DE2733202A1 - Verfahren zur herstellung der d(-)-3-hydroxybuttersaeure - Google Patents
Verfahren zur herstellung der d(-)-3-hydroxybuttersaeureInfo
- Publication number
- DE2733202A1 DE2733202A1 DE19772733202 DE2733202A DE2733202A1 DE 2733202 A1 DE2733202 A1 DE 2733202A1 DE 19772733202 DE19772733202 DE 19772733202 DE 2733202 A DE2733202 A DE 2733202A DE 2733202 A1 DE2733202 A1 DE 2733202A1
- Authority
- DE
- Germany
- Prior art keywords
- hydroxybutyric acid
- acid
- cbs
- atcc
- mutant
- 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.)
- Withdrawn
Links
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- 230000008569 process Effects 0.000 title claims description 12
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- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229960001127 colistin sulfate Drugs 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- XJRPTMORGOIMMI-UHFFFAOYSA-N ethyl 2-amino-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound CCOC(=O)C=1SC(N)=NC=1C(F)(F)F XJRPTMORGOIMMI-UHFFFAOYSA-N 0.000 description 1
- KWWOQRSLYPHAMK-UHFFFAOYSA-N ethyl 2-hydroxybutanoate Chemical compound CCOC(=O)C(O)CC KWWOQRSLYPHAMK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- -1 fructose or glycerin Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002314 glycerols Chemical class 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 150000001457 metallic cations Chemical class 0.000 description 1
- OGXRXFRHDCIXDS-UHFFFAOYSA-N methanol;propane-1,2,3-triol Chemical compound OC.OCC(O)CO OGXRXFRHDCIXDS-UHFFFAOYSA-N 0.000 description 1
- CEQFOVLGLXCDCX-WUKNDPDISA-N methyl red Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=CC=C1C(O)=O CEQFOVLGLXCDCX-WUKNDPDISA-N 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- ZESIAEVDVPWEKB-ORCFLVBFSA-N n-[(2s)-4-amino-1-[[(2s,3r)-1-[[(2s)-4-amino-1-oxo-1-[[(3s,6s,9s,12s,15r,18s,21s)-6,9,18-tris(2-aminoethyl)-3-[(1r)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-h Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.CC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O.CCC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@H]([C@@H](C)O)CN[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O ZESIAEVDVPWEKB-ORCFLVBFSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
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- 229940056360 penicillin g Drugs 0.000 description 1
- 229950009506 penicillinase Drugs 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- 230000004260 plant-type cell wall biogenesis Effects 0.000 description 1
- 229920000024 polymyxin B Polymers 0.000 description 1
- 229960005266 polymyxin b Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000001523 saccharolytic effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- NBPUSGBJDWCHKC-UHFFFAOYSA-M sodium 3-hydroxybutyrate Chemical compound [Na+].CC(O)CC([O-])=O NBPUSGBJDWCHKC-UHFFFAOYSA-M 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 239000012137 tryptone Substances 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
-
- 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
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/42—Hydroxy-carboxylic acids
-
- 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
- C12P7/62—Carboxylic acid esters
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/829—Alcaligenes
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/831—Azotobacter
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/8215—Microorganisms
- Y10S435/822—Microorganisms using bacteria or actinomycetales
- Y10S435/832—Bacillus
- Y10S435/837—Bacillus megaterium
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (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)
- Fodder In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH995776A CH621148A5 (en) | 1976-08-04 | 1976-08-04 | Process for obtaining bacterial strains and their use for the preparation of an optically active carboxylic acid |
| CH1001076A CH620706A5 (en) | 1976-08-05 | 1976-08-05 | Process for the preparation of esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2733202A1 true DE2733202A1 (de) | 1978-02-09 |
Family
ID=25705617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772733202 Withdrawn DE2733202A1 (de) | 1976-08-04 | 1977-07-22 | Verfahren zur herstellung der d(-)-3-hydroxybuttersaeure |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4211846A (enExample) |
| JP (1) | JPS5318794A (enExample) |
| AU (1) | AU513017B2 (enExample) |
| CA (1) | CA1100896A (enExample) |
| DE (1) | DE2733202A1 (enExample) |
| DK (1) | DK347077A (enExample) |
| FR (1) | FR2369343A1 (enExample) |
| GB (1) | GB1542028A (enExample) |
| IT (1) | IT1116790B (enExample) |
| NL (1) | NL7708633A (enExample) |
| SE (1) | SE7708845L (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2446859A1 (fr) * | 1979-01-22 | 1980-08-14 | Solvay | Procede de separation de poly-b-hydroxybutyrates d'une biomasse |
| US4336334A (en) * | 1979-02-21 | 1982-06-22 | Imperial Chemical Industries Limited | Microbiological process for the production of poly(β-hydroxybutyric acid) |
| GB2063873B (en) * | 1979-11-06 | 1983-10-05 | Kanegafuchi Chemical Ind | Fermentative production of d(-)-hydroxyisobutyric acid |
| FR2486072A1 (fr) * | 1980-07-03 | 1982-01-08 | Solvay | Procede pour la fabrication de l'acide b-hydroxybutyrique et de ses oligocondensats |
| EP0046344B1 (en) * | 1980-08-19 | 1985-06-19 | Imperial Chemical Industries Plc | Fermentation process |
| US4568644A (en) * | 1981-12-10 | 1986-02-04 | Massachusetts Institute Of Technology | Fermentation method producing ethanol |
| FR2521857B1 (fr) * | 1982-02-23 | 1985-10-31 | Solvay | Compositions pharmaceutiques contenant de l'acide 3-hydroxybutanoique ou un sel derive de cet acide et sels derives de l'acide 3-hydroxybutanoique et d'une base organique azotee |
| DE3375024D1 (en) * | 1982-03-16 | 1988-02-04 | Kanegafuchi Chemical Ind | Process for producing d-beta-hydroxyalkanoic acid |
| GB2126082A (en) * | 1982-08-12 | 1984-03-21 | Heinrich Schulze | Pharmaceutical preparations having analgetic and cytostatic activity |
| US4642290A (en) * | 1982-12-06 | 1987-02-10 | Sih Charles J | Process for preparing a compound for use in the production of L-carnitine |
| US4710468A (en) * | 1983-10-24 | 1987-12-01 | Sigma-Tau Industrie Pharmaceutiche Riunite S.P.A. | Process for preparing L-carnitine and chemical intermediates employed therein |
| US4981794A (en) * | 1984-01-27 | 1991-01-01 | E. R. Squibb & Sons, Inc. | Method of preparing D(-)-β-hydroxyisobutyric acid by fermentation |
| US5334520A (en) * | 1990-05-25 | 1994-08-02 | Center For Innovative Technology | Production of poly-beta-hydroxybutyrate in transformed escherichia coli |
| US5518907A (en) * | 1989-06-07 | 1996-05-21 | Center For Innovative Technology | Cloning and expression in Escherichia coli of the Alcaligenes eutrophus H16 poly-beta-hydroxybutyrate biosynthetic pathway |
| US5302525A (en) * | 1992-11-23 | 1994-04-12 | National Research Council Of Canada | Methylobacterium extorquwns microorganism useful for the preparation of poly-β-hydroxybutyric acid polymers |
| US20090253781A1 (en) * | 2002-05-24 | 2009-10-08 | Btg International Limited | Therapeutic compositions |
| US6323237B1 (en) * | 1997-03-17 | 2001-11-27 | Btg International Limited | Therapeutic compositions |
| AU2002219818B2 (en) | 2000-11-20 | 2007-08-16 | Cargill, Incorporated | 3-hydroxypropionic acid and other organic compounds |
| US7816514B2 (en) | 2001-02-16 | 2010-10-19 | Cargill, Incorporated | Glucosamine and method of making glucosamine from microbial biomass |
| US7923437B2 (en) * | 2001-02-16 | 2011-04-12 | Cargill, Incorporated | Water soluble β-glucan, glucosamine, and N-acetylglucosamine compositions and methods for making the same |
| US8222232B2 (en) * | 2001-02-16 | 2012-07-17 | Cargill, Incorporated | Glucosamine and N-acetylglucosamine compositions and methods of making the same fungal biomass |
| CN100577628C (zh) * | 2002-03-25 | 2010-01-06 | 嘉吉有限公司 | 制造β-羟基羧酸衍生物的方法 |
| GB0420856D0 (en) * | 2004-09-20 | 2004-10-20 | Ketocytonyx Inc | Cns modulators |
| WO2006020137A2 (en) | 2004-07-16 | 2006-02-23 | Ketocytonyx Inc. | Oligomeric compounds |
| WO2006020179A2 (en) * | 2004-07-20 | 2006-02-23 | Ketocytonyx Inc. | Oligomeric ketone compounds |
| EP1778212A4 (en) * | 2004-07-23 | 2010-12-08 | Btg Int Ltd | SACCHARIDES CETOGENES |
| US20070197645A1 (en) * | 2004-09-21 | 2007-08-23 | Martin Keith F | Treatment of adhd |
| ES2574557T3 (es) * | 2004-09-21 | 2016-06-20 | Btg International Limited | Miméticos dopaminérgicos |
| US7693829B1 (en) * | 2005-04-25 | 2010-04-06 | Google Inc. | Search engine with fill-the-blanks capability |
| DE102008002715A1 (de) * | 2008-06-27 | 2009-12-31 | Evonik Röhm Gmbh | 2-Hydroxyisobuttersäure produzierende rekombinante Zelle |
| US9944586B2 (en) | 2013-10-17 | 2018-04-17 | Cargill, Incorporated | Methods for producing alkyl hydroxyalkanoates |
| WO2016061356A1 (en) | 2014-10-17 | 2016-04-21 | Cargill, Incorporated | Methods for producing an ester of an alpha, beta-unsaturated carboxylic acid |
| CN107709542B (zh) * | 2015-07-29 | 2021-08-17 | 赢创运营有限公司 | 3-羟基丁酸的生产 |
| JP6692229B2 (ja) * | 2016-06-28 | 2020-05-13 | 大阪瓦斯株式会社 | ３ｈｂエステルの製造方法 |
| GB201616058D0 (en) * | 2016-09-21 | 2016-11-02 | Chain Biotechnology Ltd | Probiotic composition |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3036959A (en) * | 1960-09-26 | 1962-05-29 | Grace W R & Co | Process for preparing poly-beta-hydroxy-butyric acid |
| US3044942A (en) * | 1960-09-27 | 1962-07-17 | Grace W R & Co | Process for preparing poly-beta-hydroxybutyric acid |
-
1977
- 1977-07-22 DE DE19772733202 patent/DE2733202A1/de not_active Withdrawn
- 1977-08-03 SE SE7708845A patent/SE7708845L/xx not_active Application Discontinuation
- 1977-08-03 GB GB7732573A patent/GB1542028A/en not_active Expired
- 1977-08-03 DK DK347077A patent/DK347077A/da unknown
- 1977-08-03 CA CA283,963A patent/CA1100896A/en not_active Expired
- 1977-08-04 US US05/821,858 patent/US4211846A/en not_active Expired - Lifetime
- 1977-08-04 JP JP9406177A patent/JPS5318794A/ja active Pending
- 1977-08-04 IT IT68803/77A patent/IT1116790B/it active
- 1977-08-04 FR FR7724059A patent/FR2369343A1/fr active Granted
- 1977-08-04 NL NL7708633A patent/NL7708633A/xx unknown
- 1977-08-07 AU AU27636/77A patent/AU513017B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5318794A (en) | 1978-02-21 |
| SE7708845L (sv) | 1978-02-05 |
| US4211846A (en) | 1980-07-08 |
| CA1100896A (en) | 1981-05-12 |
| IT1116790B (it) | 1986-02-10 |
| DK347077A (da) | 1978-02-05 |
| FR2369343A1 (fr) | 1978-05-26 |
| AU513017B2 (en) | 1980-11-06 |
| AU2763677A (en) | 1979-02-08 |
| FR2369343B3 (enExample) | 1980-06-06 |
| GB1542028A (en) | 1979-03-14 |
| NL7708633A (nl) | 1978-02-07 |
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