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Synthesis and binding sites of new compounds which bind to the sodium channels

Research Project

Project/Area Number 20611002
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical biology
Research InstitutionThe University of Tokyo

Principal Investigator

SATAKE Masayuki  The University of Tokyo, 大学院・理学系研究科, 准教授 (90261495)

Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2010: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2009: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2008: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords環状エーテル / 鈴木カップリング / 渦鞭毛藻 / ナトリウムチャネル / ポリ環状エーテル / 鈴木一宮浦クロスカップリング / 脱保護反応 / 環状エーテル化合物 / 有機化学 / 絶対立体配置
Research Abstract

A polycyclic ether brevisin was isolated from the red tide dinoflagellate Karenia brevis, which produces a variety of polycyclic ethers such as brevetoxins, brevenal, and a mono cyclic ether amide brevisamide. Its unique structure consists of two fused tricyclic ether ring assemblies bridged by a methylene carbon and a conjugated aldehyde side chain, which is similar to brevenal and brevisamide. Its separated polycyclic ether skeleton in the center of the molecule is unusual in the marine polycyclic ethers. Interestingly, even though its skeletal structure is divided into two tricyclic ether units by the methylene, brevisin inhibits the binding of tritiated 42-dihydrobrevetoxin B (PbTx-3) to the voltage sensitive sodium channels (VSSC). In order to confirm its aberrant chemical structure, elucidate its interaction with VSSC, and evaluate its other biological activities, chemical synthesis for its supply was essential. Here the total synthesis of brevisin based on highly convergent strategy using Suzuki-Miyaura cross coupling and aldol reaction as the key reactions was achieved in 29 steps (the longest linear sequence).

Report

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

    (53 results)

All 2011 2010 2009 2008 Other

All Journal Article (16 results) (of which Peer Reviewed: 16 results) Presentation (36 results) Remarks (1 results)

  • [Journal Article] Total Synthesis of (-)-Brevisin : A concise synthesis of a new marine polycyclic ether.2011

    • Author(s)
      T.Kuranaga, N.Ohtani, R.Tsutsumi, D.G.Baden, J.L.C.Wright, M.; Satake, K.Tachibana
    • Journal Title

      Org.Lett. 13

      Pages: 696-699

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of (-)-Brevisin : A Concise Synthesis of a New Marine Polycyclic Ether2011

    • Author(s)
      T.Kuranaga, M.Satake
    • Journal Title

      Organic Letters

      Volume: 13 Pages: 696-699

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Chemoselective deprotection of silyl ethers by DIBALH.2010

    • Author(s)
      T.Kuranaga, S.Ishihara, N.Ohtani, M.Satake, K.Tachibana
    • Journal Title

      Tetrahedron Lett. 51

      Pages: 6345-634

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of the BC/DE ring model of brevisin for confirmation of the structure around the acyclic junction.2010

    • Author(s)
      T.Kuranaga, M.Satake, D.G.Baden, J.L.C.Wright, K.Tachibana
    • Journal Title

      Tetrahedron Lett. 51

      Pages: 4673-4676

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] An improved synthesis of (-)-brevisamide, a marine monocyclic ether amide of dinoflagellate origin.2010

    • Author(s)
      R.Tsutsumi, T.Kuranaga, J.L.C.Wright, D.G.Baden, E.Ito, M.Satake, K.Tachibana
    • Journal Title

      Tetrahedron 66

      Pages: 6775-6782

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of a proposed biosynthetic intermediate of a marine cyclic ether brevisamide for study on biosynthesis of marine ladder-frame polyethers.2010

    • Author(s)
      T.Shirai, T.Kuranaga, D.G.Baden, J.L.C.Wright, M.Satake, K.Tachibana
    • Journal Title

      Tetrahedron Lett. 51

      Pages: 1394-1396

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of the ABC ring fragment of brevisin, a new dinoflagellate polycyclic ether.2010

    • Author(s)
      N.Ohtani, R.Tsutsumi, T.Kuranaga, T.Shirai, D.G.Baden, J.L.C.Wright, M.Satake, K.Tachibana
    • Journal Title

      Heterocycles 80

      Pages: 825-830

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of the ABC ring fragment of brevisin, a new dinoflagellate polycyclic ether.2010

    • Author(s)
      N.Otani, M.Satake
    • Journal Title

      Heterocycles

      Volume: 80 Pages: 825-830

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of a proposed biosynthetic intermediate of a marine cyclic ether brevisamide for study on biosynthesis of marine ladder-frame polyethers2010

    • Author(s)
      T.Shirai, M.Satake
    • Journal Title

      Terahedron Letters

      Volume: 51 Pages: 1394-1396

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] An improved synthesis of (-)-brevisamide, a marine monocyclic ether amide of dinoflagellate origin2010

    • Author(s)
      R.Tsutsumi, M.Satake
    • Journal Title

      Tetrahedron

      Volume: 66 Pages: 6775-6782

    • Related Report
      2010 Annual Research Report Products Report
    • Peer Reviewed
  • [Journal Article] Che, selective deprotection of silyl ethers by DIBALH2010

    • Author(s)
      T.Kuranaga, M.Satake
    • Journal Title

      Tetrahedron Letters

      Volume: 51 Pages: 6345-6348

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of the BC/DE ring model of brevisin for confirmation of the structure around the acyclic junction2010

    • Author(s)
      T.Kuranaga, M.Satake
    • Journal Title

      Tetrahedron Letters

      Volume: 51 Pages: 6345-6348

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of the BC/DE ring model of brevisin for confirmation of the structure around the acyclic junction2010

    • Author(s)
      Kuaranaga, T., Satake, M., Baden DG, Wright, JLC, Tachibana, K.
    • Journal Title

      Tetrahedron Letters

      Volume: 51 Pages: 4673-4676

    • Related Report
      Products Report
    • Peer Reviewed
  • [Journal Article] Synthesis and structural confirmation of brevisamide, a new marine cyclic ether alkaloid from the dinoflagellate Karenia brevis.2009

    • Author(s)
      T.Kuranaga, T.Shirai, J.L.C.Wright, D.G.Baden, M.Satake, K.Tachibana
    • Journal Title

      Org.Lett. 11

      Pages: 217-220

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and structural confirmation of brevisamide, a new marine cyclic ether alkaloid from the dinoflagellate Karenia brevis.2009

    • Author(s)
      T.Kuranaga, M.Satake
    • Journal Title

      Organic Letters

      Volume: 11 Pages: 217-220

    • Related Report
      2009 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total synthesis and structural confirmation of brevisin, a new marine cyclic ether alkaloid from the dinofalgellate Karenia brevis2009

    • Author(s)
      Kuaranaga, T., Shirai, T., Wright, JLC, Baden DG, Satake, M, Tachibana, K.
    • Journal Title

      Organic Letters

      Volume: 11 Pages: 217-220

    • Related Report
      Products Report
    • Peer Reviewed
  • [Presentation] 構造活性相関研究を目指したブレビシン人工類縁体の合成研究2011

    • Author(s)
      石原周二、倉永健史、佐竹真幸、橘和夫
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-28
    • Related Report
      2010 Final Research Report
  • [Presentation] 構造活性相関研究に向けた海産環状エーテル天然物ブレビサミドの類縁体合成2011

    • Author(s)
      荒井博貴、堤亮祐、倉永健史、佐竹真幸、橘和夫
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-28
    • Related Report
      2010 Final Research Report
  • [Presentation] 構造活性相関研究を目指したブレビシン人工類縁体の合成研究2011

    • Author(s)
      石原周二、佐竹真幸
    • Organizer
      日本化学会91春季年会
    • Place of Presentation
      神奈川大学
    • Year and Date
      2011-03-28
    • Related Report
      2010 Annual Research Report
  • [Presentation] DIBALHを用いたシリルエーテルの化学選択的脱保護2011

    • Author(s)
      石原周二、佐竹真幸
    • Organizer
      日本化学会91春季年会
    • Place of Presentation
      神奈川大学
    • Year and Date
      2011-03-28
    • Related Report
      2010 Annual Research Report
  • [Presentation] 構造活性相関研究に向けた海産環状エーテル天然物ブレビサミド類縁体合成2011

    • Author(s)
      荒井博貴、佐竹真幸
    • Organizer
      日本化学会91春季年会
    • Place of Presentation
      神奈川大学
    • Year and Date
      2011-03-28
    • Related Report
      2010 Annual Research Report
  • [Presentation] Total synthesis of brevisin, a new brevetoxin inhibitor2010

    • Author(s)
      T.Kuranaga, M.Satake
    • Organizer
      Pacifichem2010
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2010-12-19
    • Related Report
      2010 Annual Research Report
  • [Presentation] Total synthesis of brevisin, a new brevetoxin inhibitor.2010

    • Author(s)
      Takefumi Kuranaga、Masayuki Satake, et al
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      ヒルトンハワイアンビレッジ、米国ハワイ州
    • Year and Date
      2010-12-19
    • Related Report
      Products Report
  • [Presentation] ポリ環状エーテル天然物の効率的全合成2010

    • Author(s)
      倉永健史、大谷真人、堤亮祐、石原周二、佐竹真幸、Wright JLC、橘和夫
    • Organizer
      ブレビシン第51回天然有機化合物討論会
    • Place of Presentation
      静岡コンベンションツアーセンター
    • Year and Date
      2010-10-01
    • Related Report
      2010 Final Research Report
  • [Presentation] ポリ環状エーテル天然物の効率的全合成、ブレビシン2010

    • Author(s)
      倉永健史、佐竹真幸
    • Organizer
      第51回天然有機化合物討論会
    • Place of Presentation
      静岡コンベンションセンター
    • Year and Date
      2010-10-01
    • Related Report
      2010 Annual Research Report
  • [Presentation] Total SynthesiS of brevisin, a new brevetoxin inhibitor2010

    • Author(s)
      倉永健史、佐竹真幸
    • Organizer
      第9回新規素材探索研究会セミナー
    • Place of Presentation
      横浜ビューホテル
    • Year and Date
      2010-06-11
    • Related Report
      2010 Annual Research Report
  • [Presentation] 渦鞭毛藻由来ポリ環状エーテル天然物ブレビシンABC環部の合成2010

    • Author(s)
      大谷真人、佐竹真幸
    • 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] 新規ポリ環状エーテル天然物ブレビシンの全合成研究2010

    • Author(s)
      倉永健史、佐竹真幸
    • 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] 海産環状エーテルアミド天然物ブレビサミドの改良合成2010

    • Author(s)
      堤亮祐、佐竹真幸
    • 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] DIBAL-Hを用いたシリルエーテルの選択的脱保護2010

    • Author(s)
      石原周二、佐竹真幸
    • 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] ブレベトキシンのナトリウムチャネルへの結合を阻害する新規ポリ環状エーテル天然物ブレビシンの全合成2010

    • Author(s)
      倉永健史、堤亮祐、大谷真人、Wright JLC、佐竹真幸、橘和夫
    • Organizer
      日本ケミカルバイオロジー学会 第5回年会
    • Place of Presentation
      慶応大学
    • Year and Date
      2010-05-18
    • Related Report
      2010 Final Research Report
  • [Presentation] 生物活性解明を目指した海産環状エーテルブレビサミドの合成2010

    • Author(s)
      堤亮祐、倉永健史、白井智大、伊藤恵美子、Wright JLC、佐竹真幸、橘和夫
    • Organizer
      日本ケミカルバイオロジー学会 第5回年会
    • Place of Presentation
      慶応大学
    • Year and Date
      2010-05-18
    • Related Report
      2010 Final Research Report
  • [Presentation] ブレベトキシンのナトリウムチャネルへの結合を阻害する新規ポリ環状エーテル天然物ブレビシンの全合成2010

    • Author(s)
      倉永健史、佐竹真幸
    • Organizer
      日本ケミカルバイオロジー学会第5回年会
    • Place of Presentation
      慶応大学
    • Year and Date
      2010-05-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] 生物活性解明を目指した解散環状エーテルブレビサミドの合成2010

    • Author(s)
      堤亮祐、佐竹真幸
    • Organizer
      日本ケミカルバイオロジー学会第5回年会
    • Place of Presentation
      慶応大学
    • Year and Date
      2010-05-18
    • Related Report
      2010 Annual Research Report
  • [Presentation] 海産環状エーテルアミド ブレビサミドの改良合成2010

    • Author(s)
      堤亮祐、倉永健史、白井智大、Wright JLC、佐竹真幸、橘和夫
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Year and Date
      2010-03-28
    • Related Report
      2010 Final Research Report
  • [Presentation] 海産ポリ環状エーテルブレビシンの合成研究2010

    • Author(s)
      倉永健史、堤亮祐、大谷真人、Wright JLC、佐竹真幸、橘和夫
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Year and Date
      2010-03-28
    • Related Report
      2010 Final Research Report
  • [Presentation] 海産環状エーテルアミドブレビサミドの改良合成2010

    • Author(s)
      堤亮祐、佐竹真幸
    • Organizer
      日本化学会第90回春季年会
    • Place of Presentation
      近畿大学
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] 海産ポリ環状エーテルブレビシンの合成研究2010

    • Author(s)
      倉永健史、佐竹真幸
    • Organizer
      日本化学会第90回春季年会
    • Place of Presentation
      近畿大学
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] 環状エーテルアルカロイドブレビサミドの生合成における推定鎖状前駆体の合成2010

    • Author(s)
      白井智大、佐竹真幸
    • Organizer
      日本化学会第90回春季年会
    • Place of Presentation
      近畿大学
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] Total synthesis of brevisin, a new brevetoxin inhibitor.2010

    • Author(s)
      T.Kuranaga ; N.Ohtani ; R.Tsutsumi ; S.Ishihara ; M.Satake ; J.L.C.Wright ; K.Tachibana
    • Organizer
      Pacifichem 2010
    • Place of Presentation
      Honolulu Hawaii
    • Related Report
      2010 Final Research Report
  • [Presentation] 渦鞭毛藻由来ポリ環状エーテル天然物ブレビシンの非環状メチレンを介した相体立体配置決定を指向した合成研究2009

    • Author(s)
      倉永健史、佐竹真幸、Wright JLC、橘和夫
    • Organizer
      新規素材探索研究会第8回セミナー
    • Place of Presentation
      新横浜フジビューホテル
    • Year and Date
      2009-06-05
    • Related Report
      2010 Final Research Report
  • [Presentation] ポリ環状エーテル化合物の生合成機構解明を目指したブレビサミド推定前駆体の合成2009

    • Author(s)
      白井智大、倉永健史、Wright JLC、佐竹真幸、橘和夫
    • Organizer
      新規素材探索研究会第8回セミナー
    • Place of Presentation
      新横浜フジビューホテル
    • Year and Date
      2009-06-05
    • Related Report
      2010 Final Research Report
  • [Presentation] ポリ環状エーテル化合物の生合成機構解明を目指したブレビサミド推定前駆体の合成2009

    • Author(s)
      白井智大、佐竹真幸
    • Organizer
      新規素材探索研究会第8回セミナー
    • Place of Presentation
      新横浜ビューホテル
    • Year and Date
      2009-06-05
    • Related Report
      2009 Annual Research Report
  • [Presentation] 渦鞭毛藻由来ポリ環状エーテル天然物ブレビシンの非環状メチレンを介した相対立体配置決定を指向した合成研究2009

    • Author(s)
      倉永健史、佐竹真幸
    • Organizer
      新規素材探索研究会第8回セミナー
    • Place of Presentation
      新横浜ビューホテル
    • Year and Date
      2009-06-05
    • Related Report
      2009 Annual Research Report
  • [Presentation] 渦鞭毛藻由来ポリ環状エーテル天然物ブレビシンABC環部の合成研究2009

    • Author(s)
      大谷真人、佐竹真幸
    • Organizer
      第58回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      早稲田大学
    • Year and Date
      2009-05-10
    • Related Report
      2009 Annual Research Report
  • [Presentation] ポリ環状エーテル化合物の生合成機構解明を目指したブレビサミド推定前駆体の合成2009

    • Author(s)
      白井智大、佐竹真幸
    • Organizer
      第58回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      早稲田大学
    • Year and Date
      2009-05-10
    • Related Report
      2009 Annual Research Report
  • [Presentation] 渦鞭毛藻由来ポリ環状エーテル天然物ブレビシンの非環状メチレンを介した相対立体配置決定を指向した合成研究2009

    • Author(s)
      倉永健史、佐竹真幸
    • Organizer
      第58回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      早稲田大学
    • Year and Date
      2009-05-10
    • Related Report
      2009 Annual Research Report
  • [Presentation] 渦鞭毛藻由来環状ポリエーテル天然物ブレビシンABC環部の合成研究2009

    • Author(s)
      大谷真人、堤亮祐、倉永健史、佐竹真幸、Wright JLC、橘和夫
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学理工学部
    • Year and Date
      2009-03-29
    • Related Report
      2010 Final Research Report 2008 Annual Research Report
  • [Presentation] 渦鞭毛藻由来ポリ環状エーテル天然物ブレビシンの非環状メチレンを介した相体立体配置決定を指向した合成研究2009

    • Author(s)
      倉永健史、佐竹真幸、Wright JLC、橘和夫
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学理工学部
    • Year and Date
      2009-03-29
    • Related Report
      2010 Final Research Report 2008 Annual Research Report
  • [Presentation] 環状エーテルアルカロイドブレビサミドの生合成における鎖状前駆体の合成2009

    • Author(s)
      白井智大、倉永健史、Wright JLC、佐竹真幸、橘和夫
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学理工学部
    • Year and Date
      2009-03-29
    • Related Report
      2010 Final Research Report 2008 Annual Research Report
  • [Presentation] ブレビサミドの全合成およびポリ環状エーテル化合物の生合成研究を目指した推定前駆体の合成2009

    • Author(s)
      倉永健史、白井智大、堤亮祐、大谷真人、Wright JLC、佐竹真幸、橘和夫
    • Organizer
      第51回天然有機化合物討論会
    • Place of Presentation
      名古屋市公会堂
    • Related Report
      2010 Final Research Report 2009 Annual Research Report
  • [Presentation] 海産環状エーテル天然物ブレビサミドの構造決定および合成2008

    • Author(s)
      倉永健史、佐竹真幸
    • Organizer
      第7回新規素材探索研究会
    • Place of Presentation
      横浜ビューホテル
    • Year and Date
      2008-06-06
    • Related Report
      2008 Annual Research Report
  • [Remarks] ホームページ等

    • URL

      http://www.chem.s.u-tokyo.ac.jp/users/natural/

    • Related Report
      2010 Final Research Report

URL: 

Published: 2008-04-01   Modified: 2016-09-09  

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