Nothing Special   »   [go: up one dir, main page]

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

Info

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

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/003Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/005Processes 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
    • CCHEMISTRY; METALLURGY
    • C12BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12PFERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00Preparation of nitrogen-containing organic compounds
    • C12P13/04Alpha- 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Enzymes And Modification 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
JP4361094B2 (en) * 2003-12-10 2009-11-11 エボニック デグサ ゲーエムベーハー Method for producing enantiomerically enriched amino acids
WO2005085462A1 (en) * 2004-02-27 2005-09-15 Dsm Ip Assets B.V. 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
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
DE102004057966A1 (en) * 2004-11-30 2006-06-01 Degussa Ag Method for asymmetrical enzymatic production of optically active organic compounds in microemulsion
CN101180402A (en) * 2005-05-17 2008-05-14 宇部兴产株式会社 Process for production of 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
EP1367129A2 (en) 2003-12-03
CN1327002C (en) 2007-07-18
HRP20030356A2 (en) 2004-04-30
KR20030087562A (en) 2003-11-14
CA2428163C (en) 2011-08-09
EP1367129A3 (en) 2003-12-17
CN1456676A (en) 2003-11-19
ATE435299T1 (en) 2009-07-15
DE10220740A1 (en) 2003-11-27
IL155784A (en) 2010-06-30
KR101043190B1 (en) 2011-06-22
DE50311645D1 (en) 2009-08-13
EP1367129B1 (en) 2009-07-01
JP2003325197A (en) 2003-11-18
IL155784A0 (en) 2003-12-23
JP4662694B2 (en) 2011-03-30
SG120092A1 (en) 2006-03-28

Similar Documents

Publication Publication Date Title
NZ603659A (en) Production of alcohol esters and in situ product removal during alcohol fermentation
Skrobo et al. Enzymatic approaches for the preparation of optically active non-centrochiral compounds
CA2428163A1 (en) Process for the enzymatic preparation of enantiomer-enriched .beta.-amino acids
Watanabe et al. Dimethyl sulfoxide as a co-solvent dramatically enhances the enantioselectivity in lipase-catalysed resolutions of 2-phenoxypropionic acyl derivatives
Jin et al. Enzymatic production of enantiopure ketoprofen in a solvent-free two-phase system
Lokotsch et al. Resolution of D, L-menthol by interesterification with triacetin using the free and immobilized lipase of Candida cylindracea
Solares et al. Enzymatic resolution of a quaternary stereogenic centre as the key step in the synthesis of (S)-(+)-citalopram
Okamoto et al. Drastic enhancement of the enantioselectivity of lipase-catalysed esterification in organic solvents by the addition of metal ions
Rustoy et al. Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid
JP5266875B2 (en) Process for producing optically active organic carboxylic acid from organic carboxylic acid ester
JP6169812B2 (en) Method for producing L-carnitine from beta-lactone using lipase
JP2009005682A (en) Process for producing optically active 2-alkyl-1,1,3-trialkoxycarbonylpropane
Okamoto et al. A new method for improving the enantioselectivity of lipase-catalyzed hydrolysis in organic solvent containing a small amount of water in the presence of metal ions
JP4042454B2 (en) Process for producing optically active 3-methylglutaric acid monoester
JP2005287511A (en) Method for enzymatically synthesizing triglyceride of unsaturated fatty acid
Sánchez et al. Enantioselective esterification of 2-arylpropionic acids and trans-2-phenyl-1-cyclohexanol: Comparison between immobilised lipases from Candida rugosa and Rhizomucor miehei
Zheng et al. Chemoenzymatic synthesis of d-biotin intermediate lactone via lipase-catalyzed desymmetrization of meso diols
Shimojo et al. Enzyme-mediated enantioselective hydrolysis of poly (ethylene glycol)-supported carbonates
CA2111595A1 (en) Process for the enzymatic preparation of optically active transglycidic acid esters
Lin et al. The enhancement of enantioselectivities for lipase-catalyzed reactions by using carbamates
Miyazawa et al. Resolution of 2-cyano-2-methylalkanoic acids via porcine pancreatic lipase-catalyzed enantioselective ester hydrolysis: effect of the alcohol moiety of the substrate ester on enantioselectivity
Ko et al. Kinetic resolution of fluorinated propargyl alcohols by lipase-catalyzed enantioselective transesterification
Banerjee et al. Ionic liquid-mediated biocatalyzed organic transformations
Niwayama Recent desymmetrization reactions by CALB
Yıldız et al. Synthesis of new (R)-secondary carbinols with different structures via enzymatic resolution

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20180507