CA2428163A1 - Process for the enzymatic preparation of enantiomer-enriched .beta.-amino acids - Google Patents
Process for the enzymatic preparation of enantiomer-enriched .beta.-amino acids Download PDFInfo
- Publication number
- CA2428163A1 CA2428163A1 CA002428163A CA2428163A CA2428163A1 CA 2428163 A1 CA2428163 A1 CA 2428163A1 CA 002428163 A CA002428163 A CA 002428163A CA 2428163 A CA2428163 A CA 2428163A CA 2428163 A1 CA2428163 A1 CA 2428163A1
- Authority
- CA
- Canada
- Prior art keywords
- beta
- process according
- amino acid
- enriched
- reaction
- 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.)
- Granted
Links
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
- C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
- C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
- C12P41/005—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of carboxylic acid groups in the enantiomers or the inverse reaction
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Analytical Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a process for preparing enantiomer-enriched .beta.-amino acids by enzymatic ester resolution of N-unprotected .beta.-amino acid esters in a two-phase system composed of water and an organic solvent forming two phases with water under the given reaction conditions.
Claims (8)
1. Process for producing enantiomer-enriched N-unprotected, in particular open-chain .beta.-amino acids by enzymatic hydrolysis of an enantiomeric mixture of N-unprotected, in particular open-chain .beta.-amino acid esters with a hydrolase, wherein the hydrolysis takes place in a two-phase system composed of water and an organic solvent forming two phases with water under the given reaction conditions.
2. Process according to Claim 1, characterized in that a .beta.-amino acid alkyl ester or a .beta.-amino acid aryl ester is used.
3. Process according to Claim 2, characterized in that an appropriate n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tent-butyl ester is used.
4. Process according to one or more of the preceding claims, characterized in that the pH of the reaction is between 4 and 10, preferably between 6 and 9 and more preferably between 7 and 8.5.
5. Process according to one or more of the preceding claims, characterized in that the temperature during the reaction is between -15 and +100°C, preferably between +15 and +40°C and more preferably between +20 and +30°C.
6. Process according to one or more of the preceding claims, characterized in that a lipase, preferably the lipase PS from Pseudomonas cepacia is used.
7. Process according to one or more of the preceding claims, characterized in that the reaction is performed in an enzyme membrane reactor.
8. Process according to one or more of the preceding claims, characterized in that ethers, ketones, esters, saturated or unsaturated linear or branched-chain hydrocarbons are used as organic solvent.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10220740.2 | 2002-05-08 | ||
DE10220740A DE10220740A1 (en) | 2002-05-08 | 2002-05-08 | Production of enantiomer enriched N-unprotected beta-aminoacids, useful for production of pharmaceuticals, comprises enzymatic hydrolysis of beta-aminoacid esters with hydrolase in two-phase system of water and organic solvent |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2428163A1 true CA2428163A1 (en) | 2003-11-08 |
CA2428163C CA2428163C (en) | 2011-08-09 |
Family
ID=29285247
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2428163A Expired - Fee Related CA2428163C (en) | 2002-05-08 | 2003-05-07 | Process for the enzymatic preparation of enantiomer-enriched .beta.-amino acids |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP1367129B1 (en) |
JP (1) | JP4662694B2 (en) |
KR (1) | KR101043190B1 (en) |
CN (1) | CN1327002C (en) |
AT (1) | ATE435299T1 (en) |
CA (1) | CA2428163C (en) |
DE (2) | DE10220740A1 (en) |
HR (1) | HRP20030356A2 (en) |
IL (1) | IL155784A (en) |
SG (1) | SG120092A1 (en) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2853327B1 (en) * | 2003-04-04 | 2012-07-27 | Solvay | PROCESS FOR THE PRODUCTION OF ENANTIOPOR BETA-AMINOACID DERIVATIVES AND ENANTIOPA BETA-AMINOACIDIC DERIVATIVES |
ATE361905T1 (en) * | 2003-12-10 | 2007-06-15 | Degussa | METHOD FOR PRODUCING ENANTIOMERIC ENRICHED AMINO ACIDS |
CN1926241A (en) * | 2004-02-27 | 2007-03-07 | 帝斯曼知识产权资产管理有限公司 | Enzymatic preparation of an enantiomerically enriched beta-2-amino acids |
JP4608938B2 (en) * | 2004-05-12 | 2011-01-12 | 宇部興産株式会社 | Process for producing optically active 3-alkyl-3-arylpropionic acid and optically active 3-alkyl-3-arylpropionic acid alkyl ester |
JP4608963B2 (en) * | 2004-06-22 | 2011-01-12 | 宇部興産株式会社 | Process for producing optically active 3-aryl-3-hydroxypropionic acid and optically active 3-aryl-3-hydroxypropionic acid alkyl ester |
CN101040053B (en) * | 2004-10-08 | 2013-04-24 | 宇部兴产株式会社 | Process for production of optically active (S)- or (R)- beta-amino acids and optically active (R)- or (S)-beta -amino acid esters, and beta-amino acid 2-alkoxyethyl ester and optically active (s or r)-beta amino acid 2-alkoxyethyl ester |
DE102004057966A1 (en) * | 2004-11-30 | 2006-06-01 | Degussa Ag | Method for asymmetrical enzymatic production of optically active organic compounds in microemulsion |
JPWO2006123689A1 (en) * | 2005-05-17 | 2008-12-25 | 宇部興産株式会社 | Method for producing carboxylic acid using surfactant-modifying enzyme |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2927535A1 (en) * | 1979-07-07 | 1981-01-08 | Bayer Ag | STEREOSELECTIVE CUTTING OF PHENYLGLYCINE DERIVATIVES WITH ENZYME RESINS |
US4636470A (en) * | 1984-08-17 | 1987-01-13 | Stauffer Chemical Company | Resolution of racemates of amino acids |
-
2002
- 2002-05-08 DE DE10220740A patent/DE10220740A1/en not_active Withdrawn
-
2003
- 2003-04-09 SG SG200302077A patent/SG120092A1/en unknown
- 2003-05-06 HR HR20030356A patent/HRP20030356A2/en not_active Application Discontinuation
- 2003-05-06 IL IL155784A patent/IL155784A/en not_active IP Right Cessation
- 2003-05-07 CN CNB031234283A patent/CN1327002C/en not_active Expired - Fee Related
- 2003-05-07 KR KR1020030028856A patent/KR101043190B1/en not_active IP Right Cessation
- 2003-05-07 AT AT03010226T patent/ATE435299T1/en not_active IP Right Cessation
- 2003-05-07 CA CA2428163A patent/CA2428163C/en not_active Expired - Fee Related
- 2003-05-07 EP EP03010226A patent/EP1367129B1/en not_active Expired - Lifetime
- 2003-05-07 DE DE50311645T patent/DE50311645D1/en not_active Expired - Lifetime
- 2003-05-08 JP JP2003130565A patent/JP4662694B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
IL155784A (en) | 2010-06-30 |
DE10220740A1 (en) | 2003-11-27 |
IL155784A0 (en) | 2003-12-23 |
EP1367129B1 (en) | 2009-07-01 |
CA2428163C (en) | 2011-08-09 |
EP1367129A2 (en) | 2003-12-03 |
JP2003325197A (en) | 2003-11-18 |
DE50311645D1 (en) | 2009-08-13 |
JP4662694B2 (en) | 2011-03-30 |
EP1367129A3 (en) | 2003-12-17 |
SG120092A1 (en) | 2006-03-28 |
CN1327002C (en) | 2007-07-18 |
ATE435299T1 (en) | 2009-07-15 |
HRP20030356A2 (en) | 2004-04-30 |
KR20030087562A (en) | 2003-11-14 |
KR101043190B1 (en) | 2011-06-22 |
CN1456676A (en) | 2003-11-19 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKLA | Lapsed |
Effective date: 20180507 |