WO2002101003A3 - Preparation stereoselective de l-acides amines cycliques - Google Patents

Preparation stereoselective de l-acides amines cycliques Download PDF

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Publication number
WO2002101003A3
WO2002101003A3 PCT/FR2002/001983 FR0201983W WO02101003A3 WO 2002101003 A3 WO2002101003 A3 WO 2002101003A3 FR 0201983 W FR0201983 W FR 0201983W WO 02101003 A3 WO02101003 A3 WO 02101003A3
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WO
WIPO (PCT)
Prior art keywords
cyclic
amino acids
stereoselective preparation
formula
diamino acid
Prior art date
Application number
PCT/FR2002/001983
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English (en)
Other versions
WO2002101003A2 (fr
Inventor
Denis Thibaut
Volker Doering
Philippe Marliere
Original Assignee
Rhodia Chimie Sa
Denis Thibaut
Volker Doering
Philippe Marliere
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Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=8864129&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2002101003(A3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Rhodia Chimie Sa, Denis Thibaut, Volker Doering, Philippe Marliere filed Critical Rhodia Chimie Sa
Priority to EP02747526A priority Critical patent/EP1409691A2/fr
Priority to KR1020037016066A priority patent/KR100731597B1/ko
Priority to AU2002317920A priority patent/AU2002317920A1/en
Priority to CA2449836A priority patent/CA2449836C/fr
Priority to JP2003503755A priority patent/JP3943540B2/ja
Priority to US10/479,719 priority patent/US7425530B2/en
Publication of WO2002101003A2 publication Critical patent/WO2002101003A2/fr
Publication of WO2002101003A3 publication Critical patent/WO2002101003A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/88—Lyases (4.)
    • 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
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/10—Nitrogen as only ring hetero atom
    • 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
    • C12P17/10—Nitrogen as only ring hetero atom
    • C12P17/12—Nitrogen as only ring hetero atom containing a six-membered hetero ring
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Biotechnology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Biomedical Technology (AREA)
  • Analytical Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

L'invention concerne un procédé de production d'un L-acide aminé cyclique de formule (I), caractérisé en ce que l'on fait réagir un L-acide diaminé de formule (II), ou un mélange énantiomère comprenant un tel L-acide diaminé et un D-acide diaminé correspondant en proportions variables, en présence d'une ornithine cyclodéaminase ou d'un polypeptide homologue à l'ornithine cyclodéaminase.
PCT/FR2002/001983 2001-06-08 2002-06-10 Preparation stereoselective de l-acides amines cycliques WO2002101003A2 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP02747526A EP1409691A2 (fr) 2001-06-08 2002-06-10 Preparation stereoselective de l-acides amines cycliques
KR1020037016066A KR100731597B1 (ko) 2001-06-08 2002-06-10 환형 ｌ-아미노산의 입체-선택적 제조
AU2002317920A AU2002317920A1 (en) 2001-06-08 2002-06-10 Stereoselective preparation of cyclic l-amino acids
CA2449836A CA2449836C (fr) 2001-06-08 2002-06-10 Preparation stereoselective de l-acides amines cycliques
JP2003503755A JP3943540B2 (ja) 2001-06-08 2002-06-10 環状ｌ−アミノ酸の立体選択的製造
US10/479,719 US7425530B2 (en) 2001-06-08 2002-06-10 Stereoselective preparation of cyclic L-amino acids

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0107559A FR2825717B1 (fr) 2001-06-08 2001-06-08 Preparation stereoselective de l-acides amines cycliques
FR01/07559 2001-06-08

Publications (2)

Publication Number Publication Date
WO2002101003A2 WO2002101003A2 (fr) 2002-12-19
WO2002101003A3 true WO2002101003A3 (fr) 2004-02-26

Family

ID=8864129

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR2002/001983 WO2002101003A2 (fr) 2001-06-08 2002-06-10 Preparation stereoselective de l-acides amines cycliques

Country Status (9)

Country Link
US (1) US7425530B2 (fr)
EP (1) EP1409691A2 (fr)
JP (1) JP3943540B2 (fr)
KR (1) KR100731597B1 (fr)
CN (1) CN100482800C (fr)
AU (1) AU2002317920A1 (fr)
CA (1) CA2449836C (fr)
FR (1) FR2825717B1 (fr)
WO (1) WO2002101003A2 (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003072770A1 (fr) 2002-02-28 2003-09-04 Mitsubishi Chemical Corporation Nouvelle deshydrogenase et gene codant cette derniere
JP4590981B2 (ja) * 2003-08-26 2010-12-01 三菱化学株式会社 光学活性環状アミノ酸の製造方法
CN101423861B (zh) * 2008-07-11 2011-06-15 浙江大学 L-氨基酸衍生物的生物催化制备方法
JP5395395B2 (ja) * 2008-10-10 2014-01-22 北興化学工業株式会社 微生物による環状アミノ酸の製造法
WO2014129459A1 (fr) * 2013-02-19 2014-08-28 株式会社エーピーアイ コーポレーション Procédé de production de la l-lysine hydroxylase et de la hydroxy-l-lysine à l'aide de celle-ci, et procédé de production de l'acide hydroxy-l-pipécolique
WO2015098774A1 (fr) * 2013-12-26 2015-07-02 株式会社カネカ Procédé de production d'imino acide cyclique optiquement actif
CN107286227B (zh) * 2016-03-31 2021-01-05 南京诺云生物科技有限公司 Streptomyces hirsutus ATCC 19091蛋白的新用途
CN107287214A (zh) * 2016-03-31 2017-10-24 南京诺云生物科技有限公司 人工合成的Pseudomonas veronii CIP104663蛋白编码基因及其应用
CN107287256B (zh) * 2016-03-31 2021-06-08 南京诺云生物科技有限公司 全细胞催化合成l-2-哌啶甲酸的方法
CN107287215B (zh) * 2016-03-31 2021-06-29 南京诺云生物科技有限公司 人工合成的Streptomyces hirsutus ATCC 19091蛋白编码基因及其应用
CN107641628A (zh) * 2016-07-20 2018-01-30 南京诺云生物科技有限公司 人工合成的Arenimonas donghaensisi DSM 18418蛋白编码基因及其应用
CN108752253B (zh) * 2018-06-27 2020-11-24 深圳市茵诺圣生物科技有限公司 一种多元氮杂环状非天然手性氨基酸及其合成方法
JP7386616B2 (ja) 2019-04-25 2023-11-27 株式会社エーピーアイ コーポレーション Ｌ体環状アミノ酸の製造方法
CN113512571B (zh) * 2021-07-13 2023-02-24 浙江华睿生物技术有限公司 鸟氨酸环化脱氨酶催化合成l-哌啶酸的方法

Citations (10)

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Publication number Priority date Publication date Assignee Title
JPH0638781A (ja) * 1991-12-11 1994-02-15 Bio-Le Kk １−ピペコリン酸の製造法
JPH0662880A (ja) * 1992-08-10 1994-03-08 Kyowa Hakko Kogyo Co Ltd ４−ヒドロキシ−ｌ−プロリンの製造法
WO1995010604A1 (fr) * 1993-10-15 1995-04-20 Chiroscience Limited Enzyme et son utilisation dans la preparation de l'acide (s) - pipecolique
WO1996001901A1 (fr) * 1994-07-08 1996-01-25 Rhone-Poulenc Rorer S.A. Streptogramines et procede de preparation de streptogramines par mutasynthese
WO1996035775A1 (fr) * 1995-05-08 1996-11-14 Lonza Ag PROCEDE BIOTECHNOLOGIQUE DE PRODUCTION D'ACIDE R-α-CARBOXYLIQUE DE PIPERAZINE ET D'AMIDE D'ACIDE S-α-CARBOXYLIQUE DE PIPERAZINE
JPH10127280A (ja) * 1996-10-31 1998-05-19 Tosoh Corp アミダーゼ及びそれを用いたピペリジンカルボン酸類の製法
WO1998054308A2 (fr) * 1997-05-28 1998-12-03 Biotica Technology Limited Polycetides, leur synthese et leur utilisation
WO1999007873A1 (fr) * 1997-08-11 1999-02-18 Lonza Ag PROCEDE DE FABRICATION D'α-AMINOACIDES CYCLIQUES EXEMPTS ENANTIOMERES, OU DE LEURS DERIVES N-PROTEGES AU MOYEN D'UNE AMINOACYLASE D-SPECIFIQUE
WO2000020601A2 (fr) * 1998-10-02 2000-04-13 Kosan Biosciences, Inc. Enzymes polyketides synthase et produits d'adn de recombinaisons associes
WO2000023609A1 (fr) * 1998-10-19 2000-04-27 Nsc Technologies Llc Procede de biotransformation de transaminase utilisant un acide glutamique

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0638781A (ja) * 1991-12-11 1994-02-15 Bio-Le Kk １−ピペコリン酸の製造法
JPH0662880A (ja) * 1992-08-10 1994-03-08 Kyowa Hakko Kogyo Co Ltd ４−ヒドロキシ−ｌ−プロリンの製造法
WO1995010604A1 (fr) * 1993-10-15 1995-04-20 Chiroscience Limited Enzyme et son utilisation dans la preparation de l'acide (s) - pipecolique
WO1996001901A1 (fr) * 1994-07-08 1996-01-25 Rhone-Poulenc Rorer S.A. Streptogramines et procede de preparation de streptogramines par mutasynthese
WO1996035775A1 (fr) * 1995-05-08 1996-11-14 Lonza Ag PROCEDE BIOTECHNOLOGIQUE DE PRODUCTION D'ACIDE R-α-CARBOXYLIQUE DE PIPERAZINE ET D'AMIDE D'ACIDE S-α-CARBOXYLIQUE DE PIPERAZINE
JPH10127280A (ja) * 1996-10-31 1998-05-19 Tosoh Corp アミダーゼ及びそれを用いたピペリジンカルボン酸類の製法
WO1998054308A2 (fr) * 1997-05-28 1998-12-03 Biotica Technology Limited Polycetides, leur synthese et leur utilisation
WO1999007873A1 (fr) * 1997-08-11 1999-02-18 Lonza Ag PROCEDE DE FABRICATION D'α-AMINOACIDES CYCLIQUES EXEMPTS ENANTIOMERES, OU DE LEURS DERIVES N-PROTEGES AU MOYEN D'UNE AMINOACYLASE D-SPECIFIQUE
WO2000020601A2 (fr) * 1998-10-02 2000-04-13 Kosan Biosciences, Inc. Enzymes polyketides synthase et produits d'adn de recombinaisons associes
WO2000023609A1 (fr) * 1998-10-19 2000-04-27 Nsc Technologies Llc Procede de biotransformation de transaminase utilisant un acide glutamique

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COSTILOW R N ET AL.: "Ornithine cyclase (deaminating). Purification of a protein that converts ornithine to proline and definition of the optimal assay conditions.", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 246, no. 21, 1971, pages 6655 - 6660, XP008000706, ISSN: 0021-9258 *
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SCHINDLER U ET AL.: "Ornithine cyclodeaminase from octopine Ti plasmid Ach5. Identification, DNA sequence, enzyme properties and comparison with gene and enzyme of nopaline Ti plasmid C58.", JOURNAL OF BACTERIOLOGY, vol. 171, no. 2, 1989, pages 847 - 854, XP001064002, ISSN: 0021-9193 *
STALON V ET AL.: "Catabolism of arginine, citrulline and ornithine by Pseudomonas and related bacteria", JOURNAL OF GENERAL MICROBIOLOGY, vol. 133, no. 9, 1987, pages 2487 - 2496, XP008000767, ISSN: 0022-1287 *
WICKWIRE B M ET AL: "Pipecolic acid biosynthesis in Rhizoctonia leguminicola. 1. The lysine, saccharopine delta-1-piperideine-6-carboxylic acid pathway", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 265, no. 25, 1990, pages 14742 - 14747, XP002190503, ISSN: 0021-9258 *
WILLIAMS D P ET AL.: "Design, synthesis and expression of a human interleukin-2 gene incorporating the codon usage bias found in highly expressed Escherichi coli genes", NUCLEIC ACIDS RESEARCH, vol. 16, no. 22, 25 November 1988 (1988-11-25), pages 10453 - 10467, XP000007466, ISSN: 0305-1048 *
WU K ET AL: "The FK520 gene cluster of Streptomyces hygroscopicus var. ascomyceticus (ATCC 14891) contains genes for biosynthesis of unusual polyketide extender units", GENE, vol. 251, no. 1, June 2000 (2000-06-01), pages 81 - 90, XP004202089, ISSN: 0378-1119 *

Also Published As

Publication number Publication date
CN100482800C (zh) 2009-04-29
CA2449836C (fr) 2012-08-14
FR2825717B1 (fr) 2005-02-18
KR100731597B1 (ko) 2007-06-22
WO2002101003A2 (fr) 2002-12-19
JP2004537296A (ja) 2004-12-16
US20050038255A1 (en) 2005-02-17
AU2002317920A1 (en) 2002-12-23
CA2449836A1 (fr) 2002-12-19
KR20040026660A (ko) 2004-03-31
US7425530B2 (en) 2008-09-16
FR2825717A1 (fr) 2002-12-13
JP3943540B2 (ja) 2007-07-11
CN1529756A (zh) 2004-09-15
EP1409691A2 (fr) 2004-04-21

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