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Absolute Stereochemistry and Biosynthesis of Antibiotic Enacyloxins.

Research Project

Project/Area Number 09460054
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionTohoku University

Principal Investigator

SUGIYAMA Takeyoshi  Tohoku Univ.Dept.of Applyed Biol.Chem.Associate Professor., 農学部, 助教授 (10125586)

Co-Investigator(Kenkyū-buntansha) WATANABE Toshihiko  Akita Natl.Coll.Technol.Dept.of Chem.Biol.Engineering, Professor., 物質工学科, 教授 (00089799)
Project Period (FY) 1997 – 1998
Project Status Completed (Fiscal Year 1998)
Budget Amount *help
¥10,800,000 (Direct Cost: ¥10,800,000)
Fiscal Year 1998: ¥3,100,000 (Direct Cost: ¥3,100,000)
Fiscal Year 1997: ¥7,700,000 (Direct Cost: ¥7,700,000)
Keywordsenacyloxin / inhibition of protein biosynthesis / antibiotics / absolute stereochemistry / organic synthesis / biosynthesis-related substance / Frateuria sp.W-315
Research Abstract

Enacyloxins (ENXs) are antibiotics produced by bacteria Frateuria sp. W-315 in a spent medium of Neurospora crassa. They are active against Gram-positive and Gram-negative bacteria Their mode of action is considered to be the inhibition of protein biosynthesis of susceptible strains. To elcidate the absolute stereochemistry of EM, ENX IIa derivative was oxidized with periodate and one of the products were compared with authentic samples which were derived from D-glucose. The stereochemistry of some of chiral centers were determined as 12'S, 17'R,18'S,19'R.The stereochemistry of other chiral centers are studied now.
As to biosynthesis of ENX, acidic compound, which appearance and disappearance are closely related to the biosynthetic status of EM, was newly found in the culture medium. To elucidate the chemical structure of the above acidic compound, the production and pufication are in progress.

Report

(3 results)
  • 1998 Annual Research Report   Final Research Report Summary
  • 1997 Annual Research Report
  • Research Products

    (18 results)

All Other

All Publications (18 results)

  • [Publications] Q.-W.Shi: "Three Novel Bicyclic 3,8-Secotaxane Diterpenoids from the Needles of the Chinese Yew, Taxus chinensis var.Mairei." J.Natl.Prod.61. 1437-1440 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Q.-W.Shi: "A Newly Rearranged 2(3→21)Abeotaxane Diterpene from the Bark of Chinese Yew, Taxus mairei." Biosci.Biotechnol.Biochem.62. 2263-2266 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Sassa.: "Acremolactone A, a Herbicidal Epoxydihydropyranyl γ-Lactone from Acremonium roseum 14267." J.Antibibotics. 51. 967-969 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Sassa: "Isolation and Identification of New Antifungal Macrophorins E, F, and G as Malonyl Meroterpenes from Botrysphaeria berengeriana." Biosci.Biotechnol.Biochem.62. 2260-2262 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Q.-W.Shi: "Isolation and Structural Determination of a Novel Bicyclic Taxane Diterpene from Needles of Chinese Yew, Taxus mairei" Biosci.Biotechnol.Biochem.63. 756-759 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Q.-W.Shi: "Thrss Novel Bicyclic 3,8-Secotaxane Diterpenoids from the Needles of Chinese Yew, Taxus chinensis var.mairei." J.Natl.Chem.61. 1437-1440 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Q.-W.Shi: "A Newly Rearranged 2 (3*21) Abeotaxane Diterpene from the Bark of Chinese Yew, Taxus mairei." Biosci.Biotechnol.Biochem.62. 2263-2266 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Sassa: "Acremolactone A,a Herbicidal Epoxydihydroy-pyrannyl eta-lactone from Acremonium roseum 14267." J.Antibiotics. 51. 967-969 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] T.Sassa: "Isolation and Identification of New Antifungal Macrophorins E,F,and G as Malonyl Meroter-penes from Botrysphaeria berengeriana." Biosci.Biotechnol.Biochem.62. 2260-2262 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Q.-W.Shi: "Isolation and Structural Determination of a Novel Bicyclic Taxane Diterpene from Needles from Chinese Yew, Taxus mairei." Biosci.Biotechnol.Biochem.63. 756-759 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1998 Final Research Report Summary
  • [Publications] Q.-W.Shi: "Three Novel Bicyclic 3,8-Secotaxane Diterpenoids from the Needles of the Chinese Tew,Taxus chinensis var.mairei." J.Nati.Prod.61. 1437-1440 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Q.-W.Shi: "A Newly Rearranged 2(3→21)Abeotaxane Diterpene from the Bark of Chinese Yew,Taxus mairei." Biosci.Biotechnol.Biochem.62. 2263-2266 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] T.Sassa: "Acremolactone A,a Herbicidal Epoxydihydropyanyl γ-Lactone from Acremonium roseum 14267." J.Antibiotics. 51. 967-969. (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] T.Sassa: "Isolation and Identification of New Antifungal Macrophorins E,F,and Gas Malony Meroterpenes from Botrysphaeria berengeriana." Biosci.Biotechnol.Biochem.62. 2260-2262 (1998)

    • Related Report
      1998 Annual Research Report
  • [Publications] Q.-W.Shi: "Isolation and Structural Determination of a Novel Bicyclic Taxane Diterpene from Needles of Chinese Yew,Taxus mairei." Biosci.Biotechnol.Biochem.63. 756-759

    • Related Report
      1998 Annual Research Report
  • [Publications] 竹内亮、杉山長美、中山修、折谷隆之、渡辺敏彦: "抗生物質Enacyloxinの立体化学についての研究" 日本農芸化学会誌. 71(3). 120-120 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 竹内嘉房、田中陽光、史清文、杉山長美、山田てい子、折谷隆之: "中国産山椒子(Uvaria purpurea)からの生理活性物質の検索" 日本農芸化学会誌. 71(3). 265-265 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] 竹内亮、杉山長美、折谷隆之、渡辺敏彦: "Enacyloxinの立体化学に関する研究" 日本農芸化学会誌. 72(3). 359-359 (1997)

    • Related Report
      1997 Annual Research Report

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Published: 1997-04-01   Modified: 2016-04-21  

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