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INVESTIGATION ON THE SQUALENE CYCLASE ON THE BASES OF ORGANIC CHEMISTRY AND MOLECULAR BIOLOGY

Research Project

Project/Area Number 11660104
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionNIIGATA UNIVERSITY

Principal Investigator

HOSHINO Tsutomu  DEPARTMENT OF APPLIED BIOLOGICAL CHEMISTRY, FACULTY OF AGRICULTURE, NIIGATA UNIVERSITY, PROFESSOR, 農学部, 教授 (30165542)

Project Period (FY) 1999 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥3,200,000 (Direct Cost: ¥3,200,000)
Fiscal Year 2000: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 1999: ¥2,300,000 (Direct Cost: ¥2,300,000)
Keywordssqualene / oxidosqualene / triterpene / hopene / lanosterol / cyclase / site-directed mutagenesis / Alicyclobacillus acidocaldarius
Research Abstract

This investigation was carried out to gain insight into the squalene cyclization mechanism by using the substrate analogs and by site-directed mutagenesis experiments. We established the initiation site of the cyclization and the stabilization sites as follows. The amino acid alignment of DXDDTA motif, the acidity being enhanced by His 451, is responsible for the initiation and Phe365, Phe601 and Phe605 residues stabilize the cationic intermediates. Incubation experiments of 10-desmethylsqualene analog showed the methyl group at 10-position is most critical to the completion of squalene cyclization.

Report

(3 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • Research Products

    (26 results)

All Other

All Publications (26 results)

  • [Publications] T.Hoshino: "Functional analysis of Phe605, a conserved aromatic amino acid in squalene-hopene cyclases"J.Chem.Soc.Chem.Commun. 1485-1487 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Hoshino: "Unnatural natural triterpenes produced by altering into alanine at position 261 in hopene synthase and the importance of having the appropriate bulk size at this position for directing the stereochemical destiny during the polycyclization cascade"J.Chem.Soc.Chem.Commun. 441-442 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Sato: "Functional analysis of the DXDDTA motif in squalene-hopene cyclase by site-directed mutagenesis experiments : initiation site of the polycyclization reaction and stabilization site of the carbocation intermediate of the initially cyclized A-ring."Biosci.Biotechnol.Biochem.. 63. 2189-2198 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Hoshino: "New cyclization mechanism for squalene : a ring-expansion step for the five-membered C-ring intermediate in hopene biosynthesis"Biosci.Biotechnol.Biochem.. 63. 2038-2041 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Sato: "Functional analysis of phenylalanine 365 in hopene synthase, a conserved amino acid in the families of squalene and oxidosqualene cyclases"J.Chem.Soc.Chem.Commun. 2205-2206 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Hoshino: "The cyclization mechanism of squalene in hopene biosynthesis : the terminal methyl groups are critical to the correct folding of this substrate both for the formation of the five-membered E-ring and for the initiation of the polycyclization reaction"J.Chem.Soc.Chem.Commun.. 731-732 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 星野力: "スクアレン環化酵素:解明されつつある活性部位・触媒機構"バイオサイエンスとインダストリー. 59・3(印刷中). (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Hoshino, M.Kouda, T.Abe and T.Sato.: "Functional analysis of Phe605, a conserved aromatic amino acid in squalene-hopene cyclases"J.Chem.Soc.Chem.Commun.. 1485-1486 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Hoshino, T.Abe and M.Kouda.: "Unnatural natural triterpenes produced by altering into alanine at position 261 in hopene synthase and the importance of having the appropriate bulk size at this position for directing the stereochemical destiny during the polycyclization cascade"J.Chem.Soc.Chem.Commun.. 441-442 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Sato and T.Hoshino.: "Functional analysis of the DXDDTA motif in squalene-hopene cyclase by site-directed mutagenesis experiments : initiation site of the polycyclization reaction and stabilization site of the carbocation intermediate of the initially cyclized A-ring."Biosci.Biotechnol.Biochem.. 63. 2189-2198 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Hoshino, M.Kouda, T.Abe and S.Ohashi.: "New cyclization mechanism for squalene : a ring-expansion step for the five-membered C-ring intermediate in hopene biosynthesis"Biosci.Biotechnol.Biochem.. 63. 2038-2041 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Hoshino and T.Sato.: "Functional analysis of phenylalanine 365 in hopene synthase, a conserved amino acid in the families of squalene and oxidosqualene cyclases"J.Chem.Soc.Chem.Commun.. 2205-2206 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Sato and Hoshino.: "Kinetic studies on the function of all the conserved tryptophans involved inside and outside the QW motifs of squalene-hopene cyclase : stabilizing effect of the protein structure against thermal denaturation"Biosci.Biotechnol.Biochem.. 63. 1171-1180 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Hoshino and K.Kondo.: "The cyclization mechanism of squalene in hopene biosynthesis : the terminal methyl groups are critical to the correct folding of this substrate both for the formation of the five-membered E-ring and for the initiation of the polycyclization reaction"J.Chem.Soc.Chem.Commun.. 731-732 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] T.Hoshino: "Functional analysis of Phe605, a conserved aromatic amino acid in squalene-hopene cyclases"J.Chem.Soc.Chem.Commun. 1485-1487 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Hoshino: "Unnatural natural triterpenes produced by altering into alanine at position 261 in hopene synthase and the importance of having the appropriate bulk size at this position for directing the stereochemical destiny during the polycyclization cascade"J.Chem.Soc.Chem.Commun. 441-442 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Sato: "Functional analysis of the DXDDTA motif in squalene-hopene cyclase by site-directed mutagenesis experiments : initiation site of the polycyclization reaction and stabilization site of the carbocation intermediate of the initially cyclized A-ring."Biosci.Biotechnol.Biochem.. 63. 2189-2198 (1999)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Hoshino: "New cyclization mechanism for squalene : a ring-expansion step for the five-membered C-ring intermediate in hopene biosynthesis"Biosci.Biotechnol.Biochem.. 63. 2038-2041 (1999)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Sato: "Functional analysis of phenylalanine 365 in hopene synthase, a conserved amino acid in the families of squalene and oxidosqualene cyclases"J.Chem.Soc.Chem.Commun. 2205-2206 (1999)

    • Related Report
      2000 Annual Research Report
  • [Publications] T.Hoshino: "The cyclization mechanism of squalene in hopene biosynthesis : the terminal methyl groups are critical to the correct folding of this substrate both for the formation of the five-membered E-ring and for the initiation of the polycyclization reaction."J.Chem.Soc.Chem.Commun.. 731-732 (1999)

    • Related Report
      2000 Annual Research Report
  • [Publications] 星野力: "スクアレン環化酵素:解明されつつある活性部位・触媒機構"バイオサイエンスとインダストリー. 59・3(印刷中). (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] T. Hoshino and T. Kondo: "The cyclization mechanism of squalene in hopene biosynthesis"J. Chem. Soc. Chem. Commun.. 8. 731-732 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T. Sato and T. Hoshino: "Kinetic studies on the function of all the conserved tryptophans involved inside and outside QW motifs….."Biosci. Biotechnol. Biochem. 63. 1171-1180 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T. Hoshino, H. Kouda, T. Abe and S.Ohashi: "New cyclization mechanism for squalene: a ring-expansion…"Biosci. Biotechnol. Biochem.. 63. 2189-2198 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T. Hoshino and T. Sato: "Functional analysis of phenylalanine 365 in hopene synthase"J. Chem. Soc. Chem. Commun.. 21. 2205-2206 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] T. Sato and T. Hoshino: "Functional analysis of the DXDDTA motif in squalene-hopene cyclase by site-directed mutagenesis"Biosci. Biotechnol. Biochem.. 63. 2189-2198 (1999)

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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