WO2005123932A3 - Process for the preparation of optically active alpha-substituted carboxylic acids or alpha-substituted carboxylic acid amides from enantiomeric mixtures of alpha-substituted carboxylic acid amides employing pseudomonas fluorescens - Google Patents

Process for the preparation of optically active alpha-substituted carboxylic acids or alpha-substituted carboxylic acid amides from enantiomeric mixtures of alpha-substituted carboxylic acid amides employing pseudomonas fluorescens Download PDF

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Publication number
WO2005123932A3
WO2005123932A3 PCT/GB2005/002302 GB2005002302W WO2005123932A3 WO 2005123932 A3 WO2005123932 A3 WO 2005123932A3 GB 2005002302 W GB2005002302 W GB 2005002302W WO 2005123932 A3 WO2005123932 A3 WO 2005123932A3
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WO
WIPO (PCT)
Prior art keywords
carboxylic acid
alpha
substituted carboxylic
acid amides
optically active
Prior art date
Application number
PCT/GB2005/002302
Other languages
French (fr)
Other versions
WO2005123932A2 (en
Inventor
Keith Hazell
Robert Antony Holt
Stuart Richard Rigby
Original Assignee
Avecia Pharmaceuticals Ltd
Keith Hazell
Robert Antony Holt
Stuart Richard Rigby
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 Avecia Pharmaceuticals Ltd, Keith Hazell, Robert Antony Holt, Stuart Richard Rigby filed Critical Avecia Pharmaceuticals Ltd
Publication of WO2005123932A2 publication Critical patent/WO2005123932A2/en
Publication of WO2005123932A3 publication Critical patent/WO2005123932A3/en

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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
    • C12P7/40—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
    • C12P11/00—Preparation of sulfur-containing organic compounds
    • 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
    • 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

Abstract

There is provided a process for the preparation of an optically active carboxylic acid or an optically active carboxylic acid amide wherein a carboxylic acid amide having an alpha-carbon substituted with a heteroatom group is enantioselectively hydrolysed in the presence of an enzyme obtainable from Pseudomonas fluorescens to give an optically active carboxylic acid or an optically active carboxylic acid amide. The carboxylic acid amide is preferably a carboxylic acid amide of formula (1): wherein R1 and R2 each independently are hydrogen or a substituent group; and R3 is an optionally substituted heteroatom group; provided that R1, R2 and R3 are different, and the carboxylic acid is preferably a carboxylic acid of formula (4): wherein R1 and R2 each independently are hydrogen or a substituent group; and R3 is an optionally substituted heteroatom group; provided that R1, R2 and R3 are different such that * is a chiral centre.
PCT/GB2005/002302 2004-06-15 2005-06-10 Process for the preparation of optically active alpha-substituted carboxylic acids or alpha-substituted carboxylic acid amides from enantiomeric mixtures of alpha-substituted carboxylic acid amides employing pseudomonas fluorescens WO2005123932A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB0413322A GB0413322D0 (en) 2004-06-15 2004-06-15 Process
GB0413322.9 2004-06-15

Publications (2)

Publication Number Publication Date
WO2005123932A2 WO2005123932A2 (en) 2005-12-29
WO2005123932A3 true WO2005123932A3 (en) 2006-04-27

Family

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Family Applications (1)

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PCT/GB2005/002302 WO2005123932A2 (en) 2004-06-15 2005-06-10 Process for the preparation of optically active alpha-substituted carboxylic acids or alpha-substituted carboxylic acid amides from enantiomeric mixtures of alpha-substituted carboxylic acid amides employing pseudomonas fluorescens

Country Status (2)

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GB (1) GB0413322D0 (en)
WO (1) WO2005123932A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3944726A1 (en) * 2020-07-23 2022-01-26 AT & S Austria Technologie & Systemtechnik Aktiengesellschaft Component carrier with protruding thermally conductive tongue and corresponding method of manufacturing

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4080259A (en) * 1976-01-08 1978-03-21 Novo Industri A/S Process of preparing L and D α-amino acids by enzyme treatment of DL-α-amino acid amide
EP0043211A2 (en) * 1980-06-24 1982-01-06 Ube Industries, Ltd. Process for preparing optically active tryptophanes
US4443548A (en) * 1981-05-14 1984-04-17 Ube Industries, Ltd. Process for preparing L-α-methylphenyl alanines
EP0172614A1 (en) * 1984-08-16 1986-02-26 Mitsubishi Rayon Co., Ltd. Process for producing optically active carboxylic acid amides
EP0348901A2 (en) * 1988-06-27 1990-01-03 Asahi Kasei Kogyo Kabushiki Kaisha Process for producing optically active alfa-substituted organic acid and microorganism and enzyme used therefor
EP0654533A2 (en) * 1993-11-18 1995-05-24 Mitsubishi Rayon Co., Ltd. A process for producing D-lactic acid and L-lactamide
WO2003106689A1 (en) * 2002-06-05 2003-12-24 鐘淵化学工業株式会社 PROCESS FOR PRODUCING OPTICALLY ACTIVE α-METHYLCYSTEINE DERIVATIVE

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4080259A (en) * 1976-01-08 1978-03-21 Novo Industri A/S Process of preparing L and D α-amino acids by enzyme treatment of DL-α-amino acid amide
EP0043211A2 (en) * 1980-06-24 1982-01-06 Ube Industries, Ltd. Process for preparing optically active tryptophanes
US4443548A (en) * 1981-05-14 1984-04-17 Ube Industries, Ltd. Process for preparing L-α-methylphenyl alanines
EP0172614A1 (en) * 1984-08-16 1986-02-26 Mitsubishi Rayon Co., Ltd. Process for producing optically active carboxylic acid amides
EP0348901A2 (en) * 1988-06-27 1990-01-03 Asahi Kasei Kogyo Kabushiki Kaisha Process for producing optically active alfa-substituted organic acid and microorganism and enzyme used therefor
EP0654533A2 (en) * 1993-11-18 1995-05-24 Mitsubishi Rayon Co., Ltd. A process for producing D-lactic acid and L-lactamide
WO2003106689A1 (en) * 2002-06-05 2003-12-24 鐘淵化学工業株式会社 PROCESS FOR PRODUCING OPTICALLY ACTIVE α-METHYLCYSTEINE DERIVATIVE
EP1550725A1 (en) * 2002-06-05 2005-07-06 Kaneka Corporation PROCESS FOR PRODUCING OPTICALLY ACTIVE alpha-METHYLCYSTEINE DERIVATIVE

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Derwent World Patents Index; AN 2004-180159, XP002360878 *

Also Published As

Publication number Publication date
WO2005123932A2 (en) 2005-12-29
GB0413322D0 (en) 2004-07-14

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