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WO2008038050A3 - Reduction of alpha-halo ketones - Google Patents

Reduction of alpha-halo ketones Download PDF

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Publication number
WO2008038050A3
WO2008038050A3 PCT/GB2007/050590 GB2007050590W WO2008038050A3 WO 2008038050 A3 WO2008038050 A3 WO 2008038050A3 GB 2007050590 W GB2007050590 W GB 2007050590W WO 2008038050 A3 WO2008038050 A3 WO 2008038050A3
Authority
WO
WIPO (PCT)
Prior art keywords
alpha
halo
reduction
ketones
halo ketones
Prior art date
Application number
PCT/GB2007/050590
Other languages
French (fr)
Other versions
WO2008038050A2 (en
Inventor
Jonathan Wiffen
Brian Adger
Original Assignee
Almac Sciences Ltd
Jonathan Wiffen
Brian Adger
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 Almac Sciences Ltd, Jonathan Wiffen, Brian Adger filed Critical Almac Sciences Ltd
Publication of WO2008038050A2 publication Critical patent/WO2008038050A2/en
Publication of WO2008038050A3 publication Critical patent/WO2008038050A3/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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy 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
    • 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
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/04—Alpha- or beta- amino acids
    • C12P13/22—Tryptophan; Tyrosine; Phenylalanine; 3,4-Dihydroxyphenylalanine
    • C12P13/222—Phenylalanine
    • 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
    • C12P41/004—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 alcohol- or thiol groups in the enantiomers or the inverse reaction

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (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)
  • Analytical Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

The present invention relates to a method for reducing alpha-halo ketones to alpha-halo alcohols. More specifically, the present invention is concerned with the use of isolated enzymes for reduction of alpha-halo ketones to corresponding alpha-halo alcohols. The alpha-halo alcohol is obtained in good yield from the corresponding ketone in a stereoselective manner. The reaction is conducted in the presence of an isolated enzyme or a resting cell.
PCT/GB2007/050590 2006-09-29 2007-09-28 Reduction of alpha-halo ketones WO2008038050A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0619240.5 2006-09-29
GB0619240A GB0619240D0 (en) 2006-09-29 2006-09-29 Reduction of alpha-halo ketones

Publications (2)

Publication Number Publication Date
WO2008038050A2 WO2008038050A2 (en) 2008-04-03
WO2008038050A3 true WO2008038050A3 (en) 2008-06-26

Family

ID=37434924

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2007/050590 WO2008038050A2 (en) 2006-09-29 2007-09-28 Reduction of alpha-halo ketones

Country Status (2)

Country Link
GB (1) GB0619240D0 (en)
WO (1) WO2008038050A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011005527A2 (en) 2009-06-22 2011-01-13 Codexis, Inc. Ketoreductase-mediated stereoselective route to alpha chloroalcohols
WO2011100265A2 (en) 2010-02-10 2011-08-18 Codexis, Inc. Processes using amino acid dehydrogenases and ketoreductase-based cofactor regenerating system
DE102012017026A1 (en) 2012-08-28 2014-03-06 Forschungszentrum Jülich GmbH Sensor for NADP (H) and development of alcohol dehydrogenases
WO2017001907A1 (en) * 2015-06-29 2017-01-05 Teva Pharmaceuticals International Gmbh Biocatalytic processes for the preparation of vilanterol
CN113185429B (en) * 2021-04-12 2023-06-06 江苏海洋大学 Preparation method of anti-HIV protease inhibitor intermediate

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0779366A1 (en) * 1995-06-19 1997-06-18 Kaneka Corporation Process for producing optically active 1-halo-3-amino-4-phenyl-2-butanol derivatives
USH1893H (en) * 1996-07-23 2000-10-03 Bristol-Myers Squibb Company Enzymatic reduction method for the preparation of halohydrins
WO2006013801A1 (en) * 2004-08-06 2006-02-09 Kaneka Corporation Novel carbonyl reductase, gene thereof and method of using the same
WO2006061137A1 (en) * 2004-12-09 2006-06-15 Wacker Chemie Ag Gdh mutant having improved chemical stability
WO2006127180A1 (en) * 2005-05-25 2006-11-30 Bristol-Myers Squibb Company A process for preparing (2r,3s)-1,2-epoxy-3-(protected)amino-4-substituted butane and intermediates thereof

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0779366A1 (en) * 1995-06-19 1997-06-18 Kaneka Corporation Process for producing optically active 1-halo-3-amino-4-phenyl-2-butanol derivatives
USH1893H (en) * 1996-07-23 2000-10-03 Bristol-Myers Squibb Company Enzymatic reduction method for the preparation of halohydrins
WO2006013801A1 (en) * 2004-08-06 2006-02-09 Kaneka Corporation Novel carbonyl reductase, gene thereof and method of using the same
EP1792986A1 (en) * 2004-08-06 2007-06-06 Kaneka Corporation Novel carbonyl reductase, gene thereof and method of using the same
WO2006061137A1 (en) * 2004-12-09 2006-06-15 Wacker Chemie Ag Gdh mutant having improved chemical stability
WO2006127180A1 (en) * 2005-05-25 2006-11-30 Bristol-Myers Squibb Company A process for preparing (2r,3s)-1,2-epoxy-3-(protected)amino-4-substituted butane and intermediates thereof

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DATABASE CAPLUS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 14 October 2003 (2003-10-14), KATAOKA ET AL.: "Conjugated polyketone reductase from Candida parapsilosis", XP002465384, retrieved from STN accession no. 2003:804796 *
KALUZNA ET AL: "Ketoreductases: stereoselective catalysts for the facile synthesis of chiral alcohols", TETRAHEDRON: ASYMMETRY, PERGAMON, OXFORD, GB, vol. 16, no. 22, 14 November 2005 (2005-11-14), pages 3682 - 3689, XP005180018, ISSN: 0957-4166 *
PATEL R N ET AL: "Diastereoselective microbial reduction of (S)-[3-chloro-2-oxo-1-(phen ylmethyl)propyl]carbamic acid, 1,1-dimethylethyl ester", TETRAHEDRON: ASYMMETRY, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 14, no. 20, 17 October 2003 (2003-10-17), pages 3105 - 3109, XP004464019, ISSN: 0957-4166 *
PATEL R N: "BIOCATALYTIC SYNTHESIS OF CHIRAL INTERMEDIATES FOR ANTIVIRAL AND ANTIHYPERTENSIVE DRUGS", JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY, AOCS PRESS, CHAMPAIGN, IL, US, vol. 76, no. 11, 1999, pages 1275 - 1281, XP002946859, ISSN: 0003-021X *

Also Published As

Publication number Publication date
GB0619240D0 (en) 2006-11-08
WO2008038050A2 (en) 2008-04-03

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