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New Frontier in Bioorganic Chemistry Research

Research Project

Project/Area Number 62303017
Research Category

Grant-in-Aid for Co-operative Research (A)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionKyoto University

Principal Investigator

YONEDA Fumio  Faculty of Pharmaceutical Sciences, Kyoto Univ., 薬学部, 教授 (80040327)

Co-Investigator(Kenkyū-buntansha) FUJII Nobutaka  Faculty of Pharmaceutical Sciences, Kyoto Univ. Professor., 薬学部, 教授 (60109014)
HIROBE Masaaki  Faculty of Pharmaceutical Sciences, Tokyo Univ. Professor., 薬学部, 教授 (20012594)
FUJITA Tetsuro  Faculty of Pharmaceutical Sciences, Kyoto Univ. Professor., 薬学部, 教授 (40027024)
OHTSUKA Eiko  Faculty of Pharmaceutical Sciences, Hokkaido Univ. Professor., 薬学部, 教授 (80028836)
UEDA Tooru  Faculty of Pharmaceutical Sciences, Hokkaido Univ. Professor., 薬学部, 教授 (00001032)
矢島 治明  京都大学, 薬学部, 教授 (00025678)
杉浦 幸雄  京都大学, 化学研究所, 教授 (40025698)
北川 勲  大阪大学, 薬学部, 教授 (20028830)
冨士 薫  京都大学, 化学研究所, 教授 (20027056)
Project Period (FY) 1987 – 1989
Project Status Completed (Fiscal Year 1989)
Budget Amount *help
¥11,400,000 (Direct Cost: ¥11,400,000)
Fiscal Year 1989: ¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1988: ¥4,000,000 (Direct Cost: ¥4,000,000)
Fiscal Year 1987: ¥5,400,000 (Direct Cost: ¥5,400,000)
KeywordsChiral 5-deazaflavin / Retinoid / P-450 model / Modified oligonucleotide / Chiral synthesis / Peptide synthesis / Opioid receptor / Esperamicin / 面不斉5-デアザフラビン / P-450モデル / 修飾オリゴフクレオチド / ペプチヂ合成 / 5-デアザフラビン / ヒトパンクレオスタチン / 核酸 / 蛋白質 / 機能性分子の合成 / 作用機序の解明 / レセプター / 生物有機化学 / 生物活性物質
Research Abstract

New frontiers in bioorganic chemistry focused on nucleic acid, enzyme and bioactive compounds including coenzyme have been developed as follows: 1) Redox coenzyme Factor 420, which was isolated from methane-producing bacteria, has first been synthesized. An axial and planar chiral 5-deazaflavin coenzyme model was designed and synthesized (F. Yoneda). 2) Several oligodeoxyribonucleotides containing 5-modified uracils were synthesized and their interactions with restriction endonuleases were investigated,(T. Ueda). 3) Several oligoribonuleotides have been synthesized using 5'-levulinyl and 2'-tetrahydrofuranyl protection and the phophoramidite approach(E. Ohtsuka). 4) Structure-activity relationships of retinoids were clarified and a new type of retinoidal compounds have been synthesized (K. Shudo). 5) Cytochrome P-450 model system has been constructed and its molecular mechanism has been elucidated (M. Hirobe). 6) Large ring lactone-epoxides possessing ionophore activity were prepared and furthermore naturally occurring ionophores from natural sources have been searched (I. Kitagawa). 7) New reaction mechanism of opioid receptor has been explained using synthetic ligands with active disulfide substituents (K. Kanematsu). 8) Trichosprin-B has been isolated from Trichoderma polysporum and its structure has been determined. The total synthesis also has been achieved (T. Fujita). 9) Several new deprotection methodologies and new disulfide formation reactions have been developed (N. Fum). 10) Synthesis of chiral lactones through addition-elimination process has been realized and its application to indole alkaloids has been achieved (K. Fuji). 11) Nucleotide-specific cleavage and minor-groove interaction of DNA with antitumor antibiotics, bleomycin and esperamicin (Y. Shigiura).

Report

(4 results)
  • 1989 Annual Research Report   Final Research Report Summary
  • 1988 Annual Research Report
  • 1987 Annual Research Report
  • Research Products

    (33 results)

All Other

All Publications (33 results)

  • [Publications] Fumio Yoneda: "Synthesis of Bis(pyridodipyrimidines)an Autorecycling Redox Catalysts and Their Remarkable Turonover in the Oxidation of Alcohols" J.Am.Chem.Soc. 111. 9199-9202 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Tetsuji Kawamoto: "Synthesis and Reaction of a New Type of 5ーDeazaflavin with Axial and Planar Chirality" Tetrahedron Letters. 30. 7431-7434 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Jun Takeda: "Synthesis and Characterization of Novel FlavinーLinked Porphyrins.Mechanism for FlavinーCatalysed Interand Intramolecular 2e/1e ElectronーTransfer Reactions" J.Am.Chem.Soc.109. 7677-7688 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kaour Fuji: "Direct Asymmetric Synthesis of Quaternary Carbon Centers via AdditionーElimination Process:Nitroolefination of αーSubstitueted δーLactones" J.Am.Chem.Soc.111. 7921-7925 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yukio Sugiura: "Nucleotideーspecific Cleavage and Minorーgroove Interaction of DNA with Esperamicin Antitumor Antibiotics" Proc.Natl.Acad.Sci.USA. 86. 7672-7676 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] June Kuwahara: "Sequenceーspecific Recognition and Cleavage of DNA by Metallobleomycin:Minor Groove Binding and Possible Interaction Mode" Proc.Natl.Acad.Sci.USA. 85. 2459-2463 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Fumio Yoneda et al.: "Synthesis of Bis(pyridodipyrimidines) as Autorecycling Redox Catalysts and Their Remarkable Turnover in the Oxidation of Alcohols." J. Am. Chem. Soc.111. 9199-9202 ((1989))

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Jun Takeda et al.: "Synthesis and Characterization of Novel Flavin-Linked Porphyrins. Mechanism for Flavin-Catalysed Inter- and Intramolecular 2e/1e Electron-Transfer Reactions." J. Am. Chem. Soc., 109, 7677-7688 (1987).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Kaoru Fuji et al.: "Direct Asymmetric Synthesis Quaternary Carbon Centers via Addition-Elimination Process: Nitroolefination of alpha-Substituted delta-Lactones." J. Am. Chem. Soc., 111, 7921-7925 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Yukio Sugiura et al.: "Nucleotide-specific Cleavage and Minor-Groove Interaction of DNA with Esperamicin Antitumor Antibiotics." Proc. Natl. Acad. Sci. USA, 86, 7672-7676 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] "Sequence-Specific Recognition and Cleavage of DNA by Metallobleomycin: Minor Groove Binding and Possible Interaction Mode." Proc. Natl. Acad. Aci. USA, 85, 2459-2463 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] "Synthesis and Reaction of a New Type of 5-Deazaflavin with Axial and Planar Chirality" Tetrahedron Letters 30, 7431-7434 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1989 Final Research Report Summary
  • [Publications] Fumio Yoneda: "Synthesis of Bis(pyridodipyrimidines)as Autorecycling Redox Catalysts and Their Remarkable Turnover in the Oxidation of Alcohols" J.Am.Chem.Soc.111. 9199-9202 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Tetsuji Kawamoto: "Synthesis and Characterization of Novel Flavin-Linked Porphyrins.Mechanism for Flavin-Catalyzed Inter- and Intramolecular 2e/le Electron-Transfer Reaxtions" J.Am.Chem.Soc.109. 7677-7688 (1987)

    • Related Report
      1989 Annual Research Report
  • [Publications] Kaoru Fuji: "Direct Asymmetric Synthesis of Quaternary Carbon Centersvia Addition-Elimination Process:Nitroolefination of α-Substituted δ-Lactones" J.Am.Chem.Soc.111. 7921-7925 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] Yukio Sugiura: "Nucleotide-specific cleavage and minor-groove interaction of DNA with Esperamicin antitumor antibiotics" Proc.Natl.Acad.Sci.USA. 86. 7672=767 (1989)

    • Related Report
      1989 Annual Research Report
  • [Publications] June Kuwahara: "Sequence-specific recognition and cleavage of DNA by metallobleomycin: Minor groove binding and possible interaction mode" Proc.Natl.Acad.Sci.USA. 85. 2459-2463 (1988)

    • Related Report
      1989 Annual Research Report
  • [Publications] Xing Chen.: J.Chem.Soc.,Chem.Commun.45 (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] Reiko Yanada.: J.Chem.Soc.,Chem.Commun.238-239 (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] Susumu Funakoshi.: J.Chem.Soc.,Chem.Commun.382-384 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Akira Otaka.: Chem.Pharm.Bull.37. 526-528 (1989)

    • Related Report
      1988 Annual Research Report
  • [Publications] Susumu Funakoshi.: J.Chem.Soc.,Chem.Commun.1588-1590 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] Kiyoshi Tanaka: Tetrahedron. 44. (1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] June Kuwahara: Pro.Natl>acad.Sci.,U.S.A. 86. (1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] Yuichi Hashimoto: Jpn.J.Camcer Res.(Gann). 79. (1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] Kenji Hayakawa: Tetrahedron Letters. 28. 5895-5898 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Isao Kitagawa: Chem.Pharm.Bull.35. 2129-2132 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Jun Takeda: J.Amer.Chem.Soc.109. 7677-7688 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Tetsuro Fujita: J.Antibiotics. 41. (1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] Hideo Inoue: Nucleic Acid Research. 15. 6131-6148 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Akira Ono: Nucleic Acid Research. 15. 3059-3072 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Manabu Node: J.Amer.Chem.Soc.109. 7901-7903 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Nobutaka Fujii: Chem.Pharm.Bull.35. 3447-3452 (1987)

    • Related Report
      1987 Annual Research Report

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Published: 1987-04-01   Modified: 2016-04-21  

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