EA200801878A1 - ENZYMATIC METHOD FOR SEPARATION OF RACECHIC 3-ARYL-4-AMINO-OIL ACID - Google Patents

ENZYMATIC METHOD FOR SEPARATION OF RACECHIC 3-ARYL-4-AMINO-OIL ACID

Info

Publication number
EA200801878A1
EA200801878A1 EA200801878A EA200801878A EA200801878A1 EA 200801878 A1 EA200801878 A1 EA 200801878A1 EA 200801878 A EA200801878 A EA 200801878A EA 200801878 A EA200801878 A EA 200801878A EA 200801878 A1 EA200801878 A1 EA 200801878A1
Authority
EA
Eurasian Patent Office
Prior art keywords
aryl
aminobutyric acid
pyrrolidone
separation
racechic
Prior art date
Application number
EA200801878A
Other languages
Russian (ru)
Other versions
EA014980B1 (en
Inventor
Григорий Вейнберг
Максим Ворона
Антонс Лебедевс
Александрс Чернобровыйс
Иварс Калвиньш
Original Assignee
Акционерное Общество "Олайнфарм"
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 Акционерное Общество "Олайнфарм" filed Critical Акционерное Общество "Олайнфарм"
Publication of EA200801878A1 publication Critical patent/EA200801878A1/en
Publication of EA014980B1 publication Critical patent/EA014980B1/en

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
    • C12P13/001—Amines; Imines
    • 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
    • C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
    • 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
    • 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
    • C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Genetics & Genomics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Изобретение относится к энзиматическому разделению R- и S-энантиомеров рацемического эфира 3-арил-4-аминомасляной кислоты, в котором арильная группа представлена фенилом (фенибут) или пара-хлорфенилом (баклофен), а сложноэфирная группа представлена насыщенной или ненасыщенной алкильной группой, содержащей от 2 до 8 углеродных атомов. Патентуемый метод получения состоит из следующих этапов: (1) селективная циклизация (S)-энантиомера рацемического эфира 3-арил-4-аминомасляной кислоты в 4(S)-арил-2-пирролидон в водном растворе в присутствии α-химотрипсина; (2) разделение 4(S)-арил-2-пирролидона и эфира 3(R)-арил-4-аминомасляной кислоты экстракцией после подкисления реакционной смеси до pH<2,0; (3) выделения 4(S)-арил-2-пирролидона из органической фазы и 3(R)-арил-4-аминомасляной кислоты из водной фазы и их последующее превращение в R- и S-стереоизомеры 3-арил-4-аминомасляной кислоты с помощью гидролиза в кислой среде.The invention relates to the enzymatic separation of the R- and S-enantiomers of the racemic 3-aryl-4-aminobutyric acid ester, in which the aryl group is represented by phenyl (phenibut) or para-chlorophenyl (baclofen), and the ester group is represented by a saturated or unsaturated alkyl group containing from 2 to 8 carbon atoms. The patented production method consists of the following steps: (1) selective cyclization of the (S) -enantiomer of racemic 3-aryl-4-aminobutyric acid ester to 4 (S) -aryl-2-pyrrolidone in an aqueous solution in the presence of α-chymotrypsin; (2) separating 4 (S) -aryl-2-pyrrolidone and 3 (R) -aryl-4-aminobutyric acid ester by extraction after acidifying the reaction mixture to pH <2.0; (3) isolation of 4 (S) -aryl-2-pyrrolidone from the organic phase and 3 (R) -aryl-4-aminobutyric acid from the aqueous phase and their subsequent transformation into the R- and S-stereoisomers of 3-aryl-4-aminobutyric acid acid by acid hydrolysis.

EA200801878A 2006-02-23 2007-02-18 A process for enzymatic resolution of racemic 3-aryl-4-aminobutyric acid EA014980B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
LV060028A LV13635B (en) 2006-02-23 2006-02-23 Enzymatic resolution of racemic 3-aryl-4-aminobutyric acids
PCT/EP2007/051538 WO2007096314A2 (en) 2006-02-23 2007-02-18 Enzymatic resolution of racemic 3-aryl-4-aminobutyric acid

Publications (2)

Publication Number Publication Date
EA200801878A1 true EA200801878A1 (en) 2009-04-28
EA014980B1 EA014980B1 (en) 2011-04-29

Family

ID=38375630

Family Applications (1)

Application Number Title Priority Date Filing Date
EA200801878A EA014980B1 (en) 2006-02-23 2007-02-18 A process for enzymatic resolution of racemic 3-aryl-4-aminobutyric acid

Country Status (3)

Country Link
EA (1) EA014980B1 (en)
LV (1) LV13635B (en)
WO (1) WO2007096314A2 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5380743B2 (en) * 2008-06-19 2014-01-08 住友化学株式会社 Process for producing optically active 4-amino-3-substituted phenylbutanoic acid
LV15015B (en) 2013-12-13 2015-12-20 Olainfarm, A/S Salt of 3-carboxy-4-(r)-phenylpyrrolidinone-2 and uses thereof
FR3054218B1 (en) * 2016-07-22 2020-03-06 Universite De Rouen PROCESS FOR SPLITTING BACLOFENE SALTS
CN115282928B (en) * 2022-08-04 2023-08-15 杭州佳嘉乐生物技术有限公司 Novel separation medium and application thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6051734A (en) * 1995-12-20 2000-04-18 Farmarc Nederland B.V. Process for the optical resolution of 3-(p-chlorophenyl)-glutaramide
US5843765A (en) * 1997-01-31 1998-12-01 National Research Council Of Canada Streptomyces microorganism useful for the preparation of (R)-baclofen from the racemic mixture

Also Published As

Publication number Publication date
LV13635B (en) 2008-01-20
WO2007096314A3 (en) 2007-11-01
WO2007096314A2 (en) 2007-08-30
EA014980B1 (en) 2011-04-29

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Legal Events

Date Code Title Description
MM4A Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s)

Designated state(s): AM AZ KG MD TJ TM

MM4A Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s)

Designated state(s): BY KZ RU