CA2428059A1 - Process for the enzymatic preparation of enantiomerically enriched beta-amino acids - Google Patents
Process for the enzymatic preparation of enantiomerically enriched beta-amino acids Download PDFInfo
- Publication number
- CA2428059A1 CA2428059A1 CA002428059A CA2428059A CA2428059A1 CA 2428059 A1 CA2428059 A1 CA 2428059A1 CA 002428059 A CA002428059 A CA 002428059A CA 2428059 A CA2428059 A CA 2428059A CA 2428059 A1 CA2428059 A1 CA 2428059A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- process according
- beta
- aryl
- heteroaryl
- 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
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a process for the preparation of enantiomerically enriched .beta.-ammo acids. The invention relates also to advantageous esters of .beta.-amino acids of the general. formula (I) (See Formula I) and to the use thereof in a process for the enzymatic preparation of enantiomerically enriched .beta.-amino acids.
Claims (10)
1. Process for the preparation of enantiomerically enriched N-unprotected .beta.-amino acids by enzymatic hydrolysis of an enantiomeric mixture of N-unprotected .beta.-amino acid esters with a hydrolase, with the proviso that no corresponding methyl or ethyl ester is used.
2. Process according to claim 1, characterised :in that a .beta.-amino acid alkyl ester or .beta.-amino acid aryl ester is used.
3. Process according to claim 2, characterised in that a corresponding n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl ester is used.
4. Process according to one or more of the preceding claims, characterised in that the pH value of the reaction is from 4 to 10, preferably from 6 to 9 and more preferably from 7 to 8.5.
5. Process according to one or more of the preceding claims, characterised in that the temperature in the reaction is from -15 to +100°C, preferably from +15 to +40°C and more preferably from +20 to +30°C.
6. Process according to one or more of the preceding claims, characterised in that a lipase, preferably Lipase PS from Pseudomonas cepacia, is used.
7. Process according to one or more of the preceding claims, characterised in that the reaction is carried out in an enzyme-membrane reactor.
8. Process according to one or more of the preceding claims, characterised in that the hydrolysis is carried out in an aqueous medium, to which water-soluble organic solvents may be added.
9. .beta.-Amino acid n-propyl esters having the following structure (I) wherein R represents (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C3-C8)-cycloalkyl, (C6-C18)-aryl, (C7-C19)-aralkyl, (C3-C18)-heteroaryl, (C4-C19)-heteroaralkyl, ((C1-C8)-alkyl)1-3-(C3-C8)-cycloalkyl, ((C1-C8)-alkyl)1-3-(C6-C18)-aryl, ((C1-C8)-alkyl)1-3-(C3-C18)-heteroaryl, R' represents H, (C1-C8)-alkyl, (C2-C8)-alkenyl, (C2-C8)-alkynyl, (C3-C8)-cycloalkyl, (C6-C18)-aryl, (C7-C19)-aralkyl, (C3-C18)-heteroaryl, (C4-C19)-heteroaralkyl, ((C1-C8)-alkyl)1-3-(C3-C8)-cycloalkyl, ((C1-C8)-alkyl)1-3-(C6-C18)-aryl, ((C1-C8)-alkyl)1-3-(C3-C18)-heteroaryl.
10. Use of the compounds according to claim 9 in a process according to claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10220739.9 | 2002-05-08 | ||
| DE10220739A DE10220739A1 (en) | 2002-05-08 | 2002-05-08 | Process for the enzymatic preparation of enantiomerically enriched β-amino acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2428059A1 true CA2428059A1 (en) | 2003-11-08 |
| CA2428059C CA2428059C (en) | 2011-08-02 |
Family
ID=29225124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2428059A Expired - Fee Related CA2428059C (en) | 2002-05-08 | 2003-05-07 | Process for the enzymatic preparation of enantiomerically enriched beta-amino acids |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP1361279B1 (en) |
| JP (1) | JP4386670B2 (en) |
| KR (1) | KR101172905B1 (en) |
| CN (1) | CN1260364C (en) |
| AT (1) | ATE332391T1 (en) |
| CA (1) | CA2428059C (en) |
| DE (3) | DE10220739A1 (en) |
| DK (1) | DK1361279T3 (en) |
| ES (1) | ES2268212T3 (en) |
| HR (1) | HRP20030357A2 (en) |
| IL (1) | IL155785A0 (en) |
| PT (1) | PT1361279E (en) |
| SG (1) | SG120094A1 (en) |
| SI (1) | SI1361279T1 (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4270991B2 (en) | 2002-10-11 | 2009-06-03 | 株式会社リコー | Information recording apparatus, information recording method, information recording program, storage medium storing information recording program, and information recording system |
| US20060178433A1 (en) * | 2003-03-17 | 2006-08-10 | Yasuhito Yamamoto | 3-Amino-3-arylpropionic acid n-alkyl esters, process for production thereof, and process for production of optically active 3-amino-3-arylpropionic acids and esters of the antipodes thereto |
| 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 |
| WO2005095325A1 (en) * | 2004-03-03 | 2005-10-13 | Degussa Ag | PROCESS FOR THE PREPARATION OF β-AMINOCARBOXYLIC ACIDS |
| JP4893308B2 (en) * | 2004-10-08 | 2012-03-07 | 宇部興産株式会社 | Process for producing optically active (S or R) -β-amino acid and optically active (R or S) -β-amino acid ester, and β-amino acid 2-alkoxyethyl ester and optically active (S or R) -β-amino acid 2 -Alkoxyethyl ester |
| US20090117626A1 (en) * | 2005-05-17 | 2009-05-07 | Hiroyuki Miyata | Process for preparing carboxylic acid using surfactant-modified enzyme |
| EP2796562A4 (en) * | 2011-12-19 | 2015-11-25 | Sumitomo Chemical Co | Method for producing optically-active -substituted- -amino acid |
Family Cites Families (4)
| 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 |
| US5552317A (en) * | 1995-05-26 | 1996-09-03 | Industrial Technology Research Institute | Method for preparing optically active homophenylalanine and esters thereof using lipase from wheat germ or Candida lipolytica |
| AU7349000A (en) * | 1999-08-31 | 2001-03-26 | Qiagen Genomics, Inc. | Enantiomerically-enriched compounds having photocleavable bond(s) and methods related thereto |
-
2002
- 2002-05-08 DE DE10220739A patent/DE10220739A1/en not_active Withdrawn
-
2003
- 2003-04-14 SG SG200302193A patent/SG120094A1/en unknown
- 2003-05-06 HR HR20030357A patent/HRP20030357A2/en not_active Application Discontinuation
- 2003-05-06 IL IL15578503A patent/IL155785A0/en not_active IP Right Cessation
- 2003-05-07 EP EP03010224A patent/EP1361279B1/en not_active Expired - Lifetime
- 2003-05-07 ES ES03010224T patent/ES2268212T3/en not_active Expired - Lifetime
- 2003-05-07 CN CNB031234275A patent/CN1260364C/en not_active Expired - Fee Related
- 2003-05-07 DE DE50304116T patent/DE50304116D1/en not_active Expired - Lifetime
- 2003-05-07 KR KR1020030028937A patent/KR101172905B1/en not_active IP Right Cessation
- 2003-05-07 CA CA2428059A patent/CA2428059C/en not_active Expired - Fee Related
- 2003-05-07 DK DK03010224T patent/DK1361279T3/en active
- 2003-05-07 AT AT03010224T patent/ATE332391T1/en active
- 2003-05-07 SI SI200330469T patent/SI1361279T1/en unknown
- 2003-05-07 PT PT03010224T patent/PT1361279E/en unknown
- 2003-05-07 DE DE10320211A patent/DE10320211A1/en not_active Withdrawn
- 2003-05-08 JP JP2003130566A patent/JP4386670B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003325195A (en) | 2003-11-18 |
| KR101172905B1 (en) | 2012-08-10 |
| EP1361279A1 (en) | 2003-11-12 |
| PT1361279E (en) | 2006-11-30 |
| DE50304116D1 (en) | 2006-08-17 |
| ATE332391T1 (en) | 2006-07-15 |
| DK1361279T3 (en) | 2006-11-06 |
| JP4386670B2 (en) | 2009-12-16 |
| EP1361279B1 (en) | 2006-07-05 |
| HRP20030357A2 (en) | 2004-04-30 |
| SI1361279T1 (en) | 2006-12-31 |
| CA2428059C (en) | 2011-08-02 |
| CN1260364C (en) | 2006-06-21 |
| DE10320211A1 (en) | 2004-02-12 |
| ES2268212T3 (en) | 2007-03-16 |
| KR20030087565A (en) | 2003-11-14 |
| SG120094A1 (en) | 2006-03-28 |
| DE10220739A1 (en) | 2003-11-27 |
| IL155785A0 (en) | 2003-12-23 |
| CN1456675A (en) | 2003-11-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20180507 |