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New Construction of Biologically Active Substances using Diphenyl Phosphorazidate

Research Project

Project/Area Number 60470151
Research Category

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

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

Principal Investigator

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

Project Period (FY) 1985 – 1986
Project Status Completed (Fiscal Year 1986)
Budget Amount *help
¥4,500,000 (Direct Cost: ¥4,500,000)
Fiscal Year 1986: ¥1,200,000 (Direct Cost: ¥1,200,000)
Fiscal Year 1985: ¥3,300,000 (Direct Cost: ¥3,300,000)
KeywordsPeptide bond formation / Carbon-carbon bond formation / Introduction of amino groups / Cytotoxic cyclic peptides of marine origin / Amino sugars / Anthramycin antibiotics / Diphenyl phosphorazidate / 環化反応
Research Abstract

Diphenyl phosphorazidate (DPPA, <(C_6H_5O)_2> P(O) <N_3> ) is a versatile synthetic reagent. DPPA can be used for (1) the peptide bond formation (N-acylation), (2) the carbon-carbon bond formation (C-acylation), and (3) the introduction of amino functions (amination). By use of these DPPA-mediated reactions as key steps, new construction of biologically active substances has been developed. Several antineoplastic and/or cytotoxic cyclic peptides of marine origin such as dolastatin 3, ascidiacyclamide, patellamides A, B, C, ulithiacyclamide, and ulicyclamide have been prepared using the reaction (1). The C-acylation (2) has been applied to efficient syntheses of L-daunosamine, L-vancosamine, D-ristosamine, and mugineic acid. Tilivalline has been also synthesized through the amination (3) using DPPA.

Report

(1 results)
  • 1986 Final Research Report Summary
  • Research Products

    (18 results)

All Other

All Publications (18 results)

  • [Publications] Yasumasa Hamada: Tetrahedron Letters. 26. 5155-5158 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Yasumasa Hamada: Tetrahedron Letters. 26. 5159-5162 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Yasumasa Hamada: Tetrahedron Letters. 26. 6501-6504 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Shinji Kato: Peptide Chemistry 1985. 67-72 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Shinji Kato: Tetrahedron Letters. 27. 2653-2656 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Shinji Kato: Peptide Chemistry 1986. (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Yasumasa Hamada: Chem.Pharm.Bull.33. 5601-5602 (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Yasumasa Hamada: Journal of Organic Chemistry. 51. 5489-5490 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Shigehiro Mori: Tetrahedron Letters. 27. 6111-6114 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Yasumasa Hamada: "New Methods and Reagents in Organic Synthesis. 55. Total Syntheses of Patellamides B and C, Cytotoxic Cyclic Peptides from a Tunicate 1. Their Proposed Structures should be corrected." Tetrahedron Letters. 26. 5155-5158 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Yasumasa Hamada: "New Methods and Reagents in Organic Synthesis. 56. Total Syntheses of Patellamides B and C, Cytotoxic Cyclic Peptides from a Tunicate 2. Their Real Structures have been determined by their syntheses." Tetrahedron Letters. 26. 5159-5162 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Yasumasa Hamada: "New Methods and Reagents in Organic Synthesis. 58. A Synthesis of Patellamide A, a Cytotoxic Cyclic Peptide from a Tunicate. Revision of Its Proposed Structure" Tetrahedron Letters. 26. 6501-6504 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Shinji Kato: "New Methods and Reagents in Organic Synthesis. 61. Synthetic Studies on Ascidiacyclamide and Ulithiacyclamide, Cytotoxic Cyclic Peptides from Marine Tunicates" Peptide Chemistry 1985. 67-72 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Shinji Kato: "New Methods and Reagents in Organic Synthesis. 64. Total Synthesis of Ulithiacyclamide, a Strong Cytotoxic Cyclic Peptide from Marine Tunicates" Tetrahedron Letters. 27. 2653-2656 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Shinji Kato: "New Methods and Reagents in Organic Synthesis. 70. Synthetic Studies on Ulithiacyclamide and Ulicyclamide, Cytotoxic Cyclic Peptides from Marine Tunicates" Peptide Chemistry 1986. (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Yasumasa Hamada: "New Methods and Reagents in Organic Synthesis. 57. A Stereoselective Synthesis of a Derivative of D-Ristosamine" Chem. Pharm. Bull.33. 5601-5604 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Yasumasa Hamada: "New Methods and Reagents in Organic Synthesis. 63. Synthesis of Mugineic Acid through Direct C-Acylation using Diphenyl Phosphorazidate" J. of Organic Chemistry. 51. 5489-5490 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Shigehiro Mori: "New Methods and Reagents in Organic Synthesis. 65. A Stereoselective Synthesis of Tilivalline" Tetrahedron Letters. 27. 6111-6114 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary

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Published: 1987-03-31   Modified: 2016-04-21  

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