WO2006015727A3 - Verfahren zur enantioselektiven öffnung von 3-substituierten oxetan-2-onen unter einwirkung der lipasen von candida antarctica oder burkholderia plantarii - Google Patents

Verfahren zur enantioselektiven öffnung von 3-substituierten oxetan-2-onen unter einwirkung der lipasen von candida antarctica oder burkholderia plantarii Download PDF

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Publication number
WO2006015727A3
WO2006015727A3 PCT/EP2005/008190 EP2005008190W WO2006015727A3 WO 2006015727 A3 WO2006015727 A3 WO 2006015727A3 EP 2005008190 W EP2005008190 W EP 2005008190W WO 2006015727 A3 WO2006015727 A3 WO 2006015727A3
Authority
WO
WIPO (PCT)
Prior art keywords
burkholderia
candida antarctica
substituted
plantarrii
enantioselectively
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.)
Ceased
Application number
PCT/EP2005/008190
Other languages
English (en)
French (fr)
Other versions
WO2006015727A2 (de
Inventor
Tilo Habicher
Rainer Stuermer
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.)
BASF SE
Original Assignee
BASF SE
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
Priority claimed from DE200410038589 external-priority patent/DE102004038589A1/de
Application filed by BASF SE filed Critical BASF SE
Priority to DE502005002868T priority Critical patent/DE502005002868D1/de
Priority to US11/659,139 priority patent/US7582469B2/en
Priority to EP05769677A priority patent/EP1805314B1/de
Priority to CN2005800260050A priority patent/CN1993472B/zh
Priority to JP2007524236A priority patent/JP4607182B2/ja
Publication of WO2006015727A2 publication Critical patent/WO2006015727A2/de
Publication of WO2006015727A3 publication Critical patent/WO2006015727A3/de
Anticipated expiration legal-status Critical
Ceased 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
    • C12P41/001—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by metabolizing one of the enantiomers
    • 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
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atoms
    • 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
    • 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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group
    • 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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
    • 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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/62—Carboxylic acid esters

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (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)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)

Abstract

Verfahren zur Herstellung von im wesentlichen enantiomerenreinen 3-Hydroxycarbonsäuren bzw. -estern der allgemeinen Formel (III) indem man racemische Oxetan-2-one der allgemeinen Formel (I) mit Verbindungen R3-OH der allgemeinen Formel (II) in Gegenwart einer Lipase aus Candida antartica oder Burkholderia plantarii ) umsetzt und die erhaltenen Produkte der Formel (III) und (IV) voneinander trennt wobei die Reste folgende Bedeutung aufweisen: R1, R2 , R3 unabhängig voneinander H; C1-C10-substituiertes oder unsubstituiertes Alkyl, substituiertes oder unsubstituiertes Aryl oder Hetaryl, wobei R1 und R2 nicht gleichzeitig diesselbe Bedeutung besitzen dürfen.
PCT/EP2005/008190 2004-08-02 2005-07-28 Verfahren zur enantioselektiven öffnung von 3-substituierten oxetan-2-onen unter einwirkung der lipasen von candida antarctica oder burkholderia plantarii Ceased WO2006015727A2 (de)

Priority Applications (5)

Application Number Priority Date Filing Date Title
DE502005002868T DE502005002868D1 (de) 2004-08-02 2005-07-28 Verfahren zur enantioselektiven öffnung von 3-substituierten oxetan-2-onen unter verwendung der lipasen von candida antarctica oder von burkholderia plantarii
US11/659,139 US7582469B2 (en) 2004-08-02 2005-07-28 Method for enantioselectively opening oxetan-2-ones
EP05769677A EP1805314B1 (de) 2004-08-02 2005-07-28 Verfahren zur enantioselektiven öffnung von 3-substituierten oxetan-2-onen unter verwendung der lipasen von candida antarctica oder von burkholderia plantarii
CN2005800260050A CN1993472B (zh) 2004-08-02 2005-07-28 在南极洲假丝酵母或伯克霍尔德氏菌的作用下对映选择性地打开3位取代的氧杂环丁-2-酮的方法
JP2007524236A JP4607182B2 (ja) 2004-08-02 2005-07-28 オキセタン−２−オンのエナンチオ選択的な開環法

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE102004037700.6 2004-08-02
DE102004037700A DE102004037700A1 (de) 2004-08-02 2004-08-02 Verfahren zur enantioselektiven Öffnung von Oxetan-2-onen
DE200410038589 DE102004038589A1 (de) 2004-08-06 2004-08-06 Verfahren zur enantioselektiven Öffnung von Oxetan-2-onen
DE102004038589.0 2004-08-06

Publications (2)

Publication Number Publication Date
WO2006015727A2 WO2006015727A2 (de) 2006-02-16
WO2006015727A3 true WO2006015727A3 (de) 2006-07-13

Family

ID=35610182

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2005/008190 Ceased WO2006015727A2 (de) 2004-08-02 2005-07-28 Verfahren zur enantioselektiven öffnung von 3-substituierten oxetan-2-onen unter einwirkung der lipasen von candida antarctica oder burkholderia plantarii

Country Status (7)

Country Link
US (1) US7582469B2 (de)
EP (1) EP1805314B1 (de)
JP (1) JP4607182B2 (de)
CN (1) CN1993472B (de)
AT (1) ATE386132T1 (de)
DE (2) DE102004037700A1 (de)
WO (1) WO2006015727A2 (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2551350A1 (de) * 2011-07-27 2013-01-30 Lonza Ltd Verfahren zur Herstellung von L-Carnitin aus ß-Lactonen unter Verwendung von Lipasen
CN115232801B (zh) * 2022-07-07 2024-03-12 河南工业大学 一种耐高温碱性脂肪酶及其制备方法和应用
CN115819221B (zh) * 2022-12-15 2024-05-10 上海馨远医药科技有限公司 一种(r)-2-羟甲基丙酸和(s)-2-羟甲基丙酸的制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5767276A (en) 1995-10-13 1998-06-16 The Penn State Research Foundation Asymmetric synthesis catalyzed by transition metal complexes with new chiral ligands

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
ADAM, W. ET AL.: "Enzymatic preparation of optically active alpha-methylene beta-lactones by lipase-catalyzed kinetic resolution through asymmetric transesterification", TETRAHEDRON: ASYMMETRY, vol. 8, no. 6, 27 March 1997 (1997-03-27), pages 833 - 836, XP004056867 *
ITO, T. ET AL.: "Preparation and Use of Novel (S)-beta-Chlorodifluoromethyl-beta-propi olactone as a Chiral Fluorinated Building Block", TETRAHEDRON, vol. 54, no. 21, 21 May 1998 (1998-05-21), pages 5523 - 5530, XP004118405 *
SAKAI, N. ET AL.: "Lipase promoted asymmetric trans-esterification of 4-alkyl-, 3-alkyl- and 3,4-dialkyloxetan-2-ones with ring-opening", JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS I, no. 1, 2000, pages 71 - 77, XP002372025 *

Also Published As

Publication number Publication date
DE102004037700A1 (de) 2006-03-16
US7582469B2 (en) 2009-09-01
DE502005002868D1 (de) 2008-03-27
US20080311633A1 (en) 2008-12-18
WO2006015727A2 (de) 2006-02-16
EP1805314A2 (de) 2007-07-11
JP2008507984A (ja) 2008-03-21
CN1993472B (zh) 2012-06-06
ATE386132T1 (de) 2008-03-15
CN1993472A (zh) 2007-07-04
EP1805314B1 (de) 2008-02-13
JP4607182B2 (ja) 2011-01-05

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