CA2000721A1 - Procede de production de l-phenyl acetyl carbinol (pac), masse cellulaire immobilisee utilisee dans le processus et methode de preparation de ladite masse cellulaire - Google Patents
Procede de production de l-phenyl acetyl carbinol (pac), masse cellulaire immobilisee utilisee dans le processus et methode de preparation de ladite masse cellulaireInfo
- Publication number
- CA2000721A1 CA2000721A1 CA 2000721 CA2000721A CA2000721A1 CA 2000721 A1 CA2000721 A1 CA 2000721A1 CA 2000721 CA2000721 CA 2000721 CA 2000721 A CA2000721 A CA 2000721A CA 2000721 A1 CA2000721 A1 CA 2000721A1
- Authority
- CA
- Canada
- Prior art keywords
- cells
- pac
- cell mass
- cell
- polyazetidine
- 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.)
- Abandoned
Links
- 210000004027 cell Anatomy 0.000 title claims abstract description 129
- 238000000034 method Methods 0.000 title claims abstract description 73
- 230000008569 process Effects 0.000 title claims abstract description 56
- ZBFFNPODXBJBPW-VIFPVBQESA-N (R)-phenylacetylcarbinol Chemical compound CC(=O)[C@H](O)C1=CC=CC=C1 ZBFFNPODXBJBPW-VIFPVBQESA-N 0.000 title claims abstract description 31
- 210000001822 immobilized cell Anatomy 0.000 title claims abstract description 28
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 99
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 50
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims abstract description 39
- 238000004519 manufacturing process Methods 0.000 claims abstract description 39
- 239000006184 cosolvent Substances 0.000 claims abstract description 35
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims abstract description 17
- 108010011939 Pyruvate Decarboxylase Proteins 0.000 claims abstract description 16
- 210000002421 cell wall Anatomy 0.000 claims abstract description 12
- 230000005764 inhibitory process Effects 0.000 claims abstract description 12
- 239000012736 aqueous medium Substances 0.000 claims abstract description 11
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 9
- 239000000376 reactant Substances 0.000 claims abstract description 7
- 230000035699 permeability Effects 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims description 38
- 230000015572 biosynthetic process Effects 0.000 claims description 17
- 238000005755 formation reaction Methods 0.000 claims description 14
- 239000002245 particle Substances 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 9
- 239000002202 Polyethylene glycol Substances 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 210000005253 yeast cell Anatomy 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229920005862 polyol Polymers 0.000 claims description 5
- 150000003077 polyols Chemical group 0.000 claims description 5
- 230000000717 retained effect Effects 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 2
- 238000005549 size reduction Methods 0.000 claims description 2
- 108090000489 Carboxy-Lyases Proteins 0.000 claims 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 abstract description 11
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 abstract description 6
- 229960002179 ephedrine Drugs 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 4
- ZBFFNPODXBJBPW-UHFFFAOYSA-N 1-hydroxy-1-phenylpropan-2-one Chemical compound CC(=O)C(O)C1=CC=CC=C1 ZBFFNPODXBJBPW-UHFFFAOYSA-N 0.000 description 94
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 33
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 238000000855 fermentation Methods 0.000 description 19
- 230000004151 fermentation Effects 0.000 description 19
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 17
- 239000012429 reaction media Substances 0.000 description 17
- 229940076788 pyruvate Drugs 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 235000019445 benzyl alcohol Nutrition 0.000 description 11
- 229960004217 benzyl alcohol Drugs 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 244000005700 microbiome Species 0.000 description 9
- 230000009466 transformation Effects 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 238000004132 cross linking Methods 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000011324 bead Substances 0.000 description 6
- 229960004756 ethanol Drugs 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 241001043481 Debaryomyces subglobosus Species 0.000 description 4
- 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 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 4
- -1 alkali metal salt Chemical class 0.000 description 4
- 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 4
- 239000006227 byproduct Substances 0.000 description 4
- 229960001031 glucose Drugs 0.000 description 4
- 235000001727 glucose Nutrition 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920002523 polyethylene Glycol 1000 Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005273 aeration Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000003306 harvesting Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000133 nasal decongestant Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229960003908 pseudoephedrine Drugs 0.000 description 2
- 229940107700 pyruvic acid Drugs 0.000 description 2
- 239000011535 reaction buffer Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
- 229960002363 thiamine pyrophosphate Drugs 0.000 description 2
- 235000008170 thiamine pyrophosphate Nutrition 0.000 description 2
- 239000011678 thiamine pyrophosphate Substances 0.000 description 2
- YXVCLPJQTZXJLH-UHFFFAOYSA-N thiamine(1+) diphosphate chloride Chemical compound [Cl-].CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N YXVCLPJQTZXJLH-UHFFFAOYSA-N 0.000 description 2
- NUKQEEMKQGMUQH-UHFFFAOYSA-N 1-methyl-1-nitrosoguanidine Chemical compound O=NN(C)C(N)=N NUKQEEMKQGMUQH-UHFFFAOYSA-N 0.000 description 1
- 102000007698 Alcohol dehydrogenase Human genes 0.000 description 1
- 108010021809 Alcohol dehydrogenase Proteins 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 101150096672 CEL1 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 210000000712 G cell Anatomy 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 1
- 229920002562 Polyethylene Glycol 3350 Polymers 0.000 description 1
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 1
- 229920002594 Polyethylene Glycol 8000 Polymers 0.000 description 1
- 101150094640 Siae gene Proteins 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 239000012431 aqueous reaction media Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000002844 continuous effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- OYFJQPXVCSSHAI-QFPUQLAESA-N enalapril maleate Chemical compound OC(=O)\C=C/C(O)=O.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 OYFJQPXVCSSHAI-QFPUQLAESA-N 0.000 description 1
- 229940124582 fever medication Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011221 initial treatment Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000012092 media component Substances 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000000711 polarimetry Methods 0.000 description 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
- C12P7/26—Ketones
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26062288A | 1988-10-21 | 1988-10-21 | |
| US260,622 | 1988-10-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2000721A1 true CA2000721A1 (fr) | 1990-04-21 |
Family
ID=22989911
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2000721 Abandoned CA2000721A1 (fr) | 1988-10-21 | 1989-10-16 | Procede de production de l-phenyl acetyl carbinol (pac), masse cellulaire immobilisee utilisee dans le processus et methode de preparation de ladite masse cellulaire |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0439527A4 (fr) |
| JP (1) | JPH04502104A (fr) |
| AU (1) | AU4501989A (fr) |
| CA (1) | CA2000721A1 (fr) |
| WO (1) | WO1990004639A1 (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5079145A (en) * | 1988-10-21 | 1992-01-07 | Synergen Associates, Inc. | Process for preparing microorganisms used for making phenyl acetyl carlinol (pac) |
| AUPP388298A0 (en) | 1998-06-03 | 1998-06-25 | Polychip Pharmaceuticals Pty Ltd | Precursers of pharmaceutical compounds |
| AUPQ462599A0 (en) * | 1999-12-13 | 2000-01-13 | Polychip Pharmaceuticals Pty Ltd | Yeast-based process for production of l-pac |
| DE10032058A1 (de) * | 2000-07-05 | 2002-01-17 | Basf Ag | Mikrobielle Produktion von R-Phenylacetylcarbinol durch biologische Umwandlung von Benzaldehyd durch filamentöse Pilze |
| DE10142574A1 (de) | 2001-09-01 | 2003-03-20 | Basf Ag | Verfahren zur Herstellung von R-Phenylacetylcarbinol durch ein enzymatisches verfahren in einem Zweiphasensystem |
| WO2007077141A1 (fr) * | 2006-01-06 | 2007-07-12 | Basf Aktiengesellschaft | Procede de production de phenylacetylcarbinol substitue |
| KR20140127159A (ko) * | 2013-04-24 | 2014-11-03 | 후지필름 가부시키가이샤 | 여과 필터, 여과 방법, 셀룰로오스 아실레이트 필름 및 그 제조 방법 |
| DE102017210944B4 (de) | 2017-06-28 | 2019-05-23 | Technische Universität Dresden | Alkoholdehydrogenasen und Verfahren zur stereoselektiven Reduktion von Carbonylverbindungen |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3338796A (en) * | 1966-10-13 | 1967-08-29 | Merck & Co Inc | Converting veratraldehyde to l(-)3, 4-dimethoxyphenylacetyl carbinol |
| CH564602A5 (de) * | 1973-01-10 | 1975-07-31 | Battelle Memorial Institute | Verfahren und Vorrichtung zur ständigen Steuerung des Ablaufs einer Enzym-Reaktion |
| US4436813A (en) * | 1982-03-16 | 1984-03-13 | Purification Engineering, Inc. | Immobilized microbial cell composition for making L-aspartic acid |
| US4732851A (en) * | 1982-03-16 | 1988-03-22 | Purification Engineering, Inc. | Immobilization of cells with a polyazetidine prepolymer |
| US4728611A (en) * | 1983-07-29 | 1988-03-01 | Purification Engineering, Inc. | Production of phenylalanine with immobilized cells |
-
1989
- 1989-10-13 WO PCT/US1989/004421 patent/WO1990004639A1/fr not_active Ceased
- 1989-10-13 JP JP1511245A patent/JPH04502104A/ja active Pending
- 1989-10-13 AU AU45019/89A patent/AU4501989A/en not_active Abandoned
- 1989-10-13 EP EP19890912199 patent/EP0439527A4/en not_active Withdrawn
- 1989-10-16 CA CA 2000721 patent/CA2000721A1/fr not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP0439527A1 (fr) | 1991-08-07 |
| EP0439527A4 (en) | 1991-11-21 |
| AU4501989A (en) | 1990-05-14 |
| JPH04502104A (ja) | 1992-04-16 |
| WO1990004639A1 (fr) | 1990-05-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4368268A (en) | Direct fermentation of D-xylose to ethanol by a xylose-fermenting yeast mutant | |
| Wada et al. | Continuous production of ethanol using immobilized growing yeast cells | |
| Wada et al. | Continuous production of ethanol in high concentration using immobilized growing yeast cells | |
| Shukla et al. | L-Phenylacetylcarbinol (L-PAC): biosynthesis and industrial applications | |
| US10301655B2 (en) | Method for producing acetoin | |
| EP0066396B1 (fr) | Fermentation directe de d-xylose en éthanol par une levure mutée capable de fermenter le xylose | |
| CA2732204A1 (fr) | Procede de production | |
| CA2000721A1 (fr) | Procede de production de l-phenyl acetyl carbinol (pac), masse cellulaire immobilisee utilisee dans le processus et methode de preparation de ladite masse cellulaire | |
| JP5804719B2 (ja) | （ｓ）−１，１，１−トリフルオロ−２−プロパノールの工業的な製造方法 | |
| CA1210716A (fr) | Production continue d'ethanol par des levures mutantes | |
| Ueng et al. | D-Xylulose fermentation in yeasts | |
| Blandino et al. | Comparative study of alcohol dehydrogenase activity in flor yeast extracts | |
| Linko et al. | Alcoholic fermentation of D-xylose by immobilized Pichia stipitis yeast | |
| Sakai et al. | Formaldehyde production by cells of a mutant of Candida boidinii S2 grown in methanol-limited chemostat culture | |
| US4720457A (en) | Selective production of ethyl acetate and acetaldehyde by microorganisms | |
| Gunasekaran et al. | High ethanol productivity from lactose by immobilized cells of Kluyveromyces fragilis and Zymomonas mobilis | |
| Suihko et al. | Pentose fermentation by yeasts | |
| FR2461753A1 (fr) | Procede de preparation d'une cephalosporine par fermentation et micro-organisme destine a la mise en oeuvre de ce procede | |
| KR0153091B1 (ko) | 산소분압의 조절을 이용한 자일리톨의 생물공학적 제조방법 | |
| US5312742A (en) | Process for making L-phenyl acetyl carbinol (PAC), microorganisms for use in the process, and a method of preparing the microorganisms | |
| Rohner et al. | Process for the stereoselective biotransformation of acetoacetic acid esters using yeasts | |
| KR20150076048A (ko) | 부산물을 이용한 에리스리톨 제조 방법, 에리스리톨 생산성이 우수한 모닐리엘라 폴리니스 변이 균주 및 이의 이용 | |
| Azari et al. | Evaluation of immobilized cytochrome P-448 from Saccharomyces cerevisiae using permeabilized whole cell, microsomal fraction and highly purified reconstituted forms, with benzopyrene-3-monooxygenase activity | |
| Eguchi et al. | NADP+ reduction by a methanogen using HCOOH or H2 as electron donor | |
| EP0542300A2 (fr) | Méthode de préparation de (S)-1-phényl-1,3-propanediol ou ses dérivés |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |