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Chiral syntheses by use of substrate specificities of by use of recombinant prenyltransferases

Research Project

Project/Area Number 12680586
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
Research InstitutionHirosaki University

Principal Investigator

NAGAKI Masahiko  Hirosaki University, Department of Material Science and Technology, Associate Professor, 理工学部, 助教授 (00003533)

Co-Investigator(Kenkyū-buntansha) KOYAMA Tanetoshi  Tohoku University, IMRAM, Professor, 多元物質科学研究所, 教授 (20089808)
Project Period (FY) 2000 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2001: ¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 2000: ¥2,300,000 (Direct Cost: ¥2,300,000)
Keywordschiral synthesis / farnesyl diphospahte synthase / geranyl diphosphate / substrate specificity / prenyltransferase / ndecaprenyl diphosphate / isoprenoid / granylgeranyl diphosphate / ブレニル基転移酵素 / ウンデカプレニル基転移酵素 / イソプレン化学 / 遺伝子組み替え体酵素 / キラル化合物 / キラルシントン / ファルネシルニリン酸合成酵素 / ウンデカプレニルニリン酸合成酵素
Research Abstract

In order to investigate substrate spcificity of Bacillus stearothermophilus farnesyl diphosphate synthase (FPS), we examined the reactivity of 4-alkyl group homologs of isopentenyl diphosphate (IPP).
The enzymatic reactions of the 4-methyl homologs, (E)-3-methylpent-3-enyl diphophate (1a) and (Z)-3methylpent-3-enyl diphophate (Ib) with geranyl diphosphate (GPP) gave 4-methyl-farnesyl diphosphates (2a and 2b), respectively. The stereochemistry of each aldehyde derived from 2a or 2b was determined by CD spectrometry to be (S)- or (R)-4-methylfarnesal, respectively.
Similarly, 1a reacted with dimethylallyl diphosphate (DMAPP) to give a mixture of (4S)-4-methylgeranyl diphospahte (3a) and (4S,8S)-4,8-dimethylfarnesyl diphosphate (4a). The Z-isomer 1b also reacted with DMAPP to give the corresponding enantiomers with (4R)- and (4R,8R)-configurations.
Reactions of the 4-ethyl homologs, (E)--3-methylhex-3-enyl diphosphate (1c) and (Z)-3-methylhex-3enyl diphosphate (1d) with GPP gave two types of … More 4-ethylfarnesyl diphosphates. Reactions of 1c or 1d with DMAPP also gave two types of 4-ethylgeranyl- and 4,8- diethylfarnesyl diphosphates. Meanwhile, reaction of the 4-propyl homologs, (E)--3-methylhept-3-enyl diphosphate (1e) and (Z)-3-methylhept-3-enyl diphosphate (1f) with GPP gave two types of 4-propylfarnesyl diphosphates. Reactions of 1e or 1f with DMAPP gave only two types of the4-propylGPPs
However, neither (E)-3-methyloct-3-enyl diphosphate (1g) or (Z)-3-methyloct-3-enyl diphosphate (1h), nor (E)-4-bromo-3-methylbut-3-enyl diphosphate (1i) or (Z)-4-bromo-3-methylbut-3-enyl diphosphate (1j) was acceptable as a substrate for the thermophilic FPS at all.
On the other hand, in order to investigate the reactivity of the homologs of homoallylic substrates, we examined the enzymatic reactions of (E)-3-methylhex-3-enyl diphosphate or (Z)-3-methylhex-3-enyl diphosphate with FPP using the undecaprenyl diphosphate synthase (UPS) of Micrococcus luteus B-P 26. (E)-3-methylhex-3-enyl diphosphate reacted with FPP to give a chiral (4S)-(2Z,6E,10E,14E)-4-ethyl3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol. However, the Z-isomer is not accepted as a substrate for the bacterial UPS at all. Less

Report

(3 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • Research Products

    (17 results)

All Other

All Publications (17 results)

  • [Publications] 槙 雄二, 長岐正彦, 西野徳三, 古山種俊: "有機合成化学におけるイソプレノイド生合成関連酵素:炭素炭素結合形成ツールとしての有用性と展望"有機合成化学協会誌. (印刷中). (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] 長岐正彦: "Substrate specificity of thermostable farnesyl diphosphate synthase with respect to 4-alkyl homologs of isopentenyl diphosphate"J.Mol.Catal.B : Enzymatic. (in press). (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] 長岐正彦: "Artificial substrates of medium-chain elongating enzymes, hexaprenyl-and heptaprenyl diphosphate synthases"Bioorganic Medicinal Chemistry Letters. 11. 2157-2159 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] 長岐正彦: "Artificial substrate for undecaprenyl diphosphate synthase from Micrococcus luteus B-P 26"Catalysis Communications. 11. 33-35 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] 長岐正彦: "One-pot syntheses of the sex pheromone homologs of a codling moth, Laspeyresia pomonella L."J.Mol.Catal.B : Enzymatic. 10.5. 517-522 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] 長岐正彦: "An artificial substrate for undecaprenyl diphosphate synthase from Micrococcus luteus B-P 26"J.Mol.Catal.B : Enzymatic. 9.1-3. 33-38 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M. Nagaki, S. Sato, Y. Maki, T. Nishino, and T. Koyama: "Artificial Substrates for undecaprenyl diphosphate synthase from Micrococcus luteus B-P 26"J. Mol. Catal., B: Enzymatic.. 9(1-3). 33-38 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M. Nagaki, A. Takaya, Y. Maki, J. Ishibashi, T. Nishino, and T. Koyama: "One-pot syntheses of the sex pheromone homologs of a codling moth, Laspeyresia pomonella L."J. Mol. Catal. B: Enzymatic.. 10 (5). 517-522 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M. Nagaki, S. Sato, Y. Maki, T. Nishino, and T. Koyama: "An artificial substrate for undecaprenyl diphosphate synthase from Micrococcus luteus B-P 26"Catal. Commun.. 1. 33-35 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M. Nagaki, K. Kimura, Y. Maki, T. Nishino, and T. Koyama: "Artificial substrates of medium-chain elongating enzymes, hexaprenyl- and heptaprenyl diphosphate synthases"Bioorg. Med. Chem. Lett.. 11. 2157-2159 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] M. Nagaki, H. Yamamoto, A. Takahashi, Y. Maki, T. Nishino, and T. Koyama: "Substrate specificity of thermostable famesyl diphosphate synthase with respect to 4-alkyl homologs of isopentenyl diphosphate"Bioorg. Med. Chem. Lett.. (in press). (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y. Maki, M. Nagaki, T. Nishino, and T. Koyama: "Usefulness of prenyltransferase for organic synthesis: Carbon-carbon Bond forming reactions by prenyltransferases and their mutated enzymes"Yuki Gosei Kagaku Kyoukaishi. (in press). (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] 長岐 正彦: "Artificial substrates of medium-chain elongating enzymes, hexapreny1-and heptapreny1 diphosphate synthases"Bioorganic Medicinal Chemistry Letters. 11. 2157-2159 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] 長岐 正彦: "An artificial substrate for undecapreny1 diphosphate synthase from Micrococcus Intens B-P 26"Catalysis Communications. 1.1. 33-35 (2000)

    • Related Report
      2001 Annual Research Report
  • [Publications] 長岐 正彦: "One-pot syntheses of the sex pheromone homologs of a codling moth, Laspeyresia pomonella L"J. Mol. Catal. B : Enzymatic. 10.5. 517-522 (2000)

    • Related Report
      2001 Annual Research Report
  • [Publications] 長岐 正彦: "Artificial Substrates for undecapreny1 diphosphate synthase from Micrococcus Inteus B-P 26"J. Mol. Catal. B : Enzymatic. 9.1-3. 33-38 (2000)

    • Related Report
      2001 Annual Research Report
  • [Publications] M.Nagaki,S.Sato,Y.Maki,T.Nishino,and T.Koyama: "An artificial substrate for undecaprenyl diphosphate synthase from Micrococcus luteus B-P 26"Catalysis Communications. 1. 33-35 (2000)

    • Related Report
      2000 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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