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Structure and Enzymatic Reaction Mechanism of Prenyltransferases

Research Project

Project/Area Number 63580111
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 物質生物化学
Research InstitutionTOHOKU UNIVERSITY

Principal Investigator

KOYAMA Tanetoshi  Tohoku University, Chemical Research Institute of Non-Aqueous Solutions, Research Associate, 非水溶液化学研究所, 助手 (20089808)

Project Period (FY) 1988 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 1989: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1988: ¥1,100,000 (Direct Cost: ¥1,100,000)
KeywordsPrenyltransferase / Isoprenoid Biosynthesis / Polyprenol / Farnesyl Diphosphate / Undecaprenyl Diphosphate / Substrate Homologues / Enzyme Mechanism / Substrate Specificity / ファルネシル二リン酸 / ウンデカプレニル二リン酸 / プレニル鎖延長反応 / プレニルトランスフェラーゼ / ポリプレノール / ファルネシルニリン酸シンテターゼ / ウンデカプレニルニリン酸
Research Abstract

1. On Farnesyl Diphosphate Synthase: The enzymatic reactivities of methylenediphosphonate analogues of the substrates of farnesyl diphosphate synthase showed that isopentenyl diphosphate is engaged in the enzymatic reaction as a metal-free form, whereas metal-complexed allylic substrates are the actual forms for the prenyltransferase. Both (S)- and (R)-4- methylfarnesols, Synthesized respectively from (E)- ard (Z)-3-methyl-3-pentenyl diphosphates by means of farnesyl diphosphate synthase reaction, were demonstrated to be of almost 100% enantiomeric purity.
2. On Hexaprenyl Diphosphate Synthase from Micrococcus luteus B-P 26: The catalytic site of hexaprenyl diphosphate synthase is formed by cooperative interaction between the two essential components, A and B, and that cysteine and arginine residues on component B play important roles in the enzymatic activity. Formation of a stable 50-kDa complex of the two essential components of the enzyme, which represents the catalytically active s … More tate of this enzyme, is observed in the presence of inorganic pyrophosphate or one of the substrates, isopentenyl diphosphate br farnesyl diphosphate.
3. On Undecaprenyl Diphosphate Synthase: The synthase reaction with (E)-3-methyl-3-pentenyl diphosphate proceeded in the same stereochemical manner as that with isopentenyl diphosphate, but it had a full stop at the stage where a single condensation of the C_6-homologue with an allylic primer is completed to form a chiral prenyl diphosphate with an extra methyl group at the 4-position. Kinetic experiments with (2Z,6E,10E)-4-methyl-geranylgeranyl diphosphate disclosed the topological capacity of the substrate-binding site of undecaprenyl diphosphate synthase.
4. Polyprenyl Diphosphate Synthase from a Higher Plant: A polyprenyl diphosphate synthase catalyzing the formation of ficaprenyl-type Z,E-mixed polyprenyl diphosphates was partially purified from mulberry leaves, Morus bombysis. The stereochemistry of hydrogen elimination from the 2-position of isopentenyl diphosphate during the Z-prenyl chain formation was determined that the 2-pro-S hydrogen was lost. Less

Report

(3 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • Research Products

    (31 results)

All Other

All Publications (31 results)

  • [Publications] 古山種俊;吉田一郎;小倉協三: "Undecaprenyl Diphosphate Synthase from Micrococcus luteus B-P 26:Essential Factors for the Enzymatic Activity" J.Biochem.103. 867-871 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 古山種俊;国分裕一郎;小倉協三: "Polyprenyl Diphosphate Synthase from Mulberry Leaves:Stereochemistry of Hydrogen Elimination in the Prenyltransferase Reaction" Phytochemistry. 27. 2005-2009 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 古山種俊;伊藤美智夫;大沼信一;小倉協三: "Novel Behavior of Undecaprenyl Diphosphate Synthase toward an Artificial Substrate.Formation of the (S__-)-4-Methyl Derivative of Z__-, E__-,E__--Geranylgeranyl Diphosphate" Tetrahedron Letters. 29. 3807-3810 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 後藤猛;古山種俊;小倉協三: "Different Roles of the Diphosphate Moieties of Allylic and Homoallylic Diphosphates in Prenyltransferase Reaction" Biochem.Biophys.Res.Commun.156. 396-402 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 吉田一郎;古山種俊;小倉協三: "Protection of Hexaprenyl-diphosphate Synthase of Micrococcus luteus B-P 26 against Inactivation by Sulphydryl Reagents and Arginine-specific Reagents" Biochem.Biophys.Acta. 995. 138-143 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 吉田一郎;古山種俊;小倉協三: "Formation of a Stable and Catalytically Active Complex of the Two Essential Components of Hexaprenyl Diphosphate Synthase from Micrococcus luteus B-P 26" Biochem.Biophys.Res.Commun.160. 448-452 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 大沼信一;古山種俊;小倉協三: "The Enantomeric Purity of(S__-)-and(R__-)-4-Methylfarnesols Synthesized from Artificial Substrates by Means of a Farnesyl Diphosphate Synthase Reaction" Bull.Chem.Soc.Jpn.62. 2742-2744 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 大沼信一;古山種俊;小倉協三: "Kinetic Studies on the Prenyl Chain Elongation by Undecaprenyl Diphosphate Synthase with Artificial Substrate Homologues" FEBS Lett.257. 71-74 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 大沼信一;伊藤美智夫;古山種俊;小倉協三: "Undecaprenyl Diphosphate Synth Reaction with Artificial Substrate Homologues--Novel Behavior in the Termination of Prenyl Chain Elongation" Tetrahedron. 45. 6145-6160 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 古山種俊: "バイオ・高分子研究法4 特異な機能を有する微生物とその応用 第5章" 学会出版センタ-, 30 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] T. Koyama, I. Yoshida, and K. Ogura: "Undecaprenyl Diphosphate Synthase from Micrococcus luteus B-P 26: Essential Factors for the Enzymatic Activity." J. Biochem., 103, No.5, 867-871 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] T. Koyama, Y. Kokubun, and K. Ogura: "Polyprenyl Diphosphate Synthase from Mulberry Leaves: Stereochemistry of Hydrogen Elimination in the Prenyltransferase Reaction." Phytochemistry, 27, No.7, 2005-2009 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] T. Koyama, M. Ito, S. Ohnuma, and K. Ogura: "Novel Behavior of Undecaprenyl Diphosphate Synthase toward an Artificial Substrate. Formation of the (S)-4-Methyl Derivatives of Z,E,E-Geranylgeranyl Diphosphate." Tetrahedron Lett., 29, No.31, 3807-3810 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] T. Gotoh, T. Koyama, and K. Ogura: "Different Roles of Diphosphate Moieties of Allylic and Homoallylic Diphosphate in Prenyltransferase Reaction." Biochem. Biophys. Res. Commun., 156, No.1, 396-402 (1988).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] I. Yoshida, T. Koyama, and K. Ogura: "Protection of Hexaprenyldiphosphate Synthase of Micrococcus luteus B-P 26 against Inactivation by Sulphydryl Reagents and Arginine-specific Reagents." Biochim. Biophys. Acta, 995, No.2, 138-143 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] I. Yoshida, T. Koyama, and K. Ogura: "Formation of a Stable and Catalytically Active Complex of the Two Essential Components of Hexaprenyl Diphosphate Synthase from Micrococcus luteus B-P 26." Biochem. Biophys. Res. Commun., 160, No.2, 448-452 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] S. Ohnuma, T. Koyama, and K. Ogura: "The Enantiomeric Purity of (S)- and (R)-4-Methylfarnesols Synthesized from Substrates by Means of a Farnesyl Diphosphate Synthase Reaction." Bull. Chem. Soc. Jpn., 62, No.8, 2742-2744 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] S. Ohnuma, T. Koyama, and K. Ogura: "Kinetic Studies on the Prenyl Chain Elongation by Undecaprenyl Diphosphate Synthase with Artificial Substrate Homologues." FEBS Lett., 257, No.1, 71-74 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] S. Ohnuma, M. Ito, T. Koyama, and K. Ogura: "Undecaprenyl Diphosphate Synthase Reaction with Artificial Substrate Homologues --- Novel Behavior in the Termination of Prenyl Chain Elongation." Tetrahedron, 45, No.19, 6145-6160 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] 吉田一郎,古山種俊,小倉協三: "Protection of Hexaprenyl-diphoshate Synthase of Micrococcus Iuteus B-P 26 against Inactivation by Sulphydryl Reagents and Arginine-Specific Reagents" Biochim.Biophys.Acta. 995. 138-143 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 吉田一郎,古山種俊,小倉協三: "Formation of Stable and Catalytically Active Complex of the Two Essential Components of Hexaprenyl Diphosphate Synthase From Micrococcus 1uteus B-P 26" Biochem.Biophys.Res.Commun.160. 448-452 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 大沼信一,古山種俊,小倉協三: "The Enantiomeric Purity of(S__ー)-and(R__ー)-4-Methylfarnesols Synthesized from Artificial Substrates by Means of a Farnesyl Diphosphate Synthase" Bull.Chem.Soc.Jpn.62. 2742-2744 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 大沼信一,古山種俊,小倉協三: "Kinetic Studies on the Prenyl Chain Elongation by Undecaprenyl Diphosphate Synthase with Artificial Substrate Homologues" FEBS Lett.257. 71-74 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 大沼信一,伊藤美智夫,古山種俊,小倉協三: "Undecaprenyl Diphosphate Synthase Reaction with Artificial Substrate Homologues-Novel Behavior in the Termination of Prenyl Chain Elongation" Tetrahedron. 45. 6145-6160 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 古山種俊: "バイオ・高分子研究法4 特異な機能を有する微生物とその応用 第5章" 学会出版センタ-, 30 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] 古山種俊,吉田一郎,小倉協三: J.Biochem.103. 867-871 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] 古山種俊,国分裕一郎,小倉協三: Phytochemistry. 27. 2005-2009 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] 古山種俊,伊藤美智夫,大沼信一,小倉協三: Tetrahedron Letters. 29. 3807-3810 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] 後藤猛,古山種俊,小倉協三: Biochem.Biophys.Res.Commun.156. 396-402 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] 吉田一郎,古山種俊,小倉協三: Biochem.Biophys.Acta. (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] 古山種俊: "高分子学会バイオ・高分子研究会編「バイオ・高分子研究の進歩」第4巻第5章" 学会出版センター, (1989)

    • Related Report
      1988 Annual Research Report

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Published: 1988-04-01   Modified: 2016-04-21  

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