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Chemical synethesis of marine cyclic peptides for elucidation of their stereostrutures and biological activities.

Research Project

Project/Area Number 20510204
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Living organism molecular science
Research InstitutionKeio University

Principal Investigator

SUENAGA Kiyotake  Keio University, 理工学部, 准教授 (60273215)

Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
Fiscal Year 2010: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2009: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2008: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords環状ペプチド / 立体構造 / Palau'amide / aurilide / miuraenamide / プロヒビチン / アクチン / 生物活性 / 合成研究 / オーリライド / 環状デプシペプチド / プロヒビチチン / ビセブロモアミド / 構造活性相関 / パラオアミド / ディスコキオライドB / Lyngbya sp. / hexamollamide
Research Abstract

To determine the absolute stereochemistry of palau'amide we synthesized four possible diasteremers of palau'amide with regard to C37 and C38. Among the NMR spectra of the four synthetic diastereomers, that of 1 was identical to that of natural palau'amide. This established the complete stereostructure. SAR study of aurilide was carried out, and target biomolecule of aurilide was determined to be prohibitin in the mitochondria. Synthetic studies on miuraenamide have been carried out. Miuraenamide induces actin polymerization and stabilizes actin filament. In addition, isolation, structure determination, and synthetic studies of related compounds have been carried out.

Report

(4 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (45 results)

All 2011 2010 2009 2008

All Journal Article (15 results) (of which Peer Reviewed: 15 results) Presentation (30 results)

  • [Journal Article] Cell-morphology profiling of a natural product library identifies bisebromoamide and miuraenamide A as actin-filament stabilizers2011

    • Author(s)
      Eriko Sumiya, Hiroki Shimogawa, Hiroaki Sasaki, Masato Tsutsumi, Ken'ichi Yoshita, Makoto Ojika, Kiyotake Suenaga, Motonari Uesugi
    • Journal Title

      ACS Chemical Biology 6(5)

      Pages: 425-431

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Marine Natural Product Aurilide Activates the OPA1-Mediated Apoptosis by Binding to Prohibitin2011

    • Author(s)
      Shin-ichi Sato, Asako Murata, Tsubasa Orihara, Takashi Shirakawa, Kiyotake Suenaga, Hideo Kigoshi, Motonari Uesugi
    • Journal Title

      Chemistry and Biology 18(1)

      Pages: 131-39

    • NAID

      120002807468

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Revised Structure and Structure-Activity Relationship of Bisebromoamide and Structure of Norbisebromoamide from the Marine Cyanobacterium2011

    • Author(s)
      Hiroaki Sasaki, Toshiaki Teruya, Hidesuke Fukazawa, Kiyotake Suenaga
    • Journal Title

      Lyngbya sp.Tetrahedron 67(5)

      Pages: 990-994

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Revised Structure and Structure-Activity Relationship of Bisebromoamide and Structure of Norbisebromoamide from the Marine Cyanobacterium Lyngbya sp.2011

    • Author(s)
      Hiroaki Sasaki, et al.
    • Journal Title

      Tetrahedron

      Volume: 67 Pages: 990-994

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Marine Natural Product Aurilide Activates the OPA1-Mediated Apoptosis by Binding to Prohibitin2011

    • Author(s)
      Shin-ichi Sato, et al.
    • Journal Title

      Chemistry and Biology

      Volume: 18 Pages: 131-139

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cell-morphology profiling of a natural product library identifies bisebromoamide and miuraenamide A as actin-filament stabilizers.2011

    • Author(s)
      Eriko Sumiya, et al
    • Journal Title

      ACS Chemical Biology

      Volume: (掲載決定)

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of palau' amide and its diastereomers : Confirmation of its stereostructure2009

    • Author(s)
      Hirokazu Sugiyama, Atsushi Watanabe, Toshiaki Teruya, Kiyotake Suenaga
    • Journal Title

      Tetrahedron Letters 50(52)

      Pages: 7343-7345

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Bisebromoamide, a Potent Cytotoxic Peptide from the Marine Cyanobacterium Lyngbya sp. : Isolation, Stereostructure, and Biological Activity2009

    • Author(s)
      Toshiaki Teruya, Hiroaki Sasaki, Hidesuke Fukazawa, Kiyotake Suenaga
    • Journal Title

      Organic Letters 11(21)

      Pages: 5062-5065

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Bisebromoamide, a Potent Cytotoxic Peptide from the Marine Cyanobacterium Lyngbyasp.: Isolation, Stereostructure, and Biological Activity2009

    • Author(s)
      Toshiaki Teruya, Hiroaki Sasaki, Hidesuke Fukazawa, Kiyotake Suenaga
    • Journal Title

      Organic Letters 11

      Pages: 5062-5065

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of palau'amide and its diastereomers : Confirmation of its stereostructure2009

    • Author(s)
      Hirokazu Sugiyama, Atsushi Watanabe, Toshiaki Teruya, Kiyotake Suenaga
    • Journal Title

      Tetrahedron Letters 50

      Pages: 7343-7345

    • NAID

      110009757778

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Actin-depolymerizing Compounds2009

    • Author(s)
      Kazuhiro Kitamura, Toshiaki Teruya, Takeshi Kuroda, Hideo Kigoshi, Kiyotake Suenaga
    • Journal Title

      Bioorg. Med. Chem. Lett. 19(7)

      Pages: 1896-1898

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hexamollamide, a Hexapeptide from an Okinawan Ascidian Didemnum molle2008

    • Author(s)
      Toshiaki Teruya, Hiroaki Sasaki, Kiyotake Suenaga
    • Journal Title

      Tetrahedron Letters 49(36)

      Pages: 5297-5299

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Cytotoxicity of Aurilide Analogs2008

    • Author(s)
      Kiyotake Suenaga, Shuri Kajiwara, Satomi Kuribayashi, Tomohisa Handa, Hideo Kigoshi
    • Journal Title

      Bioorganic & Medicinal Chemistry Letters 18(14)

      Pages: 3902-3905

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and Cytotoxicity of Aurilide Analogs.2008

    • Author(s)
      Kiyotake Suenaga, Shuri Kajiwara, Satomi Kuribayashi, Tomohisa Handa, Hideo Kigoshi
    • Journal Title

      Bioorg. Med. Chem. Lett. 18(14)

      Pages: 3902-3905

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hexamollamide, a Hexapeptide from an Okinawan Ascidian Didemnum molle.2008

    • Author(s)
      Toshiaki Teruya, Hiroaki Sasaki, Kiyotake Suenaga
    • Journal Title

      Tetrahedron Lett. 49(36)

      Pages: 5297-5299

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Presentation] 新規鎖状ペプチドBisebromoamide類の合成研究2011

    • Author(s)
      渡邊敦・轟星児・照屋俊明・大野修・末永聖武
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学
    • Year and Date
      2011-03-28
    • Related Report
      2010 Final Research Report
  • [Presentation] 抗菌性デプシペプチド ミウラエナミドAの合成研究2011

    • Author(s)
      徳住啓太・鳥居原英輔・伊藤嘉昌子・照屋俊明・末永聖武
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学
    • Year and Date
      2011-03-28
    • Related Report
      2010 Final Research Report
  • [Presentation] Bisebromoamide, a potent cytotoxic peptide from the marine cyanobacterium Lyngbya sp.2010

    • Author(s)
      Hiroaki Sasaki, Toshiaki Teruya, Kiyotake Suenaga
    • Organizer
      Pachifichem 2010
    • Place of Presentation
      Hawaii
    • Year and Date
      2010-12-19
    • Related Report
      2010 Final Research Report
  • [Presentation] 細胞形態変化誘導活性を指標としたアクチン阻害化合物の探索2010

    • Author(s)
      住谷瑛理子、下川浩輝、佐々木宏明、小鹿一、末永聖武、上杉志成
    • Organizer
      第52回天然有機化合物討論会
    • Place of Presentation
      静岡(講演要旨集)
    • Year and Date
      2010-09-29
    • Related Report
      2010 Final Research Report
  • [Presentation] 海洋産細胞毒性環状デプシペプチドPalau' amideの合成と立体構造2010

    • Author(s)
      渡邊敦、杉山弘和、照屋俊明、大野修、末永聖武
    • Organizer
      第52回天然有機化合物討論会
    • Place of Presentation
      静岡(講演要旨集)
    • Year and Date
      2010-09-29
    • Related Report
      2010 Final Research Report
  • [Presentation] 海洋産細胞毒性環状デプシペプチドPalau'amideの合成と立体構造2010

    • Author(s)
      渡邊敦, ら
    • Organizer
      第52回天然有機化合物討論会
    • Place of Presentation
      静岡グランシップ
    • Year and Date
      2010-09-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] 細胞形態変化誘導活性を指標としたアクチン阻害化合物の探索2010

    • Author(s)
      住谷瑛理子, ら
    • Organizer
      第52回天然有機化合物討論会
    • Place of Presentation
      静岡グランシップ
    • Year and Date
      2010-09-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] 海洋シアノバクテリアLyngbya sp.由来の新規鎖状ペプチドBisebromoamideの単離と構造、生物活性、構造活性相関2010

    • Author(s)
      佐々木宏明・照屋俊明・末永聖武
    • Organizer
      日本化学会第4回関東支部大会
    • Place of Presentation
      筑波大学
    • Year and Date
      2010-08-31
    • Related Report
      2010 Final Research Report
  • [Presentation] 抗菌性デプシペプチドミウラエナミドAの合成研究2010

    • Author(s)
      徳住啓太・鳥居原英輔・照屋俊明・末永聖武
    • Organizer
      日本化学会第4回関東支部大会
    • Place of Presentation
      筑波大学
    • Year and Date
      2010-08-31
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] 新規鎖状ペプチドBisebromoamideの合成研究2010

    • Author(s)
      渡邊敦・轟星児・照屋俊明・大野修・末永聖武
    • Organizer
      日本化学会第4回関東支部大会
    • Place of Presentation
      筑波大学
    • Year and Date
      2010-08-31
    • Related Report
      2010 Final Research Report
  • [Presentation] 新規鎖状ペプチドRisebromoamideの合成研究2010

    • Author(s)
      渡邊敦, ら
    • Organizer
      日本化学会第4回関東支部大会
    • Place of Presentation
      筑波大学
    • Year and Date
      2010-08-31
    • Related Report
      2010 Annual Research Report
  • [Presentation] 海洋シアノバクテリアLyngbya sp.由来の新規鎖状ペプチドBisebromoamideの単離と構造、生物活性、構造活性相関2010

    • Author(s)
      佐々木宏明、照屋俊明、末永聖武
    • Organizer
      新規素材探索研究会第9回セミナー
    • Place of Presentation
      新横浜
    • Year and Date
      2010-06-11
    • Related Report
      2010 Final Research Report
  • [Presentation] 海洋産細胞毒性環状デプシペプチドPalau' amideの合成と立体構造2010

    • Author(s)
      渡邊敦、杉山弘和、照屋俊明、末永聖武
    • Organizer
      第59回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      東京農工大学
    • Year and Date
      2010-05-22
    • Related Report
      2010 Final Research Report
  • [Presentation] 海洋産細胞毒性環状デプシペプチドPalau'amideの合成と立体構造2010

    • Author(s)
      渡邊敦, ら
    • Organizer
      第59回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      東京農工大学
    • Year and Date
      2010-05-22
    • Related Report
      2010 Annual Research Report
  • [Presentation] 海洋天然物Bisebromoamideによるアクチン線維の安定化2010

    • Author(s)
      住谷瑛理子、下川浩輝、佐々木宏明、末永聖武、上杉志成
    • Organizer
      ケミカルバイオロジー学会第5回年会
    • Place of Presentation
      慶應義塾大学
    • Year and Date
      2010-05-19
    • Related Report
      2010 Final Research Report
  • [Presentation] 海洋シアノバクテリアLyngbya sp.由来の新規鎖状ペプチドBisebromoamideの単離と構造、生物活性、構造活性相関2010

    • Author(s)
      佐々木宏明、照屋俊明、末永聖武
    • Organizer
      ケミカルバイオロジー学会第5回年会
    • Place of Presentation
      慶應義塾大学
    • Year and Date
      2010-05-18
    • Related Report
      2010 Final Research Report
  • [Presentation] 抗菌性デプシペプチドミウラエナミドAの合成研究2010

    • Author(s)
      徳住啓太・鳥居原英輔・照屋俊明・末永聖武
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Year and Date
      2010-03-27
    • Related Report
      2010 Final Research Report
  • [Presentation] 新規鎖状ペプチドBisebromoamideの合成研究2010

    • Author(s)
      渡邊敦・轟星児・照屋俊明・末永聖武
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Year and Date
      2010-03-27
    • Related Report
      2010 Final Research Report
  • [Presentation] 海洋産細胞毒性環状デプシペプチドPalau' amideの全合成2010

    • Author(s)
      渡邊敦・杉山弘和・照屋俊明・末永聖武
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Year and Date
      2010-03-27
    • Related Report
      2010 Final Research Report
  • [Presentation] 沖縄産シアノバクテリアLyngbya sp.由来のBisebromoamideの生物活性、構造活性相関2010

    • Author(s)
      佐々木宏明・照屋俊明・末永聖武
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Year and Date
      2010-03-27
    • Related Report
      2010 Final Research Report
  • [Presentation] 沖縄産シアノバクテリアLyngbya sp.由来の新規鎖状ペプチドBisebromoamide の単離と構造2010

    • Author(s)
      佐々木宏明・照屋俊明・末永聖武
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Year and Date
      2010-03-27
    • Related Report
      2010 Final Research Report
  • [Presentation] 海洋産細胞毒性環状デプシペプチド Palau'amide の全合成2010

    • Author(s)
      渡邊敦・杉山弘和・照屋俊明・末永聖武
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Year and Date
      2010-03-27
    • Related Report
      2009 Annual Research Report
  • [Presentation] 沖縄産シアノバクテリアLyngbya sp.由来の新規鎖状ペプチド Bisebromoamideの単離と構造2010

    • Author(s)
      佐々木宏明・照屋俊明・末永聖武
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Year and Date
      2010-03-27
    • Related Report
      2009 Annual Research Report
  • [Presentation] 沖縄産シアノバクテリアLyngbya sp.由来の Bisebromoamide の生物活性、構造活性相関2010

    • Author(s)
      佐々木宏明・照屋俊明・末永聖武
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Year and Date
      2010-03-27
    • Related Report
      2009 Annual Research Report
  • [Presentation] 海洋シアノバクテリア由来の新規鎖状ペプチド及びマクロリド配糖体の単離と絶対立体構造2009

    • Author(s)
      佐々木宏明、北村和大、照屋俊明、末永聖武
    • Organizer
      第51回天然有機化合物討論会
    • Place of Presentation
      名古屋(講演要旨集)
    • Year and Date
      2009-10-07
    • Related Report
      2010 Final Research Report
  • [Presentation] 海洋シアノバクテリア由来の新規鎖状ペプチド及びマクロリド配糖体の単離と絶対立体構造2009

    • Author(s)
      佐々木宏明, 北村和大, 照屋俊明, 末永聖武
    • Organizer
      第51回天然有機化合物討論会
    • Place of Presentation
      名古屋市公会堂
    • Year and Date
      2009-10-07
    • Related Report
      2009 Annual Research Report
  • [Presentation] 海洋産細胞毒性環状デプシペプチドPalau' amide の合成研究2009

    • Author(s)
      杉山弘和・照屋俊明・末永聖武
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学
    • Year and Date
      2009-03-29
    • Related Report
      2010 Final Research Report
  • [Presentation] 抗菌性デプシペプチドMiuraenamide Aの合成研究2009

    • Author(s)
      徳住啓太・鳥居原英輔・照屋俊明・末永聖武
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学
    • Year and Date
      2009-03-29
    • Related Report
      2010 Final Research Report
  • [Presentation] 海洋産細胞毒性環状デプシペプチドPalau'amideの合成研究2009

    • Author(s)
      杉山 弘和, 照屋 俊明, 末永 聖武
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学船橋キャンパス
    • Year and Date
      2009-03-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] 沖縄産ホヤDidemnum molle由来の新規ヘキサペプチドの単離と構造決定2008

    • Author(s)
      佐々木宏明、照屋俊明、末永聖武
    • Organizer
      新規素材探索研究会第7回セミナー
    • Place of Presentation
      新横浜
    • Year and Date
      2008-06-06
    • Related Report
      2010 Final Research Report

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Published: 2008-04-01   Modified: 2016-04-21  

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