AR126002A1 - Método enzimático para la producción de p-alquil ésteres de l-glufosinato - Google Patents
Método enzimático para la producción de p-alquil ésteres de l-glufosinatoInfo
- Publication number
- AR126002A1 AR126002A1 ARP220101427A ARP220101427A AR126002A1 AR 126002 A1 AR126002 A1 AR 126002A1 AR P220101427 A ARP220101427 A AR P220101427A AR P220101427 A ARP220101427 A AR P220101427A AR 126002 A1 AR126002 A1 AR 126002A1
- Authority
- AR
- Argentina
- Prior art keywords
- glufosinate
- alkyl ester
- hydantoin
- carbamoylase
- mixture
- Prior art date
Links
- IAJOBQBIJHVGMQ-BYPYZUCNSA-N glufosinate-P Chemical compound CP(O)(=O)CC[C@H](N)C(O)=O IAJOBQBIJHVGMQ-BYPYZUCNSA-N 0.000 title abstract 10
- 238000006911 enzymatic reaction Methods 0.000 title abstract 3
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 abstract 4
- 229940091173 hydantoin Drugs 0.000 abstract 4
- 238000000034 method Methods 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- IAJOBQBIJHVGMQ-SCSAIBSYSA-N (2R)-glufosinate Chemical compound C[P@@](O)(=O)CC[C@@H](N)C(O)=O IAJOBQBIJHVGMQ-SCSAIBSYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 108010088443 hydantoin racemase Proteins 0.000 abstract 2
- IVWWFWFVSWOTLP-YVZVNANGSA-N (3'as,4r,7'as)-2,2,2',2'-tetramethylspiro[1,3-dioxolane-4,6'-4,7a-dihydro-3ah-[1,3]dioxolo[4,5-c]pyran]-7'-one Chemical compound C([C@@H]1OC(O[C@@H]1C1=O)(C)C)O[C@]21COC(C)(C)O2 IVWWFWFVSWOTLP-YVZVNANGSA-N 0.000 abstract 1
- -1 D-glufosinate hydantoins Chemical class 0.000 abstract 1
- 102100036238 Dihydropyrimidinase Human genes 0.000 abstract 1
- 108010011945 N-carbamoyl-L-amino-acid hydrolase Proteins 0.000 abstract 1
- 108091022884 dihydropyrimidinase Proteins 0.000 abstract 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
- C12P13/04—Alpha- or beta- amino acids
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/78—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5)
- C12N9/80—Hydrolases (3) acting on carbon to nitrogen bonds other than peptide bonds (3.5) acting on amide bonds in linear amides (3.5.1)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/90—Isomerases (5.)
-
- 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
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y305/00—Hydrolases acting on carbon-nitrogen bonds, other than peptide bonds (3.5)
- C12Y305/01—Hydrolases acting on carbon-nitrogen bonds, other than peptide bonds (3.5) in linear amides (3.5.1)
- C12Y305/01087—N-Carbamoyl-L-amino-acid hydrolase (3.5.1.87)
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y305/00—Hydrolases acting on carbon-nitrogen bonds, other than peptide bonds (3.5)
- C12Y305/02—Hydrolases acting on carbon-nitrogen bonds, other than peptide bonds (3.5) in cyclic amides (3.5.2)
- C12Y305/02002—Dihydropyrimidinase (3.5.2.2), i.e. hydantoinase
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y501/00—Racemaces and epimerases (5.1)
- C12Y501/99—Racemaces and epimerases (5.1) acting on other compounds (5.1.99)
- C12Y501/99005—Hydantoin racemase (5.1.99.5)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
La presente invención se refiere en un primer aspecto a un método enzimático para la producción de un P-alquil éster de L-glufosinato. Este método se caracteriza mediante una etapa (c) en la que un carbamoilato de P-alquil éster de L-glufosinato se hace reaccionar para proporcionar el correspondiente P-alquil éster de L-glufosinato. Esta etapa (c) se cataliza mediante a carbamoilasa, con preferencia mediante una carbamoilasa L-enantioselectiva. El carbamoilato de P-alquil éster de L-glufosinato empleado en la etapa (c) se puede obtener mediante la reacción del correspondiente P-alquil éster de L-glufosinato hidantoína. Esta etapa antecedente opcional (b) se cataliza mediante una hidantoinasa, con preferencia una carbamoilasa L-enantioselectiva. Incluso con más preferencia, el P-alquil éster de L-glufosinato hidantoína empleado en la etapa (b) se puede obtener mediante la reacción del correspondiente P-alquil éster de D-glufosinato hidantoína. Esta etapa antecedente opcional (a) con preferencia se cataliza mediante una hidantoína racemasa. En un segundo aspecto, la presente invención se refiere a un método enzimático para la producción enantioselectiva de un P-alquil éster de L-glufosinato de una mezcla MIIIA P-alquil éster de L- y D-glufosinato hidantoínas. En el método de acuerdo con el segundo aspecto de la invención, la mezcla MIIIA se proporciona en una etapa (i-A) y se emplea en las etapas (ii) y (iii). Las etapas (ii) y (iii) corresponden a las etapas (b) y (c) descriptas anteriormente, respectivamente, donde en la etapa (c), se usa una L-carbamoilasa. En una etapa preferida opcional (i-B) del método de acuerdo con el segundo aspecto de la invención, correspondiente a la etapa preferida (a) descripta anteriormente, con preferencia se usa una hidantoína racemasa para convertir al menos una parte del P-alquil éster de D-glufosinato hidantoína en la mezcla MIIIA en su correspondiente L-enantiómero, lo que proporciona una mezcla MIIIB, que luego se emplea en las etapas (ii) y (iii). El P-alquil éster de L-glufosinato obtenido en los métodos de acuerdo con el primer o segundo aspecto de la invención se puede saponificar para dar L-glufosinato.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP21179773.3A EP4105335A1 (en) | 2021-06-16 | 2021-06-16 | Enzymatic method for the production of l-glufosinate p-alkyl esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR126002A1 true AR126002A1 (es) | 2023-08-30 |
Family
ID=76807464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP220101427A AR126002A1 (es) | 2021-06-16 | 2022-05-31 | Método enzimático para la producción de p-alquil ésteres de l-glufosinato |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20240287558A1 (es) |
| EP (2) | EP4105335A1 (es) |
| CN (1) | CN117545849A (es) |
| AR (1) | AR126002A1 (es) |
| CA (1) | CA3224036A1 (es) |
| MX (1) | MX2023014864A (es) |
| PE (1) | PE20240891A1 (es) |
| WO (1) | WO2022248739A1 (es) |
| ZA (1) | ZA202400351B (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023232225A1 (en) * | 2022-05-31 | 2023-12-07 | Evonik Operations Gmbh | Enzymatic method for the diastereoselective production of l-glufosinate p-esters |
| WO2024175643A1 (en) * | 2023-02-23 | 2024-08-29 | Basf Se | A process for preparing l-glufosinate from cyanhydrine or cyanhydrine derivatives |
| CN118581169A (zh) * | 2023-03-01 | 2024-09-03 | 湖南利尔生物科技有限公司 | 一种从l-高丝氨酸直接制备l-草铵膦的方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3142036A1 (de) | 1981-10-23 | 1983-05-05 | Hoechst Ag, 6230 Frankfurt | Phosphorhaltige hydantoine, verfahren zu deren herstellung und ihre verwendung |
| US5795776A (en) | 1994-03-22 | 1998-08-18 | Bio-Technology General Corp. | Expression plasmids regulated by an OSMB promoter |
| US6524837B1 (en) | 1999-03-29 | 2003-02-25 | California Institute Of Technology | Hydantoinase variants with improved properties and their use for the production of amino acids |
| DE10031999A1 (de) | 1999-09-09 | 2001-04-19 | Degussa | Verfahren zur fermentativen Herstellung von D-Pantothensäure unter Verwendung coryneformer Bakterien |
| US6713288B1 (en) | 1999-09-28 | 2004-03-30 | University Of Stuttgart | Whole cell catalysts |
| DE10251184A1 (de) | 2002-11-04 | 2004-05-13 | Degussa Ag | Mutanten zur Herstellung von D-Aminosäuren |
| US7247465B2 (en) | 2003-06-06 | 2007-07-24 | Degussa Ag | Screening process for hydantoin racemases |
| EP2102353A2 (en) * | 2006-12-04 | 2009-09-23 | DSM IP Assets B.V. | Whole-cell catalytic system comprising a hydantoinase, a racemase and a carbamoylase |
| JP6279478B2 (ja) | 2011-11-16 | 2018-02-14 | エボニック テクノヘミー ゲゼルシャフト ミット ベシュレンクテル ハフツングＥｖｏｎｉｋ Ｔｅｃｈｎｏｃｈｅｍｉｅ ＧｍｂＨ | ヒダントイナーゼの突然変異体 |
| EP3423585A1 (en) | 2016-03-02 | 2019-01-09 | Agrimetis, LLC | Methods for making l-glufosinate |
| CN106083922B (zh) | 2016-08-23 | 2018-08-31 | 山东省农药科学研究院 | 一种精草铵膦的制备方法 |
| WO2019018406A1 (en) | 2017-07-18 | 2019-01-24 | Agrimetis, Llc | METHODS OF PURIFYING L-GLUFOSINATE |
| CN108516991A (zh) | 2018-05-28 | 2018-09-11 | 山东省农药科学研究院 | 一种精草铵膦的制备方法 |
| US20210214754A1 (en) | 2018-09-05 | 2021-07-15 | Basf Se | Methods for improving yields of l-glufosinate |
| KR102582675B1 (ko) | 2019-01-11 | 2023-09-25 | 씨제이제일제당 주식회사 | 글루포시네이트 제조 방법 |
| KR102183111B1 (ko) | 2019-01-11 | 2020-11-25 | 씨제이제일제당 (주) | L-글루포시네이트 중간체 및 l-글루포시네이트 제조 방법 |
| CN111662325B (zh) | 2019-03-05 | 2023-03-24 | 利尔化学股份有限公司 | 一种制备l-草铵膦的方法 |
-
2021
- 2021-06-16 EP EP21179773.3A patent/EP4105335A1/en not_active Withdrawn
-
2022
- 2022-05-31 EP EP22731552.0A patent/EP4355893A1/en active Pending
- 2022-05-31 AR ARP220101427A patent/AR126002A1/es unknown
- 2022-05-31 MX MX2023014864A patent/MX2023014864A/es unknown
- 2022-05-31 CN CN202280042776.2A patent/CN117545849A/zh active Pending
- 2022-05-31 US US18/569,989 patent/US20240287558A1/en active Pending
- 2022-05-31 PE PE2023003272A patent/PE20240891A1/es unknown
- 2022-05-31 WO PCT/EP2022/064682 patent/WO2022248739A1/en active Application Filing
- 2022-05-31 CA CA3224036A patent/CA3224036A1/en active Pending
-
2024
- 2024-01-10 ZA ZA2024/00351A patent/ZA202400351B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA3224036A1 (en) | 2022-12-01 |
| EP4355893A1 (en) | 2024-04-24 |
| EP4105335A1 (en) | 2022-12-21 |
| US20240287558A1 (en) | 2024-08-29 |
| PE20240891A1 (es) | 2024-04-24 |
| MX2023014864A (es) | 2024-01-16 |
| CN117545849A (zh) | 2024-02-09 |
| WO2022248739A1 (en) | 2022-12-01 |
| ZA202400351B (en) | 2024-06-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AR126002A1 (es) | Método enzimático para la producción de p-alquil ésteres de l-glufosinato | |
| WO2020051188A8 (en) | Methods for improving yields of l-glufosinate | |
| AR122914A1 (es) | Método para la producción fermentativa de ácido guanidinoacético | |
| AR122886A1 (es) | Método para la producción fermentativa de ácido guanidinoacético | |
| WO2021002484A3 (ja) | 除草剤及びその中間体の製造方法 | |
| BRPI0401812A (pt) | Métodos para produzir um dicarboxilato de cadaverina, e, náilon | |
| AR128755A1 (es) | Método enzimático para la producción de p-ésteres de l-glufosinato | |
| EA200501016A1 (ru) | Способ получения кристаллических форм и кристаллические формы оптических энантиомеров модафинила | |
| ATE479644T1 (de) | Verfahren zur umesterung von estern | |
| DE602005012597D1 (de) | Verfahren zur herstellung optisch aktiver n-carbamat-geschützter beta-lactame durch optische auflösung unter verwendung einer candida antarctica lipase | |
| NO20065068L (no) | Membran og fremgangsmate for fremstilling av slik | |
| ATE37861T1 (de) | Verfahren zur herstellung einer freien alpha-laminos|ure. | |
| DE60304175D1 (de) | Verfahren zur herstellung von losartan und losartan-kaliumsalz | |
| SG120092A1 (en) | Process for the enzymatic preparation of enantiomer-enriched beta-amino acids | |
| AR018967A1 (es) | Proceso para la reduccion microbiana estereoselectiva de una tetralona racemica. | |
| WO2023287814A3 (en) | Carboxylic acid platform for fuel and chemical production at high carbon and energy efficiency | |
| US7994342B2 (en) | Method for producing optically active succinimide compound | |
| DK1119634T3 (da) | Enzymkatalyseret racematspaltning af primære aminer | |
| Strübing et al. | Enzymatic resolution of 4-N-phenylacetylamino-derivatives obtained from multicomponent reactions using PenG amidase and in silico studies | |
| DK1140826T3 (da) | Fremgangsmåde til fremstilling af (2S,4R,9S)-octahydro-1H-indol-2-carbonsyre og mellemprodukter dertil | |
| WO2001044492A3 (de) | Verfahren zur kinetischen racematspaltung von alkoholen oder carbonsäureestern | |
| Kim et al. | A practical method to cleave diphenyl phosphonate esters to their corresponding phosphonic acids in one step | |
| MX2023014874A (es) | Composiciones y métodos para la síntesis enzimática de ácidos nucleicos. | |
| EP1887005A4 (en) | METHODS FOR PREPARING PPAR-ACTIVATED OPTICALLY ACTIVE COMPOUNDS AND INTERMEDIATES FOR THEIR PREPARATION | |
| WO2002022849A3 (en) | Enzymatic resolution of aryl- and thio-substituted acids |