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2007 Fiscal Year Final Research Report Summary

Microbial production process for stereospecific synthesis of nitrogen-containing chiral compounds

Research Project

Project/Area Number 18380057
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, Grad. Sch. Agriculture, Associate Professor (90252494)

Co-Investigator(Kenkyū-buntansha) SHIMIZU Sakayu  Kyoto University, Grad. Sch, Agriculture, Professor (70093250)
OGAWA Jun  Kyoto University, Grad. Sch, Agriculture, Assistant Professor (70281102)
SAKURADANI Eiji  Kyoto University, Grad. Sch, Agriculture, Assistant Professor (10362427)
HAGISHITA Tairo  Kyoto University, Grad. Sch, Agriculture, Associate Professor (20432346)
HIBI Makoto  Kyoto University, Grad. Sch, Agriculture, Assistant Professor (30432347)
Project Period (FY) 2006 – 2007
Keywordschiral compound / carbonyl reductase / bioreduction / aminoalcohol dehydrogenase / random mutation / Agrobacterium / Rhodococcus
Research Abstract

Chiral compounds are useful intermediates for the production of pharmaceuticals and so on. Because of high stereospecificity and environmental aspects, biocatalytic production of chiral compounds has been attracting considerable attention. On the other hand, nitrogen-containing chiral compounds are also important for the synthesis of many useful compounds, such as pharmaceuticals and agrochemicals.
(1) 3-Quinuclidinone reductase was isolated from Agrobacterium tumefaciens, and characterized in some details. The enzyme belongs to SDR superfamily. Based on amino acid sequence of the enzyme, the gene encoding 3-quinuclidinone reductase was cloned and overexpressed in E. coli transformant cells. Furthermore, E. coli coexpressing 3-quinuclidinone reductase and glucose dehydrogenase genes was constructed, and the production system for (R)-3-quinuclidinol via asymmetric reduction with E. coil transformant cells was established.
(2) Aminoalcohol dehydrogenase from Rhodococcus erythropolis is a promising enzyme for the production of d-pseudoephedrine. However, the enzyme was inhibited by d-pseudoephedrine. To improve aminoalcohol dehydrogenase, a random mutagenesis was performed by error-prone PCR. Finally, several mutant enzymes showing the activity in the presence of high concentration of d-pseudoephedrine. Aminoalcohol dehydrogenase was induced by several aminoalcohols. Through the genetic and transcriptional analysis of aminoalcohol dehydrogenase gene, a homologous orf of the GntR family transcriptional regulators was suggested to be a negative transcriptional regulator of aminoalcohol dehydrogenase gene in R. erythropolis.

  • Research Products

    (15 results)

All 2008 2007 2006

All Journal Article (9 results) (of which Peer Reviewed: 3 results) Presentation (3 results) Book (3 results)

  • [Journal Article] Screening of novel microbial enzymes and their application to chiral compound production2008

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

      Biocatalysis and Bioenergy, John Wiley & Sons (in press)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Microbial enzymes involved in lactone compound metabolism and their biotechnological applications2007

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

      Appl. Microbiol. Biotechnol. 75

      Pages: 257-266

    • Description
      「研究成果報告書概要(和文)」より
    • Peer Reviewed
  • [Journal Article] Microbial enzymes involved in lactone compound metabolism and their biotechnological applications2007

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

      Appl. Microbiol. Biotechnol 75

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Screening of enzymes for regioselective oxidatio and stereoselective reduction2007

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

      Novel Production Technology that uses Microorganism Function-Minimum Genome Factory and System Biology-, CMC Press

      Pages: 138-153

    • Description
      「研究成果報告書概要(欧文)」より
  • [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 aminoalcohols2006

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

      Lett. Appl. Microbiol. 43

      Pages: 430-435

    • Description
      「研究成果報告書概要(和文)」より
    • Peer Reviewed
  • [Journal Article] Gene cloning of an NADPH-dependent menadione reductase from Candida macedoniensis, and its application to chiral alcohol prouction2006

    • 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
    • Peer Reviewed
  • [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 aminoalcohols2006

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

      Lett. Appl. Microbiol 43

      Pages: 430-435

    • Description
      「研究成果報告書概要(欧文)」より
  • [Journal Article] Gene cloning of an NADPH-dependent menadione reductase from Candida macedoniensis, and its application to chiral alcohol production2006

    • Author(s)
      Kataoka, 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
  • [Journal Article] Microbial and enzymatic processes for the production of chiral compounds2006

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

      Biocatalysis in the Pharmaceutical and Biotechnology Industries,(CRC Press)

      Pages: 529-546

    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] Two novel old yellow enzymes catalyzing the asymmetric hydrogenation of C=C bond2007

    • Author(s)
      Kataoka, et. al.
    • Organizer
      Bio Trans2007
    • Place of Presentation
      Oviedo, Spain
    • Year and Date
      20070708-13
    • Description
      「研究成果報告書概要(和文)」より
  • [Presentation] Two novel old yellow enzymes catalyzing the asymmetric hydrogenation of C=C bond2007

    • Author(s)
      Kataoka, et. al.
    • Organizer
      BioTrans2007
    • Place of Presentation
      Oviedo, Spain
    • Year and Date
      20070708-13
    • Description
      「研究成果報告書概要(欧文)」より
  • [Presentation] Production of chiral compounds by microbial enzymes2006

    • Author(s)
      Kataoka and Shimizu
    • Organizer
      International Symposium on Biocatalysis and Bioenergy
    • Place of Presentation
      Taichung, Taiwan
    • Year and Date
      20061206-08
    • Description
      「研究成果報告書概要(和文)」より
  • [Book] Biocatalysis and Bioenergy(分担執筆)2008

    • Author(s)
      Kataoka M., et. al.
    • Publisher
      John Wiley & Sons(印刷中)
    • Description
      「研究成果報告書概要(和文)」より
  • [Book] Biocatalysis in the Pharmaceutical and Biotechnology Industries(分担執筆)2007

    • Author(s)
      Honda K., et. al.
    • Total Pages
      529-546
    • Publisher
      CRC Press
    • Description
      「研究成果報告書概要(和文)」より
  • [Book] 微生物機能を活用した革新的生産技術の最前線-ミニマムゲノムファクトリーとシステムバイオロジ-・(分担執筆)2007

    • Author(s)
      磯部公安, 他
    • Total Pages
      138-153
    • Publisher
      シーエムシー出版
    • Description
      「研究成果報告書概要(和文)」より

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Published: 2010-02-04  

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