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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 PDF

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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
Application number
CA002428163A
Other languages
French (fr)
Other versions
CA2428163C (en
Inventor
Harald Groeger
Helge Werner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Degussa GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Degussa GmbH filed Critical Degussa GmbH
Publication of CA2428163A1 publication Critical patent/CA2428163A1/en
Application granted granted Critical
Publication of CA2428163C publication Critical patent/CA2428163C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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

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  • 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.
CA2428163A 2002-05-08 2003-05-07 Process for the enzymatic preparation of enantiomer-enriched .beta.-amino acids Expired - Fee Related CA2428163C (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

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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