CA1323593C - Process for the enzymatic preparation of l-2-amino-4- methylphosphinobutyric acid - Google Patents
Process for the enzymatic preparation of l-2-amino-4- methylphosphinobutyric acidInfo
- Publication number
- CA1323593C CA1323593C CA000572951A CA572951A CA1323593C CA 1323593 C CA1323593 C CA 1323593C CA 000572951 A CA000572951 A CA 000572951A CA 572951 A CA572951 A CA 572951A CA 1323593 C CA1323593 C CA 1323593C
- Authority
- CA
- Canada
- Prior art keywords
- amino
- carried out
- aqueous
- acid
- immobilized
- 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 description 19
- 230000002255 enzymatic effect Effects 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- NIBLDNQQTIFBAI-BYPYZUCNSA-N CPCC[C@H](N)C(O)=O Chemical compound CPCC[C@H](N)C(O)=O NIBLDNQQTIFBAI-BYPYZUCNSA-N 0.000 title 1
- 241000588724 Escherichia coli Species 0.000 claims abstract description 9
- 229920001661 Chitosan Polymers 0.000 claims abstract description 6
- NIBLDNQQTIFBAI-UHFFFAOYSA-N 2-amino-4-methylphosphanylbutanoic acid Chemical compound CPCCC(N)C(O)=O NIBLDNQQTIFBAI-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000011534 incubation Methods 0.000 claims description 5
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims 1
- 239000002609 medium Substances 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 8
- 108700023418 Amidases Proteins 0.000 abstract description 2
- 102000005922 amidase Human genes 0.000 abstract description 2
- 108090000790 Enzymes Proteins 0.000 description 14
- 102000004190 Enzymes Human genes 0.000 description 14
- 239000011942 biocatalyst Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000758 substrate Substances 0.000 description 5
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 108010073038 Penicillin Amidase Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- IYNDLOXRXUOGIU-LQDWTQKMSA-M benzylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 IYNDLOXRXUOGIU-LQDWTQKMSA-M 0.000 description 3
- IAJOBQBIJHVGMQ-BYPYZUCNSA-N glufosinate-P Chemical compound CP(O)(=O)CC[C@H](N)C(O)=O IAJOBQBIJHVGMQ-BYPYZUCNSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229960003424 phenylacetic acid Drugs 0.000 description 2
- 239000003279 phenylacetic acid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000228212 Aspergillus Species 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- HDNWUBCAQKQFCJ-RZVRUWJTSA-N N[C@H](C(=O)O)CCPC.N[C@H](C(=O)O)CCPC Chemical compound N[C@H](C(=O)O)CCPC.N[C@H](C(=O)O)CCPC HDNWUBCAQKQFCJ-RZVRUWJTSA-N 0.000 description 1
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N Phosphinothricin Natural products CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 230000007515 enzymatic degradation Effects 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
-
- 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino 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
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures
- C12P41/007—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures by reactions involving acyl derivatives of racemic amines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Genetics & Genomics (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP3724722.0 | 1987-07-25 | ||
| DE19873724722 DE3724722A1 (de) | 1987-07-25 | 1987-07-25 | Verbessertes verfahren zur enzymatischen herstellung von l-2-amino-4-methylphosphinobuttersaeure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1323593C true CA1323593C (en) | 1993-10-26 |
Family
ID=6332382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000572951A Expired - Fee Related CA1323593C (en) | 1987-07-25 | 1988-07-25 | Process for the enzymatic preparation of l-2-amino-4- methylphosphinobutyric acid |
Country Status (14)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0382114B1 (de) * | 1989-02-06 | 1996-10-23 | Hoechst Schering AgrEvo GmbH | Phosphinesterhaltige N-Acyl-2-aminosäureamide, Verfahren zu ihrer Herstellung und N-Acyl-2-aminosäurenitrile als Vorprodukte |
| DE3903446A1 (de) * | 1989-02-06 | 1990-10-18 | Hoechst Ag | Verfahren zur enzymatischen trennung von 2-amino-4-methylphosphinobuttersaeurederivaten |
| IL101539A (en) | 1991-04-16 | 1998-09-24 | Monsanto Europe Sa | Non-hygroscopic mono-ammonium salts of n-phosphonomethyl glycine derivatives their preparation and pesticidal compositons containing them |
| EG22838A (en) * | 2000-08-28 | 2003-09-30 | Dsm Nv | Process for the preparation of a b-lactam nucleus and application thereof |
| WO2003072792A2 (en) * | 2002-02-26 | 2003-09-04 | Syngenta Limited | A method of selectively producing male or female sterile plants |
| CN112940031B (zh) * | 2021-02-01 | 2022-08-02 | 河北威远生物化工有限公司 | 一种n-萘乙酰草铵膦及其合成方法及以其合成l-草铵膦的合成方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1369462A (en) * | 1971-11-23 | 1974-10-09 | Beecham Group Ltd | Enzymic resolution of racemic n-acyl-dl-amino acids |
| JPS5547630A (en) * | 1978-10-02 | 1980-04-04 | Meiji Seika Kaisha Ltd | Optical resolution of phosphorus-containing amino acid |
| DE3005632C2 (de) * | 1980-02-15 | 1985-06-05 | Joachim Prof. Dr. Klein | Verfahren zur Herstellung von Biokatalysatoren mit hoher mechanischer Festigkeit und hoher Beladung an enzymatisch aktiver Substanz |
| DE3048612C2 (de) * | 1980-12-23 | 1982-12-02 | Hoechst Ag, 6000 Frankfurt | "Verfahren zur enzymatischen Trennung von L-2-Ami no-4-methylphosphinobuttersäure" |
| DE3903446A1 (de) * | 1989-02-06 | 1990-10-18 | Hoechst Ag | Verfahren zur enzymatischen trennung von 2-amino-4-methylphosphinobuttersaeurederivaten |
-
1987
- 1987-07-25 DE DE19873724722 patent/DE3724722A1/de not_active Withdrawn
-
1988
- 1988-07-20 DE DE8888111636T patent/DE3878499D1/de not_active Expired - Fee Related
- 1988-07-20 AT AT88111636T patent/ATE85814T1/de not_active IP Right Cessation
- 1988-07-20 EP EP88111636A patent/EP0301391B1/de not_active Expired - Lifetime
- 1988-07-20 ES ES198888111636T patent/ES2039515T3/es not_active Expired - Lifetime
- 1988-07-21 HU HU883800A patent/HU202589B/hu not_active IP Right Cessation
- 1988-07-21 ZA ZA885295A patent/ZA885295B/xx unknown
- 1988-07-22 DK DK412088A patent/DK412088A/da not_active Application Discontinuation
- 1988-07-22 AU AU19733/88A patent/AU606185B2/en not_active Ceased
- 1988-07-22 DD DD88318210A patent/DD272476A5/de unknown
- 1988-07-22 JP JP63181946A patent/JPS6451099A/ja active Pending
- 1988-07-23 KR KR1019880009265A patent/KR890002411A/ko not_active Ceased
- 1988-07-25 CA CA000572951A patent/CA1323593C/en not_active Expired - Fee Related
- 1988-07-26 IL IL87218A patent/IL87218A/xx not_active IP Right Cessation
-
1993
- 1993-04-27 GR GR930400606T patent/GR3007701T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUT50214A (en) | 1989-12-28 |
| DK412088D0 (da) | 1988-07-22 |
| DE3878499D1 (de) | 1993-03-25 |
| DD272476A5 (de) | 1989-10-11 |
| JPS6451099A (en) | 1989-02-27 |
| KR890002411A (ko) | 1989-04-10 |
| GR3007701T3 (enrdf_load_stackoverflow) | 1993-08-31 |
| AU606185B2 (en) | 1991-01-31 |
| ZA885295B (en) | 1989-03-29 |
| ES2039515T3 (es) | 1993-10-01 |
| EP0301391A1 (de) | 1989-02-01 |
| DK412088A (da) | 1989-01-26 |
| HU202589B (en) | 1991-03-28 |
| IL87218A (en) | 1992-01-15 |
| IL87218A0 (en) | 1988-12-30 |
| AU1973388A (en) | 1989-04-20 |
| EP0301391B1 (de) | 1993-02-17 |
| ATE85814T1 (de) | 1993-03-15 |
| DE3724722A1 (de) | 1989-02-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |