DE102004037669A1 - (R)- und (S)-1,4-Dichlor-butan-2-ol und Verfahren zu deren Herstellung durch enantioselektive enzymatische Reduktion von 1,4-Dichlor-butan-2-on - Google Patents

(R)- und (S)-1,4-Dichlor-butan-2-ol und Verfahren zu deren Herstellung durch enantioselektive enzymatische Reduktion von 1,4-Dichlor-butan-2-on Download PDF

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Publication number
DE102004037669A1
DE102004037669A1 DE102004037669A DE102004037669A DE102004037669A1 DE 102004037669 A1 DE102004037669 A1 DE 102004037669A1 DE 102004037669 A DE102004037669 A DE 102004037669A DE 102004037669 A DE102004037669 A DE 102004037669A DE 102004037669 A1 DE102004037669 A1 DE 102004037669A1
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butan
dichloro
nadh
nadph
new
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Antje Gupta
Anke Zimmer
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Cambrex IEP GmbH
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IEP GmbH
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    • 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
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
    • C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
    • C12P7/16—Butanols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/34—Halogenated alcohols
    • C07C31/36—Halogenated alcohols the halogen not being fluorine
    • 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
    • C12P7/26—Ketones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel

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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)

Abstract

Beschrieben sind (R)-1,4-Dichlor-butan-2-ol und (S)-1,4-Dichlor-butan-2-ol sowie ein Verfahren zu deren Herstellung aus 1,4-Dichlor-butan-2-on durch enzymatische Reduktion in Gegenwart einer Dehydrogenase/Oxidoreduktase mit NADH oder NADPH als Cofaktor in einem wäßrigen System enzymatisch. Vorzugsweise wird der Cofaktor dabei mit Hilfe eines Cosubstrats kontinuierlich regeneriert. Offenbart ist daneben ein Verfahren zur enantioselektiven Oxidation eines racemische Gemisches von (R)- und (S)-1,4-Dichlor-butan-2-ol mit einer Oxidoreduktase/Dehydrogenase, NAD oder NADP in einem wäßrigen System. Das nicht oxidierte Enantiomer läßt sich dann isolieren. Die enzymatische Reduktion bzw. Oxidation kann in einem Zweiphasensystem durchgeführt werden. In diesem Fall wird vorzugsweise in mit Wasser nicht oder nur beschränkt mischbares organisches Lösungsmittel, beispielsweise Diethylether, Ethylacetat, Butylacetat oder Hexan, zugefügt.
DE102004037669A 2003-08-13 2004-08-04 (R)- und (S)-1,4-Dichlor-butan-2-ol und Verfahren zu deren Herstellung durch enantioselektive enzymatische Reduktion von 1,4-Dichlor-butan-2-on Withdrawn DE102004037669A1 (de)

Priority Applications (1)

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DE102004037669A DE102004037669A1 (de) 2003-08-13 2004-08-04 (R)- und (S)-1,4-Dichlor-butan-2-ol und Verfahren zu deren Herstellung durch enantioselektive enzymatische Reduktion von 1,4-Dichlor-butan-2-on

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10337401 2003-08-13
DE102004037669A DE102004037669A1 (de) 2003-08-13 2004-08-04 (R)- und (S)-1,4-Dichlor-butan-2-ol und Verfahren zu deren Herstellung durch enantioselektive enzymatische Reduktion von 1,4-Dichlor-butan-2-on

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DE102004037669A1 true DE102004037669A1 (de) 2005-03-10

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1582518A1 (de) * 2004-03-31 2005-10-05 Daiso Co., Ltd. Verfahren zur Herstellung von 3-Hydroxythiolane
DE102006009744A1 (de) * 2006-03-02 2007-09-06 Wacker Chemie Ag Herstellung von (S)-2-Butanol durch oxidative Racematspaltung
US8404461B2 (en) 2009-10-15 2013-03-26 SK Biopharmaceutical Co. Ltd. Method for preparation of carbamic acid (R)-1-aryl-2-tetrazolyl-ethyl ester
US8501436B2 (en) 2009-06-22 2013-08-06 Sk Biopharmaceuticals Co. Ltd. Method for preparation of carbamic acid (R)-1-aryl-2-tetrazolyl-ethyl ester

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1582518A1 (de) * 2004-03-31 2005-10-05 Daiso Co., Ltd. Verfahren zur Herstellung von 3-Hydroxythiolane
US7262310B2 (en) 2004-03-31 2007-08-28 Daiso Co., Ltd. Process for preparing 3-hydroxythiolane
DE102006009744A1 (de) * 2006-03-02 2007-09-06 Wacker Chemie Ag Herstellung von (S)-2-Butanol durch oxidative Racematspaltung
US8501436B2 (en) 2009-06-22 2013-08-06 Sk Biopharmaceuticals Co. Ltd. Method for preparation of carbamic acid (R)-1-aryl-2-tetrazolyl-ethyl ester
US8404461B2 (en) 2009-10-15 2013-03-26 SK Biopharmaceutical Co. Ltd. Method for preparation of carbamic acid (R)-1-aryl-2-tetrazolyl-ethyl ester
US9068207B2 (en) 2009-10-15 2015-06-30 Sk Biopharmaceuticals Co. Ltd. Method for preparation of carbamic acid (R)-1-aryl-2-tetrazolyl-ethyl ester
US9434970B2 (en) 2009-10-15 2016-09-06 Sk Biopharmaceuticals Co., Ltd. Method for preparation of carbamic acid (R)-1-aryl-2-tetrazolyl-ethyl ester

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Owner name: IEP GMBH, 65203 WIESBADEN, DE

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