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Total Synthesis of Biologically Active Compounds derived from

Research Project

Project/Area Number 03403024
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionNagoya City University

Principal Investigator

SHIOIRI Takayuki  Nagoya City University, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (20012627)

Project Period (FY) 1991 – 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥34,100,000 (Direct Cost: ¥34,100,000)
Fiscal Year 1993: ¥2,400,000 (Direct Cost: ¥2,400,000)
Fiscal Year 1992: ¥4,100,000 (Direct Cost: ¥4,100,000)
Fiscal Year 1991: ¥27,600,000 (Direct Cost: ¥27,600,000)
Keywordsmarine animal / biologically active compounds / calyculins / theonellamide F / total synthesis / marine sponge / cytotoxicity / stereoselective synthesis
Research Abstract

Recent developments of natural products clemistry have unveiled structures and biological activities of some marine natural products. We have quite interested in their efficient synthesis suitable for the large scale production to investigate their biological profiles in detail. In this research, we have focused our attention to the synthesis of calyculins and theonellamide Fisolated from marine sponges.
The molecule of calyculins was divided into four fragments, three of which were synthesized stereoselectively in an efficient manner. We are now synthesizing the remaining fragment and constructing the whole molecule.
Theonellamide F, a bicyclic dodecapeptide, contains various unusual amino acids. We first synthesized these amino acids, and then accomplished the synthesis of both the southern and northern hemispheres. We are now constructing the whole molecule of theonellamide F from the southern hemisphere.

Report

(4 results)
  • 1993 Annual Research Report   Final Research Report Summary
  • 1992 Annual Research Report
  • 1991 Annual Research Report
  • Research Products

    (23 results)

All Other

All Publications (23 results)

  • [Publications] Keisuke Tohdo: "Synthetic Approach to Theonellamide F" Peptide Chemistry. 1992. 149-151 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Keisuke Tohdo: "Stereoselective Synthesis of (2S,4R)-2-Amino-4-hydroxy-adipic Acid,the Characteristic Amino Acid of Theonellamide F" Synlett. 105-106 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Fumiaki Yokokawa: "Synthesis of the Tetraene Fragment of Calyculins having Natural Configurations" Tetrahedron Letters. 34. 6559-6562 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Tohdo, Keisuke et al: "Synthetic Approach to Thenellamide F" Peptide Chemistry 1992. 149-151 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Tohdo, Keisuke et al: "Stereoselective Synthesis of (2S,4R) -2-Amino-4-hydroxy-adipic Acid, the characteristic Amino Acid of Theonellamide F" Synlett. 105-106 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Yokokawa, Fumiaki et al: "Synthesis of the Tetraene Fragment of Calyculins having Natural Configurations" Tetrahedron Letters. 34. 6559-6562 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Keisuke Tohdo: "Synthetic Approach to Theonellamide F" Peptide Chemistry. 1992. 149-151 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Keisuke Tohdo: "Stereoselective Synthesis of (2S,4R)-2-Amino-4-hydroxyadipic Acid,the Characteristic Amino Acid of Theonellamide F" Synlett. 105-106 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Fumiaki Yokokawa: "Synthesis of the Tetraene Fragment of Calyculins having Natural Configurations" Tetrahedron Letters. 34. 6559-6562 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Keisuke Tohdo: "Theonellamide Fsynthetic studies,Stereoselective synthesis of(3S,4S,5E,7E)-3-amino-8-(4-bromophenyl)-4-hydrvy-6-methyl-5,7-octadienoic aud(ABOA)" Tetrahedron Letters. 33. 2031-2034 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Jun Matsubara: "A synthesis of the tetraene frogment of calyculins as its antipodal form" Tetrahedron Letters. 33. 4187-4190 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Kyoko Hayashi: "Synthesis of nagumamide A,a throbin-ingibitory linear tetrapeptede,from a marine sponge,Theonella.sp." Tetrahedron Letters. 33. 5075-5076 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Fumiaki Yokokawa: "Symthesis of the C_<26>-C_<37> fragment of calyculin A having natural confihuration" Synlett. 703-705 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] 塩入 孝之: "化学で探る海洋生物の謎(化学増刊121号)" 化学同人, 177 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Osamu Hara: "Stereoselectine Synthesis of the C_<13>ーC_<19> Fragment of the Cytotoxic Marine Products Calyculins;Part1" Synlett. 283-284 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Osamu Hara: "Stereoselectire Synthesis of the C_<13>ーC_<19> Fragment of the Cytotoxic Marine Products Calyculins;Part2" Synlett. 285-286 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Yasumasa Hamada: "Stereoselectine Synthesis of 2,3ーDihydroxyー4ーdimethylaminoー5ーmethoxypentanoic Acid,A Fragment of CalyculinsーDetermination of the Absolute Configuration of Calyculins" Tetrahedron Letters. 32. 5983-5986 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Fumiaki.Yokokawa: "A Synthesis of the Oxagole Pant of Calyculins;Part1" Synlett. 149-150 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] Fumiaki.Yokokawa: "A Synthesis of the Oxaqole Part of Calyculins;Part2" Synlett. 151-152 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] Fumiaki.Yokokawa: "Synthesis of 2,4ーDisubstituted Ozaqoles" Synlett. 153-155 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] Keisuke Tohdo: "The onellamide F Synthetic Studies,Stereoselectiue Synthesis of(3S,4S,5E,7E)ー3ーAminoー8ー(4ーdromophenyl)ー4ーhydroxyー6ーmethyl 5,7ーoctadienoic Acid(Aboa)" Tetrahedron Letters. 33. (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] 塩入 孝之 編集: "続医薬品の開発第10巻 海洋資源と医薬品I" 広川書店, 311 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] 塩入 孝之 編集: "続医薬品の開発第10巻 海洋資源と医薬品II" 広川書店, 238 (1992)

    • Related Report
      1991 Annual Research Report

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Published: 1991-04-01   Modified: 2016-04-21  

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