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TOTAL SYNTHESES AND BASIC RESEARCHES OF CIGUATOXIN CONGENERS, AND THEIR APPLICATIONS

Research Project

Project/Area Number 23310146
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

HIRAMA MASAHIRO  東北大学, 理学(系)研究科(研究院), 名誉教授 (10142077)

Co-Investigator(Renkei-kenkyūsha) IKUO Fujii  大阪府立大学, 大学院・理学系研究院, 教授 (70189984)
TSUMURAYA Takeshi  大阪府立大学, 大学院・理学系研究院, 准教授 (00372855)
YAMASHITA Shuji  東北大学, 大学院・理学研究科, 講師 (50419991)
Project Period (FY) 2011-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥19,890,000 (Direct Cost: ¥15,300,000、Indirect Cost: ¥4,590,000)
Fiscal Year 2013: ¥5,720,000 (Direct Cost: ¥4,400,000、Indirect Cost: ¥1,320,000)
Fiscal Year 2012: ¥6,760,000 (Direct Cost: ¥5,200,000、Indirect Cost: ¥1,560,000)
Fiscal Year 2011: ¥7,410,000 (Direct Cost: ¥5,700,000、Indirect Cost: ¥1,710,000)
Keywordsシガトキシン / 抗体 / イムノアッセイ / シガテラ / 中毒予防 / 化学合成 / 全合成 / 毒素 / ナトリウムチャネル
Research Abstract

Ciguatera poisoning is an important medical issue in the tropical and subtropical Pacific and Indian Ocean regions and in the tropical Caribbean. Ciguatoxins, the principal causative agents of ciguatera, are produced by an epiphytic dinoflagellate and transferred to fish through the aquatic food chain. We succeeded in total syntheses of important congeners of ciguatoxins (CTXs), and in this project have successfuly synthesized 54-deoxyCTX1B through our unified convergent strategy. Moreover, synthetic CTX1B was purified and its C13-NMR spectrum has been completely assigned. These accomplishments will contribute to the analysis and identification of the causative CTX congeners in ciguatera poisoning in the world.
Direct sandwich ELISA using anti-CTX monoclonal antibodies prepared by synthetic haptens has been significantly improved to the detection limit of 0.1 pg/mL. This ELISA detection will contribute to the prevention of ciguatera poisoning.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Annual Research Report
  • 2011 Annual Research Report
  • Research Products

    (59 results)

All 2014 2013 2012 2011

All Journal Article (19 results) (of which Peer Reviewed: 19 results,  Open Access: 1 results) Presentation (37 results) Book (2 results) Patent(Industrial Property Rights) (1 results) (of which Overseas: 1 results)

  • [Journal Article] Preparation of Anti-Ciguatoxin Monoclonal Antibodies Using Synthetic Haptens : Sandwich ELISA Detection of Ciguatoxins2014

    • Author(s)
      円 谷健, 藤井郁雄, 平間正博
    • Journal Title

      Journal of AOAC International

      Volume: 97巻 Issue: 2 Pages: 373-379

    • DOI

      10.5740/jaoacint.sgetsumuraya

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Solvent-mediated Tuning of the Regioselectivity of Intramolecular Diaryl Ether Formation : Total Synthesis of (+)-Aspercyclide C2014

    • Author(s)
      吉野達也, 山下修治,佐藤格, 林雄二郎, 平間正博
    • Journal Title

      Chem. Lett

      Volume: 43巻 Issue: 3 Pages: 349-351

    • DOI

      10.1246/cl.131045

    • NAID

      130004868021

    • Related Report
      2013 Annual Research Report 2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] コルチスタチンの全合成2013

    • Author(s)
      山下修治, 平間正博
    • Journal Title

      有機合成化学協会誌

      Volume: 71巻 Pages: 768-778

    • NAID

      10031191014

    • URL

      http://www.ssocj.jp/

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Total Syntheses of Complanadines A and B2013

    • Author(s)
      Le Zhao, 塚野千尋,Eunsang Kwon, 竹本佳司, 平間正博
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 52巻 Issue: 6 Pages: 1722-1725

    • DOI

      10.1002/anie.201208297

    • Related Report
      2013 Final Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Remote C-H Bond Functionalization of Androstane C-Ring : C12-Amination2013

    • Author(s)
      Shuji Yamashita, masafumi Himuro, Yujiro Hayashi, Masahiro Hirama
    • Journal Title

      Tetrahedron Letters

      Volume: 54 Issue: 10 Pages: 1307-1308

    • DOI

      10.1016/j.tetlet.2012.12.103

    • Related Report
      2013 Final Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Synthesis of Zoanthenol ABC-ring by Radical Strategy2013

    • Author(s)
      山下修治, 須田直樹, 林雄二郎, 平間正博
    • Journal Title

      Tetrahedron Lett

      Volume: 54巻 Issue: 11 Pages: 1389-1391

    • DOI

      10.1016/j.tetlet.2012.12.104

    • Related Report
      2013 Final Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Concise Synthesis of the Tetracyclic Framework of Azadiradione: Tandem Radical Cyclization Route2013

    • Author(s)
      山下修治, 成子朗人, 林雄二郎, 平間正博
    • Journal Title

      Chemistry Letters

      Volume: 42 Issue: 3 Pages: 220-221

    • DOI

      10.1246/cl.2013.220

    • NAID

      10031155758

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2013 Final Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] コルチスタチンの全合成2013

    • Author(s)
      山下修治、平間正博
    • Journal Title

      有機合成化学協会誌

      Volume: 71 Pages: 768-778

    • NAID

      10031191014

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper (II) Catalyzed O-Arylation of Tertiary Alcohols with Arylbismuth (III) Reagents : A Vnvenient System for Aryl Transfer2012

    • Author(s)
      原田修治, 林大輔, 佐藤格, 平間正博
    • Journal Title

      Synlett

      Volume: 23巻 Issue: 03 Pages: 405-408

    • DOI

      10.1055/s-0031-1290205

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] The First Total Synthesis of Gravicycle2012

    • Author(s)
      上田克明, 佐藤格, 平間正博
    • Journal Title

      Chemistry Letters

      Volume: 41 Issue: 1 Pages: 87-89

    • DOI

      10.1246/cl.2012.87

    • NAID

      10030222646

    • ISSN
      0366-7022, 1348-0715
    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Development of Monoclonal Antibody Against the Left Wing of Ciguatoxin CTX1B : Thiol Strategy and Sandwich ELISA Detection2012

    • Author(s)
      円谷健, 竹内勝俊, 山下修治, 平間正博, 藤井郁雄
    • Journal Title

      Toxicon

      Volume: 60巻 Issue: 3 Pages: 348-357

    • DOI

      10.1016/j.toxicon.2012.04.347

    • Related Report
      2013 Final Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Aspercyclides A and B via Intramolecular Oxidative Diaryl Ether Formation2012

    • Author(s)
      吉野達也, 佐藤格, 平間正博
    • Journal Title

      Org. Lett

      Volume: 14巻 Issue: 16 Pages: 4290-4292

    • DOI

      10.1021/ol3019727

    • Related Report
      2013 Final Research Report 2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Development of Monoclonal Antibody Against the Left Wing of Ciguatoxin CTX1B : Thiol Strategy and Sandwich ELISA Detection2012

    • Author(s)
      T.Tsumuraya, K.Takeuchi, S.Yamashita, M.Hirama, I.Fujii
    • Journal Title

      Toxicon

      Volume: 60(印刷中)

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The First Total Synthesis of Gravicycle2012

    • Author(s)
      K.Ueda, I.Sato, M.Hirama
    • Journal Title

      Chem.Lett.

      Volume: 41 Pages: 87-89

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper(II) Catalyzed O-Arylation of Tertiary Alcohols with Arylbismuth(III) Reagents : A Convenient System for Aryl Transfer2012

    • Author(s)
      S.Harada, D.Hayashi, I.Sato, M.Hirama
    • Journal Title

      Synlett

      Volume: 23 Pages: 405-408

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Detailed LC-MS/MS Analysis of Ciguatoxins Revealing Distinct Regional and Species Characteristics in Fish and Causative Alga from the Pacific2011

    • Author(s)
      與儀健太郎, 大城直雅, 稲福康夫, 平間正博, 安元健
    • Journal Title

      Anal. Chem

      Volume: 83巻 Issue: 23 Pages: 8886-8891

    • DOI

      10.1021/ac200799j

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Synthesis of the Left Wing of Caribbean Ciguatoxin2011

    • Author(s)
      山下修治, 上松亮平, 平間正博
    • Journal Title

      Tetrahedron

      Volume: 67巻 Issue: 35 Pages: 6616-6626

    • DOI

      10.1016/j.tet.2011.05.080

    • Related Report
      2013 Final Research Report
    • Peer Reviewed
  • [Journal Article] Stereoselective Synthesis of the Left Wing of Caribbean Ciguatoxin2011

    • Author(s)
      S.Yamashita, R.Uematsu, M.Hirama
    • Journal Title

      Tetrahedron

      Volume: 67 Pages: 6616-6626

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Detailed LC-MS/MS Analysis of Ciguatoxins Revealing Distinct Regional and Species Characteristics in Fish and Causative Alga from the Pacific2011

    • Author(s)
      K.Yogi, N.Oshiro, Y.Inafuku, M.Hirama, T.Yasumoto
    • Journal Title

      Anal.Chem.

      Volume: 83 Pages: 8886-8891

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Presentation] 世界最大の海産物中毒と化学のインターフェイス2013

    • Author(s)
      平間正博
    • Organizer
      日本農芸化学会2013年度大会
    • Place of Presentation
      仙台
    • Year and Date
      2013-03-27
    • Related Report
      2013 Final Research Report 2012 Annual Research Report
  • [Presentation] リモニンの全合成研究2013

    • Author(s)
      成子朗人・中澤有紀・山下修治・林雄二郎・平間正博
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津
    • Related Report
      2012 Annual Research Report
  • [Presentation] アンドロスタンC環部の遠隔官能基化法の開発2013

    • Author(s)
      氷室真史・山下修治・林雄二郎・平間正博
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津
    • Related Report
      2012 Annual Research Report
  • [Presentation] プレスポロライドの合成研究2013

    • Author(s)
      寺山香菜江・尾関江理・山下修治・林雄二郎・平間正博
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津
    • Related Report
      2012 Annual Research Report
  • [Presentation] ケダルシジンクロモフォアの全合成研究2013

    • Author(s)
      平井啓一朗・小川幸希・佐藤格・林雄二郎・平間正博
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津
    • Related Report
      2012 Annual Research Report
  • [Presentation] p-ベンザインビラジカルのモノクロロ化反応:2面性とシアノスポラサイドA,Bの合成研究2013

    • Author(s)
      山田慧・山下修治・佐藤格・林雄二郎・平間正博
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津
    • Related Report
      2012 Annual Research Report
  • [Presentation] ウスチロキシンDの全合成研究2013

    • Author(s)
      林大介・原田修治・佐藤格・林雄二郎・平間正博
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津
    • Related Report
      2012 Annual Research Report
  • [Presentation] アスペルサイクライドA,BおよびCの不斉全合成2013

    • Author(s)
      吉野達也・佐藤格・林雄二郎・平間正博
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      草津
    • Related Report
      2012 Annual Research Report
  • [Presentation] プレスポロライドの合成研究(2)2012

    • Author(s)
      寺山香菜江
    • Organizer
      日本化学会第92回春季年会(2012)
    • Place of Presentation
      横浜
    • Related Report
      2011 Annual Research Report
  • [Presentation] アザジラジオンの全合成研究2012

    • Author(s)
      山田孝博
    • Organizer
      日本化学会第92回春季年会(2012)
    • Place of Presentation
      横浜
    • Related Report
      2011 Annual Research Report
  • [Presentation] シアノスポラサイドの全合成研究2012

    • Author(s)
      山田慧
    • Organizer
      日本化学会第92回春季年会(2012)
    • Place of Presentation
      横浜
    • Related Report
      2011 Annual Research Report
  • [Presentation] Ar_3Bi(III)/PhI(OAc)_2をアリール化剤とする3級アルコールの銅触媒O-アリール化の検討2012

    • Author(s)
      林大介
    • Organizer
      日本化学会第92回春季年会(2012)
    • Place of Presentation
      横浜
    • Related Report
      2011 Annual Research Report
  • [Presentation] プレスポロライドの合成研究(1)2012

    • Author(s)
      尾関江理
    • Organizer
      日本化学会第92回春季年会(2012)
    • Place of Presentation
      横浜
    • Related Report
      2011 Annual Research Report
  • [Presentation] アバーメクチンB_<1a>の合成研究2012

    • Author(s)
      仲野葵
    • Organizer
      日本化学会第92回春季年会(2012)
    • Place of Presentation
      横浜
    • Related Report
      2011 Annual Research Report
  • [Presentation] アスペルサイクライド類の全合成研究2012

    • Author(s)
      吉野達也
    • Organizer
      日本化学会第92回春季年会(2012)
    • Place of Presentation
      横浜
    • Related Report
      2011 Annual Research Report
  • [Presentation] コンプラナジン類の全合成研究2012

    • Author(s)
      趙楽
    • Organizer
      日本化学会第92回春季年会(2012)
    • Place of Presentation
      横浜
    • Related Report
      2011 Annual Research Report
  • [Presentation] アザジラクチンAB環部の合成研究2012

    • Author(s)
      務台陽輔
    • Organizer
      日本化学会第92回春季年会(2012)
    • Place of Presentation
      横浜
    • Related Report
      2011 Annual Research Report
  • [Presentation] ラジカル反応を利用したゾアンテノールABC環部の合成研究2012

    • Author(s)
      須田直樹
    • Organizer
      日本化学会第92回春季年会(2012)
    • Place of Presentation
      横浜
    • Related Report
      2011 Annual Research Report
  • [Presentation] ケダルシジンクロモフォアの合成研究2012

    • Author(s)
      平井啓一朗
    • Organizer
      日本化学会第92回春季年会(2012)
    • Place of Presentation
      横浜
    • Related Report
      2011 Annual Research Report
  • [Presentation] リモニンの全合成研究2012

    • Author(s)
      成子朗人
    • Organizer
      日本化学会第92回春季年会(2012)
    • Place of Presentation
      横浜
    • Related Report
      2011 Annual Research Report
  • [Presentation] アザジラクチンCD環部の合成研究2012

    • Author(s)
      氷室真史
    • Organizer
      日本化学会第92回春季年会(2012)
    • Place of Presentation
      横浜
    • Related Report
      2011 Annual Research Report
  • [Presentation] 世界最大の海産物中毒と化学のインターフェイス2011

    • Author(s)
      平間正博
    • Organizer
      大阪府立大学有機化学研究会白鷹セミナー
    • Place of Presentation
      堺
    • Year and Date
      2011-12-13
    • Related Report
      2013 Final Research Report
  • [Presentation] 世界最大の海産物中毒と化学のインターフェイス2011

    • Author(s)
      平間正博
    • Organizer
      大阪府立大学有機化学研究会白鷺セミナー
    • Place of Presentation
      堺(招待講演)
    • Year and Date
      2011-12-13
    • Related Report
      2011 Annual Research Report
  • [Presentation] 最後まで人間味豊かなケミスト西沢麦夫さん-シガトキシン研究-2011

    • Author(s)
      平間正博
    • Organizer
      西澤麦夫先生追悼講演会
    • Place of Presentation
      徳島(招待講演)
    • Year and Date
      2011-11-26
    • Related Report
      2011 Annual Research Report
  • [Presentation] 天然物合成はシガテラを克服できるか2011

    • Author(s)
      平間正博
    • Organizer
      有機合成化学協会講習会
    • Place of Presentation
      東京
    • Year and Date
      2011-11-17
    • Related Report
      2013 Final Research Report
  • [Presentation] 天然物合成はシガテラを克服できるか2011

    • Author(s)
      平間正博
    • Organizer
      有機合成化学協会講習会
    • Place of Presentation
      東京(特別講演)(紫綬褒章受章記念講演)
    • Year and Date
      2011-11-17
    • Related Report
      2011 Annual Research Report
  • [Presentation] 世界最大の海産物中毒と化学のインターフェイス2011

    • Author(s)
      平間正博
    • Organizer
      薬学月例セミナー
    • Place of Presentation
      静岡(特別講演)
    • Year and Date
      2011-10-17
    • Related Report
      2011 Annual Research Report
  • [Presentation] 世界最大の海産物中毒と化学のインターフェイス2011

    • Author(s)
      平間正博
    • Organizer
      東京大学大学院薬学系研究かOrganic Syntheses講演会
    • Place of Presentation
      東京
    • Year and Date
      2011-10-11
    • Related Report
      2013 Final Research Report
  • [Presentation] 世界最大の海産物中毒と化学のインターフェイス2011

    • Author(s)
      平間正博
    • Organizer
      東京大学大学院薬学系研究科"Organic Syntheses"講演会
    • Place of Presentation
      東京(特別講演)
    • Year and Date
      2011-10-11
    • Related Report
      2011 Annual Research Report
  • [Presentation] 抗腫瘍性抗生物質C-1027クロモフォアの全合成研究2011

    • Author(s)
      佐藤格
    • Organizer
      第53回天然有機化合物討論会
    • Place of Presentation
      大阪
    • Year and Date
      2011-09-27
    • Related Report
      2011 Annual Research Report
  • [Presentation] Total Synthesis of Lycodine2011

    • Author(s)
      趙楽
    • Organizer
      G-COE Summer School
    • Place of Presentation
      仙台
    • Year and Date
      2011-08-19
    • Related Report
      2011 Annual Research Report
  • [Presentation] Synthetic Study of C-1027 Chromophore2011

    • Author(s)
      平井啓一朗
    • Organizer
      G-COE Summer School
    • Place of Presentation
      仙台
    • Year and Date
      2011-08-19
    • Related Report
      2011 Annual Research Report
  • [Presentation] Synthetic Studies of Zoanthenol ABC-Ring Based on Radical Reactions2011

    • Author(s)
      須田直樹
    • Organizer
      G-COE Summer School
    • Place of Presentation
      仙台
    • Year and Date
      2011-08-19
    • Related Report
      2011 Annual Research Report
  • [Presentation] Synthesis of CTX1B Left Fragment Utilizing Stereoselective 6-Exo Radical Cyclization and Preparation of Its Hapten Conjugate2011

    • Author(s)
      竹内勝俊
    • Organizer
      G-COE Summer School
    • Place of Presentation
      仙台
    • Year and Date
      2011-08-19
    • Related Report
      2011 Annual Research Report
  • [Presentation] シガテラ中毒への化学の挑戦 : 最近の進歩2011

    • Author(s)
      平間正博
    • Organizer
      理研シンポジウム第6回有機合成化学のフロンティア
    • Place of Presentation
      和光
    • Year and Date
      2011-07-01
    • Related Report
      2013 Final Research Report
  • [Presentation] シガテラ中毒への化学の挑戦:最近の進歩2011

    • Author(s)
      平間正博
    • Organizer
      理研シンポジウム第6回有機合成化学のフロンティア
    • Place of Presentation
      和光(特別講演)
    • Year and Date
      2011-07-01
    • Related Report
      2011 Annual Research Report
  • [Presentation] 有機合成を基盤とする抗シガトキシン抗体の作製と太平洋型シガトキシンの微量検出法の開発2011

    • Author(s)
      円谷健
    • Organizer
      反応と合成の進歩シンポジウム
    • Place of Presentation
      徳島
    • Related Report
      2011 Annual Research Report
  • [Book] 天然物合成で活躍した反応-実験のコツとポイント2011

    • Author(s)
      山下修治, 平間正博, 化学同人
    • Publisher
      有機合成化学協会編
    • Related Report
      2013 Final Research Report
  • [Book] 天然物合成で活躍した反応-実験のコツとポイント、Ni触媒を用いたクロスカップリング、有機合成化学協会編2011

    • Author(s)
      山下修治、平間正博
    • Total Pages
      4
    • Publisher
      化学同人
    • Related Report
      2011 Annual Research Report
  • [Patent(Industrial Property Rights)] シガトキシン類CTX1Bおよび54-デオキシ-CTX1Bを認識するモノクローナル抗体、並びにそれを用いるシガトキシン類検出キット2011

    • Inventor(s)
      藤井郁雄、円谷健、平間正博、山下修治
    • Industrial Property Rights Holder
      公立大学法人大阪府立大学
    • Filing Date
      2011-04-12
    • Related Report
      2011 Annual Research Report
    • Overseas

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Published: 2011-04-06   Modified: 2019-07-29  

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