquid temps, the pH value is 6.5, shakes a bottle revolution 150rpm; Fixing bacterial classification 28h, elimination bacterium liquid, and wash with saline water; With immobilized cell thermal treatment 15min, make nonpolar macroporous adsorption resin immobilization bread leaven matricyte.
D-101 type nonpolar macroporous adsorption resin immobilization bread leaven matricyte is dissolved in the Tris-HCl damping fluid of 0.1mol/L, and making its quality is 0.3g/mL, pours toluene into, and the volume ratio that makes toluene and buffered soln is 15/20.Then, divide two batches to add methyln-hexyl ketone in the mixed solution of toluene/buffered soln, make its mass concentration 30mmol/L, cosubstrate glucose addition is 0.7g.PH value of buffer solution is 7.0 in the reaction system, 28 ℃ of temperature of reaction, reaction times 38h.Separating catalyst, standing demix, the upper strata is for containing the mixed solution of optical purity (R)-sec-n-octyl alcohol; Use the equal-volume ethyl acetate extraction, add anhydrous magnesium sulfate in acetic acid ethyl acetate extract, static spending the night; Remove residual water-content, reclaim the residual acetic acid ethyl ester, get optical purity (R)-sec-n-octyl alcohol.The productive rate of optical purity (R)-sec-n-octyl alcohol is 16.56%, and optical purity is 30.57% (liquid chromatography).
Embodiment 2
H103 type nonpolar macroporous adsorption resin is repeatedly soaked 30h with 2.0% NaOH in the back with washed with de-ionized water, and washed with de-ionized water is dried to neutral;
In substratum, insert bread yeast and carry out routine cultivation, substratum consist of the contained component of every L nutrient solution in g: glucose 60.0, yeast extract paste 8.0, peptone 1.0, K
2HPO
42.0, KH
2PO
42.0, MgSO
40.5, make bacterium liquid, H103 type nonpolar macroporous adsorption resin is soaked in the bacterium liquid; 28 ℃ of bacterium liquid temps, the pH value is 7.0, shakes a bottle revolution 200rpm; Fixing bacterial classification 40h, elimination bacterium liquid, and wash with saline water; With immobilized cell thermal treatment 60min, make nonpolar macroporous adsorption resin immobilization bread leaven matricyte.
H103 type nonpolar macroporous adsorption resin immobilization bread leaven matricyte is dissolved in the Tris-HCl damping fluid of 0.1mol/L, and making its quality is 0.3g/mL, pours sherwood oil into, and making sherwood oil and volume of buffer solution ratio is 25/20.Then, time interpolation methyln-hexyl ketone makes its mass concentration 50mmol/L in the mixed solution of sherwood oil/buffered soln in four batches.Cosubstrate glucose addition is 2.0g.PH value of buffer solution is 6.5 in the reaction system, 35 ℃ of temperature of reaction, reaction times 42h.Separating catalyst, standing demix, the upper strata is for containing the mixed solution of optical purity (R)-sec-n-octyl alcohol; Use the equal-volume ethyl acetate extraction, add anhydrous magnesium sulfate in acetic acid ethyl acetate extract, static spending the night; Remove residual water-content, reclaim the residual acetic acid ethyl ester, get optical purity (R)-sec-n-octyl alcohol.The productive rate 86.46% of optical purity (R)-sec-n-octyl alcohol, optical purity are 90.25% (liquid chromatography).
Embodiment 3
HPD-300 type nonpolar macroporous adsorption resin is repeatedly soaked 24h with 4.0% NaOH in the back with washed with de-ionized water, and washed with de-ionized water is dried to neutral;
In substratum, insert bread yeast and carry out routine cultivation, substratum consist of the contained component of every L nutrient solution in g: glucose 30.0, yeast extract paste 4.0, peptone 6.0, K
2HPO
41.0, KH
2PO
42.0, MgSO
40.5, make bacterium liquid, HPD-300 type nonpolar macroporous adsorption resin is soaked in the bacterium liquid; 28 ℃ of bacterium liquid temps, the pH value is 7.0, shakes a bottle revolution 180rpm; Fixing bacterial classification 48h, elimination bacterium liquid, and wash with saline water; With immobilized cell thermal treatment 55min, make nonpolar macroporous adsorption resin immobilization bread leaven matricyte.
HPD-300 type macroporous adsorbent resin immobilization bread leaven matricyte is dissolved in the Tris-HCl damping fluid of 0.1mol/L, and making its quality is 0.3g/mL, pours methylene dichloride into, and making methylene dichloride and volume of buffer solution ratio is 30/8.Three batches are added methyln-hexyl ketone in the mixed solution of methylene dichloride/buffered soln then, make its mass concentration 25mmol/L, and cosubstrate glucose addition is 2.0g.PH value of buffer solution is 8.0 in the reaction system, 27 ℃ of temperature of reaction, reaction times 45h.Separating catalyst, standing demix, the upper strata is for containing the mixed solution of optical purity (R)-sec-n-octyl alcohol; Use the equal-volume ethyl acetate extraction, add anhydrous magnesium sulfate in acetic acid ethyl acetate extract, static spending the night; Remove residual water-content, reclaim the residual acetic acid ethyl ester, get (R)-sec-n-octyl alcohol.(R)-and the productive rate 86.46% of sec-n-octyl alcohol, optical purity is 90.25% (liquid chromatography).
Claims (2)
1. an immobilized microorganism prepares the method for optical purity (R)-sec-n-octyl alcohol, and its characteristic may further comprise the steps:
(1), the nonpolar macroporous adsorption resin pre-treatment: with nonpolar macroporous adsorption resin with washed with de-ionized water after with containing the NaOH solution soaking 24-48h of 0.5-5.0%, with washed with de-ionized water to neutral, oven dry;
(2), bread yeast immobilization: routine is cultivated bread yeast (Saccharomyces cerevisiae) DX213 CCTCC NO:M 207082, gets bacterium liquid, and nonpolar macroporous adsorption resin is soaked in the bacterium liquid; 25-35 ℃ of bacterium liquid temp, the pH value is 6.0-8.0, shakes a bottle revolution 100-400rpm; Fixing bacterial classification 24-48h, elimination bacterium liquid, and wash with saline water; With immobilized cell thermal treatment 10-60min, make nonpolar macroporous adsorption resin immobilization bread yeast;
(3), immobilization bread yeast catalysis methyln-hexyl ketone prepares optical purity (R)-sec-n-octyl alcohol: immobilized cell is dissolved in the Tris-HCl damping fluid of 0.1mol/L; Making its concentration is 0.2-0.5g/mL; Pour among organic solvent dichloromethane or sherwood oil a kind of, making the organic solvent volume ratio is 25/20 or 30/8; Dividing 2-5 batch of interpolation methyln-hexyl ketone to make its mass concentration then is 20-80mmoL/L, and cosubstrate is a glucose, and addition is 0.5-3.0g; PH value of buffer solution is 3.0-10.0 in the reaction system; Temperature of reaction 26-36 ℃, reaction times 2-72h gets optical purity (R)-sec-n-octyl alcohol.
2. a kind of immobilized microorganism according to claim 1 prepares the method for optical purity (R)-sec-n-octyl alcohol; It is characterized in that the conventional substratum of cultivating consists of the contained component of every L nutrient solution in g: glucose 20.0-60.0; Yeast extract paste 1.0-10.0, peptone 1.0-10.0, K
2HPO
40.2-4.0, KH
2PO
40.5-5.0, MgSO
40.02-2.0.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008101075955A CN101503712B (en) | 2008-12-26 | 2008-12-26 | Method for preparing optically pure -2-octanol by immobilized microorganism |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2008101075955A CN101503712B (en) | 2008-12-26 | 2008-12-26 | Method for preparing optically pure -2-octanol by immobilized microorganism |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101503712A CN101503712A (en) | 2009-08-12 |
| CN101503712B true CN101503712B (en) | 2012-05-23 |
Family
ID=40976087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2008101075955A Expired - Fee Related CN101503712B (en) | 2008-12-26 | 2008-12-26 | Method for preparing optically pure -2-octanol by immobilized microorganism |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101503712B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104342464A (en) * | 2014-10-30 | 2015-02-11 | 青岛科技大学 | Method for producing chiral phenyl methanol employing catalysis of tarlaromyces flavus |
| CN104388490A (en) * | 2014-10-30 | 2015-03-04 | 青岛科技大学 | Method for producing chiral pyrazinyl ethanol by biological catalysis |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5112750A (en) * | 1985-06-25 | 1992-05-12 | Asama Chemical Co., Ltd. | Immobilized cells and culture method utilizing the same |
| US6451587B1 (en) * | 1999-09-29 | 2002-09-17 | Pfizer Inc. | Microbial asymmetric reduction of 2-chloro-1-[-6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-3-yl]-ethanone |
| CN1597970A (en) * | 2004-07-19 | 2005-03-23 | 江南大学 | Process for preparation optical pure (R)-2- octanol by microorganism and its special microorganism |
| CN101230320A (en) * | 2007-06-27 | 2008-07-30 | 湘潭大学 | Baker's yeast and catalytic production method of biodiesel thereof |
| CN101314787A (en) * | 2008-06-24 | 2008-12-03 | 江苏华荣生物科技有限公司 | Method for preparing optical activity chiral secondary alcohol by using rhodotorula reductase preparation |
-
2008
- 2008-12-26 CN CN2008101075955A patent/CN101503712B/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5112750A (en) * | 1985-06-25 | 1992-05-12 | Asama Chemical Co., Ltd. | Immobilized cells and culture method utilizing the same |
| US6451587B1 (en) * | 1999-09-29 | 2002-09-17 | Pfizer Inc. | Microbial asymmetric reduction of 2-chloro-1-[-6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-3-yl]-ethanone |
| CN1597970A (en) * | 2004-07-19 | 2005-03-23 | 江南大学 | Process for preparation optical pure (R)-2- octanol by microorganism and its special microorganism |
| CN101230320A (en) * | 2007-06-27 | 2008-07-30 | 湘潭大学 | Baker's yeast and catalytic production method of biodiesel thereof |
| CN101314787A (en) * | 2008-06-24 | 2008-12-03 | 江苏华荣生物科技有限公司 | Method for preparing optical activity chiral secondary alcohol by using rhodotorula reductase preparation |
Non-Patent Citations (3)
| Title |
|---|
| 李泳宁等.非水相固定化酵母催化(S)-2-辛醇的不对称合成.<<药物生物技术>>.2006,第13卷(第6期),第446-450页. * |
| 杨忠华等.酵母催化2-辛酮不对称还原为2-辛醇.《化工学报》.2004,第55卷(第8期),1301-1305. * |
| 黄和等.面包酵母催化羟基不对称还原合成手性醇的研究.《生物加工过程》.2004,第2卷(第2期),第52-55页. * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101503712A (en) | 2009-08-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO793101L (en) | PROCEDURE FOR ENZYM BACKGROUND. | |
| CN107746871B (en) | Method for preparing rare ginsenoside by biotransformation of ginsenoside with schizophyllum commune | |
| CN101503712B (en) | Method for preparing optically pure -2-octanol by immobilized microorganism | |
| CN103725719A (en) | Methods of producing carboxylic acids and/or alcohols | |
| CN108611380A (en) | A kind of method of selectivity synthesis 2,5- dihydroxymethyl furans | |
| CN103805657A (en) | Method of synthesizing alpha-arbutin by catalyzing immobilized hydroquinone by free cells | |
| CN101503711B (en) | Method for preparing optical pure (R)-2-octanol by immobilized cell | |
| CN108456665A (en) | A method of promoting gluconobacter oxydans synthesis sorbitol dehydrogenase and coenzyme pyrroloquinoline quinone | |
| CN101709322B (en) | Method for synthesizing betulic acid by carrying out biocatalysis on betulin | |
| CN110129399B (en) | Method for promoting HAU-M1 photosynthetic bacteria to efficiently produce hydrogen by utilizing chlorella biomass | |
| CN101481725B (en) | Method for preparing ginseng saponin F2 by enzymatic hydrolysis of ginseng saponin Rb1 | |
| CN101302552B (en) | Method for preparing (R)-2-chlorin-1-(3-chlorphenyl) ethanol by microorganism catalysis | |
| CN101210258A (en) | Method for preparing (R)-3-hydroxyethyl butyrate by microorganism conversion | |
| CN101475932A (en) | Method for immobilizing cell for producing Clostridium acetobutylicum | |
| CN102071231B (en) | Method for preparing S-(+)-3-hydroxy tetrahydrofuran through microbial conversion | |
| Křen et al. | Glycosylation of ergot alkaloids by free and immobilized cells of Claviceps purpurea | |
| CN103484505B (en) | Method for generating resveratrol by converting glucose by using intracellular enzyme of alternaria microorganism | |
| CN113215203B (en) | Method for producing ethanol by co-fermentation saccharomycetes through expansion culture and fermentation | |
| CN113122522B (en) | Method for promoting biological fermentation to produce cellulase | |
| CN102952760B (en) | Rhodococcus erythropolis capable of converting quininone into (S)-3-quinuclidinol and conversion method | |
| CN114807247B (en) | Application of candida ludwigii in catalyzing citral to generate dextro citronellal and method for preparing levo isopulegol | |
| CN102994403A (en) | Rhodotorula glutinis and application of Rhodotorula glutinis in preparation of (R)-2-hydroxy-4- phenyl ethyl butyrate through asymmetric catalysis | |
| CN111534472B (en) | Bacillus aryabhattai WZZ10 and application thereof in chiral resolution of 2-tetrahydrofurfuryl acid | |
| CN110904160B (en) | Fermentation method for increasing beta-phenethyl alcohol unit yield | |
| CN103436455B (en) | S. cerevisiae strain for producing citicoline through bioconversion and application of S. cerevisiae strain |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20120523 Termination date: 20121226 |