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Stereospecific production of double chiral compounds by novel enzymatic processes

Research Project

Project/Area Number 16380060
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Applied microbiology
Research InstitutionKyoto University

Principal Investigator

KATAOKA Michihiko  Kyoto University, Associate Professor, 農学研究科, 助教授 (90252494)

Co-Investigator(Kenkyū-buntansha) SHIMIZU Sakayu  Kyoto University, Professor, 農学研究科, 教授 (70093250)
OGAWA Jun  Kyoto University, Assistant Professor, 農学研究科, 助手 (70281102)
SAKURADANI Eiji  Kyoto University, Assistant Professor, 農学研究科, 助手 (10362427)
星野 達雄  DSMニュートリショナルプロダクツ(株), 研究顧問
坂本 恵司  第一ファインケミカル(株), 研究部, 基盤技術開発担当部長(研究職)
Project Period (FY) 2004 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥13,700,000 (Direct Cost: ¥13,700,000)
Fiscal Year 2005: ¥4,600,000 (Direct Cost: ¥4,600,000)
Fiscal Year 2004: ¥9,100,000 (Direct Cost: ¥9,100,000)
KeywordsChiral compound / Asymmetric reduction / Old yellow enzyme / Carbonyl reductase
Research Abstract

Chiral compounds are useful intermediates for the production of pharmaceuticals, fine chemicals, and so on. Because of high stereospecificity and environmental aspects, biocatalytic production of chiral compounds has been attracting considerable attention. On the other hand, double chiral compounds, which have two asymmetric carbons in their molecules, are also important for the synthesis of many useful compounds, such as pharmaceuticals and agrochemicals. There are several ways to enzymatically introduce two chiral centers into organic compounds.
Two-step introduction of double chiral centers into the prochiral compound, ketoisophorone, forming (4R,6R)-actinol through two separate enzyme reactions were performed. By combination of old yellow enzyme and levodione reductase, production of doubly chiral compound, (4R,6R)-actinol, which is a useful chiral intermediate for the synthesis of naturally-occurring optically active compounds, such as zeaxanthin and xanthoxin, was investigated. E.coli transformant cells co-expressing old yellow enzyme or levodione reductase gene with cofactor regeneration enzyme gene were used as the catalysts. 100 g/l of ketoisophorone was almost stoichiometrically and stereospecifically converted to (4R,6R)-actinol by two-step reaction Ephedrine is also one of the useful double chiral compounds, and d-ψ-isomer has pharmacological effects as a decongestant or antiasthmatic compound. We found that Rhodococcus erythropolis produces a novel NADP^+-dependent amino alcohol dehydrogenase (AADH), which catalyze the asymmetric reduction of l-isomer in the racemic mixture of the corresponding amino ketone, MAK, to d-ψ-ephedrine. Using E.coli transformant cells coexpressing the genes of AADH and cofactor regeneration enzyme, biocatalytic conversion of racemic MAK to d-ψ-ephedrine by whole cell reaction was performed. Cosequently, 178 mM of d-ψ-ephedrine was formed in 24 h reaction with a molar yield of 89%.

Report

(3 results)
  • 2005 Annual Research Report   Final Research Report Summary
  • 2004 Annual Research Report
  • Research Products

    (22 results)

All 2006 2005 2004

All Journal Article (21 results) Book (1 results)

  • [Journal Article] Gene cloning of an NADPH-dependent menadione reductase from Candida macedoniensis, and its application to chiral alcohol production.2006

    • Author(s)
      Kataoka, M. et al.
    • Journal Title

      Enzyme Microb. Technol. 38

      Pages: 944-951

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A novel NADP^+-dependent L-1-amino-2-propanol dehydrogenase from Rhodococcus erythropolis MAK154 : A promising enzyme for the production of double chiral aminoalcohols.2006

    • Author(s)
      M.Kataoka et al.
    • Journal Title

      Lett. Appl. Microbiol. (in press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Gene cloning of an NADPH-dependent menadione reductase from Candida macedoniensis, and its application to chiral alcohol production.2006

    • Author(s)
      Kataoka, M. et al.
    • Journal Title

      Enzyme Microb.Technol. 38

      Pages: 944-951

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A novel NADP^+-dependent L-1-amino-2-propanol dehydrogenase from Rhodococcus erythropolis MAK154 : A promising enzyme for the production of double chiral aminoalcohols.2006

    • Author(s)
      M.Kataoka, et al.
    • Journal Title

      Lett.Appl.Microbiol. (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Gene cloning of an NADPH-dependent menadione reductase from Candida macedoniensis, and its application to chiral2006

    • Author(s)
      Kataoka, M., et al.
    • Journal Title

      Enzyme Microb.Technol. 38・7

      Pages: 944-951

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Old Yellow Enzymeの再発見:キラルインダストリーへの利用2006

    • Author(s)
      片岡道彦他
    • Journal Title

      バイオサイエンスとインダストリー (印刷中)

    • NAID

      10017483893

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Whole organism biocatalysis.2005

    • Author(s)
      Ishige, T. et al.
    • Journal Title

      Curr. Opin. Chem. Biol. 9(2)

      Pages: 174-180

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Whole organism biocatalysis.2005

    • Author(s)
      Ishige, T. et al.
    • Journal Title

      Curr.Opin.Chem.Biol. 9(2)

      Pages: 174-180

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Screening for Unique Microbial Reactions Useful for Industrial Applications.2005

    • Author(s)
      Ogawa, J. et al.
    • Journal Title

      Handbook of Industrial Biocatalysis (ed. by Ching T.Hou)(Taylor & Francis, Boca Raton)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Whole organism biocatalysis2005

    • Author(s)
      Ishige, T., et al.
    • Journal Title

      Curr.Opin.Chem.Biol. 9・2

      Pages: 174-180

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Expression of the Fusarium oxysporum lactonase gene in Aspergillus oryzae -molecular properties of the2005

    • Author(s)
      Honda, K., et al.
    • Journal Title

      Appl.Microbiol.Biotechnol. 66(5)

      Pages: 520-526

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Practical resolution system for DL-pantoyl lactone using the lactonase from Fusarium oxysporum2005

    • Author(s)
      Sakamoto, K., et al.
    • Journal Title

      J.Biotechnol. 118・1

      Pages: 99-106

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Gene cloning and overexpression of two conjugated polyketone reductases, novel aldo-keto reductase family enzymes, of Candida parapsilosis.2004

    • Author(s)
      Kataoka, M. et al.
    • Journal Title

      Appl. Microbiol. Biotechnol. 64(3)

      Pages: 359-366

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Cloning and overexpression of the old yellow enzyme gene of Candida macedoniensis, and its application to the production of a chiral compound.2004

    • Author(s)
      Kataoka, M. et al.
    • Journal Title

      J. Biotechnol. 114(1-2)

      Pages: 1-9

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Gene cloning and overexpression of two conjugated polyketone reductases, novel aldo-keto reductase family enzymes, of Candida parapsilosis.2004

    • Author(s)
      Kataoka, M. et al.
    • Journal Title

      Appl.Microbiol.Biotechnol. 64(3)

      Pages: 359-366

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Cloning and overexpression of the old yellow enzyme gene of Candida macedoniensis, and its application to the production of a chiral compound.2004

    • Author(s)
      Kataoka, M. et al.
    • Journal Title

      J.Biotechnol. 114(1-2)

      Pages: 1-9

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Cloning and overexpression of the old yellow enzyme gene of Candida macedoniensis, its application to the production of a chiral compound2004

    • Author(s)
      Kataoka, M.et al.
    • Journal Title

      J.Biotechnol. 114・1-2

      Pages: 1-9

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Gene cloning and overexpression of two conjugated polyketone reductases, novel aldo-keto reductase family enzymes, of Candida parapsilosis2004

    • Author(s)
      Kataoka, M.et al.
    • Journal Title

      Appl.Microbiol.Biotechnol. 64・3

      Pages: 359-366

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Biochemical and applied studies of microbial oxidoreductases2004

    • Author(s)
      Delacruz-Hidalgo, A.-R.G.et al.
    • Journal Title

      応用微生物学研究 2・1

      Pages: 39-46

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Expression of the Fusarium oxysporum lactonase gene in Aspergillus oryzae -molecular properties of the recombinant enzyme and its application-.2004

    • Author(s)
      Honda, K.et al.
    • Journal Title

      Appl.Microbiol.Biotechnol. 66・5

      Pages: 520-526

    • Related Report
      2004 Annual Research Report
  • [Journal Article] 有用物質生産のための微生物プロセスの開発に関する基盤的研究2004

    • Author(s)
      清水 昌
    • Journal Title

      農化誌 78・1

      Pages: 4-13

    • NAID

      10013139660

    • Related Report
      2004 Annual Research Report
  • [Book] Handbook of Industrial Biocatalysis(ed. by Ching T. Hou)2005

    • Author(s)
      Ogawa, J. et al.
    • Publisher
      Taylor & Francis, Boca Raton
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary

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Published: 2004-04-01   Modified: 2016-04-21  

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