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電極電子移動による炭素-炭素結合形成反応に関する研究

Research Project

Project/Area Number 10J07850
Research Category

Grant-in-Aid for JSPS Fellows

Allocation TypeSingle-year Grants
Section国内
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionTokyo University of Agriculture and Technology

Principal Investigator

岡田 洋平  東京農工大学, 連合農学研究科, 特別研究員(PD)

Project Period (FY) 2010 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 2011: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2010: ¥700,000 (Direct Cost: ¥700,000)
Keywords有機電解合成 / 電子 / 酸化還元 / 炭素-炭素結合 / クロスカップリング / ペプチド関連物質 / 立体制御 / 架橋 / 有機電解合成法 / オレフィンクロスカップリング / 架橋構造
Research Abstract

有機電解合成法では反応は電子そのものを試薬とするため,酸化剤や還元剤の添加を必要とせず,反応は非常に穏やかな条件で進行する.本反応系は効率的に炭素-炭素結合を形成する手法として注目を集めており,特にオレフィンカップリングは多様な環化反応を達成するための強力な手法となる.これらの観点から,有機電解合成法はpHや温度に感受性な生体物質への応用が期待される手法となる.本研究では有機電解合成法を用いて穏やかな条件下でペプチド関連物質に架橋構造を導入し,その立体構造を制御することを目的とする.特に[2+2]付加環化反応系をこの目的における研究対象とし,当該年度の研究においては,本反応を反応機構に基づいてその適用範囲の限界を知り,これを踏まえて新たな分子間反応を見出すことに成功した.ペプチド関連物質への応用を視野に入れた新たな反応システムも考案し,分子間反応を効率的に進行させることができた.同時に,ペプチド関連物質への応用を目指した研究にも着手することができ,実際に立体を制約したペプチドの効率的な合成法を確立するに至った.これらの知見は下記に示すように計9件のオリジナル論文ならびに著書として出版され,また国内外の学会で計18件の発表として発信することができた.以上,当該研究で得られた知見ならびに成果は極めて有用であり,今後も発展的に継続していくものであると期待できる.

Report

(2 results)
  • 2011 Annual Research Report
  • 2010 Annual Research Report
  • Research Products

    (48 results)

All 2012 2011 2010

All Journal Article (10 results) (of which Peer Reviewed: 10 results) Presentation (35 results) Book (3 results)

  • [Journal Article] Efficient Intermolecular Carbon-Carbon Bond-Formation Reactions Assisted by Surface-Condensed Electrodes2012

    • Author(s)
      Okada, Y.; Yamaguchi, Y.; Chiba, K.
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2 Issue: 2 Pages: 243-246

    • DOI

      10.1002/ejoc.201101313

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Intermolecular Olefin Cross-Metathesis Initiated by the Umpolung of Enol Ethers2012

    • Author(s)
      Okada, Y.; Chiba, K.
    • Journal Title

      Journal of Synthetic Organic Chemistry Japan

      Volume: (in press)

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cycloalkane-based thermomorphic systems for organic electrochemistry : An application to Kolbe-coupling2012

    • Author(s)
      Okada, Y.; Kamimura, K.; Chiba, K.
    • Journal Title

      Tetrahedron

      Volume: (in press)

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hydrophobic tag-assisted liquid-phase synthesis of a growth hormone-in hibiting peptide somatostatin2011

    • Author(s)
      Kitada, S.; Fujita, S.; Okada, Y.; Kim, S.; Chiba, K.
    • Journal Title

      Bioorganic Medicinal Chemistry Letters

      Volume: 21 Issue: 15 Pages: 4476-4479

    • DOI

      10.1016/j.bmcl.2011.06.004

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Heterogeneous continuous flow synthetic system using cyclohexane-based multiphase electrolyte solutions2011

    • Author(s)
      Okada, Y.; Yoshioka, T.; Koike, M.; Chiba, K.
    • Journal Title

      Tetrahedron Letters

      Volume: 52 Issue: 36 Pages: 4690-4693

    • DOI

      10.1016/j.tetlet.2011.07.007

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Electron transfer-induced four-membered cyclic intermediate formation : Olefin cross-coupling vs.olefin cross-metathesis2011

    • Author(s)
      Okada, Y., Chiba, K.
    • Journal Title

      Electrochim.Acta

      Volume: 56 Pages: 1037-1042

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rate acceleration of Diels-Alder reactions utilizing a fluorous micellar system in water2011

    • Author(s)
      Nishimoto, K., Okada, Y., Kim, S., Chiba, K.
    • Journal Title

      Electrochim.Acta

      Volume: in press

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Electron transfer-induced intermolecular [2+2] cycloaddition reactions based on the aromatic "redox tag" strategy2011

    • Author(s)
      Okada, Y., Nishimoto, A., Akaba, R., Chiba, K.
    • Journal Title

      J.Org.Chem.

      Volume: 76 Pages: 3470-3476

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Continuous electrochemical synthetic system using a multiphase electrolyte solution2010

    • Author(s)
      Okada, Y., Chiba, K.
    • Journal Title

      Electrochim. Acta

      Volume: 55 Pages: 4112-4119

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A practical solution-phase synthesis of an antagonistic peptide of TNF-α based on hydrophobic tag strategy2010

    • Author(s)
      Tana, G., Kitada, S., Fujita, S., Okada, Y., Kim, S., Chiba, K.
    • Journal Title

      Chem.Commun.

      Volume: 46 Pages: 8219-8221

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] 液相二相法を用いた有機電解フロー合成2012

    • Author(s)
      岡田洋平, 小池幹男, 千葉一裕
    • Organizer
      電気化学第79回大会
    • Place of Presentation
      浜松
    • Year and Date
      2012-03-30
    • Related Report
      2011 Annual Research Report
  • [Presentation] 多相電解溶液を用いた効率的分子間炭素-炭素結合形成反応2012

    • Author(s)
      山口勇将, 岡田洋平, 千葉一裕
    • Organizer
      電気化学第79回大会
    • Place of Presentation
      浜松
    • Year and Date
      2012-03-29
    • Related Report
      2011 Annual Research Report
  • [Presentation] シクロアルカン熱応答性多相電解溶液における連続的コルベカップリング2012

    • Author(s)
      上村和也, 岡田洋平, 千葉一裕
    • Organizer
      電気化学第79回大会
    • Place of Presentation
      浜松
    • Year and Date
      2012-03-29
    • Related Report
      2011 Annual Research Report
  • [Presentation] シクロアルカン熱応答性多相電解溶液における連続的コルベカップリング2012

    • Author(s)
      上村和也, 岡田洋平, 千葉一裕
    • Organizer
      日本農芸化学会2012年度大会
    • Place of Presentation
      京都
    • Year and Date
      2012-03-24
    • Related Report
      2011 Annual Research Report
  • [Presentation] 陽極酸化を用いた置換ピロリジンの一段階合成2012

    • Author(s)
      小路貴生, 岡田洋平, 金承鶴, 千葉一裕
    • Organizer
      日本農芸化学会2012年度大会
    • Place of Presentation
      京都
    • Year and Date
      2012-03-24
    • Related Report
      2011 Annual Research Report
  • [Presentation] 液相二相合成法を用いた迅速な一容器ペプチド合成システムの構築2012

    • Author(s)
      小池幹男, 岡田洋平, 千葉一裕
    • Organizer
      日本農芸化学会2012年度大会
    • Place of Presentation
      京都
    • Year and Date
      2012-03-23
    • Related Report
      2011 Annual Research Report
  • [Presentation] 疎水性タグを用いたジスルフィド架橋ペプチドの合成2012

    • Author(s)
      北田慎吾, 藤田秀司, 岡田洋平, 金承鶴, 千葉一裕
    • Organizer
      日本農芸化学会2012年度大会
    • Place of Presentation
      京都
    • Year and Date
      2012-03-23
    • Related Report
      2011 Annual Research Report
  • [Presentation] 疎水性タグを用いた液相ペプチド合成2012

    • Author(s)
      藤田裕子, 格根塔娜, 藤田秀司, 岡田洋平, 金承鶴, 千葉一裕
    • Organizer
      日本農芸化学会2012年度大会
    • Place of Presentation
      京都
    • Year and Date
      2012-03-23
    • Related Report
      2011 Annual Research Report
  • [Presentation] Electron-transfer-induced intermolecular cycloaddition reactions2011

    • Author(s)
      Okada, Y; Kim, S.; Chiba, K.
    • Organizer
      ISOR 10
    • Place of Presentation
      日吉
    • Year and Date
      2011-11-23
    • Related Report
      2011 Annual Research Report
  • [Presentation] Hydrophobic tag-assisted liquid-phase peptide synthesis2011

    • Author(s)
      Chiba, K.; Kim, S.; Okada. Y.; Kitada, S.; Gegen, T.; Fujita, S.
    • Organizer
      ISOR 10
    • Place of Presentation
      日吉
    • Year and Date
      2011-11-22
    • Related Report
      2011 Annual Research Report
  • [Presentation] Practical Intramolecular Disulfide Formation Based on Hydrophobic Tag Strategy2011

    • Author(s)
      Kitada, S.; Fujita, S.; Okada, Y.; Kim, S.; Chiba, K.
    • Organizer
      第48回ペプチド討論会
    • Place of Presentation
      札幌
    • Year and Date
      2011-09-27
    • Related Report
      2011 Annual Research Report
  • [Presentation] Electron Transfer-induced Intermolecular [2+2] Cycloaddition Reactions Based on the Aromatic "Redox Tag" Strategy2011

    • Author(s)
      Okada, Y.; Chiba, K.
    • Organizer
      ISE 62nd Annual Meeting
    • Place of Presentation
      新潟
    • Year and Date
      2011-09-13
    • Related Report
      2011 Annual Research Report
  • [Presentation] Rate acceleration of Diels-Alder reactions utilizing a fluorous micellar system in water2011

    • Author(s)
      Nishimoto, K.; Okada, Y.; Kim, S.; Chiba, K.
    • Organizer
      2011年電気化学秋季大会
    • Place of Presentation
      新潟
    • Year and Date
      2011-09-10
    • Related Report
      2011 Annual Research Report
  • [Presentation] Efficient Intermolecular Carbon-Carbon Bond Formation Reactions Assisted by Surface-condensed Electrodes2011

    • Author(s)
      Yamaguchi, Y.; Okada, Y.; Chiba, K.
    • Organizer
      2011年電気化学秋季大会
    • Place of Presentation
      新潟
    • Year and Date
      2011-09-10
    • Related Report
      2011 Annual Research Report
  • [Presentation] Electron Transfer-induced Intermolecular [2+2] Cycloaddition Reactions Based on the Aromatic "Redox Tag" Strategy2011

    • Author(s)
      Okada, Y.; Nishimoto, A.; Chiba, K.
    • Organizer
      2011年電気化学秋季大会
    • Place of Presentation
      新潟
    • Year and Date
      2011-09-10
    • Related Report
      2011 Annual Research Report
  • [Presentation] Hydrophobic Tag-Assisted Liquid-Phase Synthetic Approach toward Modified Peptides as Medicinal Candidates2011

    • Author(s)
      Okada, Y.; Sugai, M.; Kitada, S.; Gegen, T.; Fujita, S.; Chiba, K.
    • Organizer
      ACS 242nd National Meeting
    • Place of Presentation
      デンバー
    • Year and Date
      2011-08-31
    • Related Report
      2011 Annual Research Report
  • [Presentation] Liquid-Phase N-Functionalized Peptide Synthesis Assisted by Hydrophobic Tag2011

    • Author(s)
      Sugai, M.; Okada, Y.; Gegen, T.; Fujita, S.; Chiba, K.
    • Organizer
      ACS 242nd National Meeting
    • Place of Presentation
      デンバー
    • Year and Date
      2011-08-31
    • Related Report
      2011 Annual Research Report
  • [Presentation] エノールエーテルを基軸とした分子間オレフィンクロスカップリング2011

    • Author(s)
      岡田洋平, 千葉一裕
    • Organizer
      第35回有機電子移動化学討論会
    • Place of Presentation
      福岡
    • Year and Date
      2011-06-23
    • Related Report
      2011 Annual Research Report
  • [Presentation] Electron Transfer-induced Reversible Intermolecular Olefin Cross-coupling Reactions based on "Redox Tag" Strategy2011

    • Author(s)
      Okada, Y.; Chiba, K.
    • Organizer
      ECS 219th Meeting
    • Place of Presentation
      モントリオール
    • Year and Date
      2011-05-02
    • Related Report
      2011 Annual Research Report
  • [Presentation] 液相二相合成法を用いた新規有機電解フロー合成系の構築2011

    • Author(s)
      小池幹男, 岡田洋平, 千葉一裕
    • Organizer
      電気化学第78回大会
    • Place of Presentation
      横浜国立大学
    • Year and Date
      2011-03-31
    • Related Report
      2010 Annual Research Report
  • [Presentation] 不活性オレフィンを基軸とした新規分子間[2+2]付加環化反応2011

    • Author(s)
      西本朝希, 岡田洋平, 千葉一裕
    • Organizer
      電気化学第78回大会
    • Place of Presentation
      横浜国立大学
    • Year and Date
      2011-03-31
    • Related Report
      2010 Annual Research Report
  • [Presentation] 効率的分子間反応を指向した局所反応場の構築2011

    • Author(s)
      山口勇将, 岡田洋平, 千葉一裕
    • Organizer
      電気化学第78回大会
    • Place of Presentation
      横浜国立大学
    • Year and Date
      2011-03-31
    • Related Report
      2010 Annual Research Report
  • [Presentation] 液相二相合成法を用いた新規有機電解フロー合成系の構築2011

    • Author(s)
      小池幹男, 岡田洋平, 千葉一裕
    • Organizer
      日本農芸化学会2011年度大会
    • Place of Presentation
      京都女子大学
    • Year and Date
      2011-03-27
    • Related Report
      2010 Annual Research Report
  • [Presentation] 不活性オレフィンを基軸とした新規分子間[2+2]付加環化反応2011

    • Author(s)
      西本朝希, 岡田洋平, 千葉一裕
    • Organizer
      日本農芸化学会2011年度大会
    • Place of Presentation
      京都女子大学
    • Year and Date
      2011-03-27
    • Related Report
      2010 Annual Research Report
  • [Presentation] 効率的分子間反応を指向した局所反応場の構築2011

    • Author(s)
      山口勇将, 岡田洋平, 千葉一裕
    • Organizer
      日本農芸化学会2011年度大会
    • Place of Presentation
      京都女子大学
    • Year and Date
      2011-03-27
    • Related Report
      2010 Annual Research Report
  • [Presentation] Continuous electrochemical synthetic system using a multiphase electrolyte solution2010

    • Author(s)
      Yohei Okada, Kazuhiro Chiba
    • Organizer
      The International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, America
    • Year and Date
      2010-12-17
    • Related Report
      2010 Annual Research Report
  • [Presentation] Solution-phase peptide synthesis based on hydrophobic tag strategy : facile preparation for bioactive peptide TNF-α2010

    • Author(s)
      Yohei Okada, Gegen Tana, Shingo Kitada, Shuji Fujita, Shokaku Kim, Kazuhiro Chiba
    • Organizer
      5th International Peptide Symposium
    • Place of Presentation
      Kyoto, Japan
    • Year and Date
      2010-12-08
    • Related Report
      2010 Annual Research Report
  • [Presentation] Electron transfer-induced intermolecular olefin cross-coupling reactions2010

    • Author(s)
      Yohei Okada, Kazuhiro Chiba
    • Organizer
      1st German-Japanese Symposium on Eleetrosynthesis
    • Place of Presentation
      Bonn, Germany
    • Year and Date
      2010-10-02
    • Related Report
      2010 Annual Research Report
  • [Presentation] Anodic carbon-carbon bond formation in lithium perchlorate/nitromethane electrolyte solution2010

    • Author(s)
      Kazuhiro Chiba, Yohei Okada, Shokaku Kim
    • Organizer
      1st German-Japanese Symposium on Electrosynthesis
    • Place of Presentation
      Bonn, Germany
    • Year and Date
      2010-10-02
    • Related Report
      2010 Annual Research Report
  • [Presentation] Electran transfer-induced olefin cross-metathesis reactions2010

    • Author(s)
      Yohei Okada, Kazuhiro Chiba
    • Organizer
      ISE 61st Annual Meeting
    • Place of Presentation
      Nice, France
    • Year and Date
      2010-09-30
    • Related Report
      2010 Annual Research Report
  • [Presentation] Electron transfer-induced [2+2] cycloaddition reactions and cycloreversion reactions of cyclobutane ring2010

    • Author(s)
      Yohei Okada, Kazuhiro Chiba
    • Organizer
      ACS 240th Meeting
    • Place of Presentation
      Boston, America
    • Year and Date
      2010-08-25
    • Related Report
      2010 Annual Research Report
  • [Presentation] 四員環遷移状態をモデルとした分子内電子移動の合成化学的検証2010

    • Author(s)
      岡田洋平, 千葉一裕
    • Organizer
      第34回有機電子移動化学討論会
    • Place of Presentation
      大阪府立大学
    • Year and Date
      2010-06-26
    • Related Report
      2010 Annual Research Report
  • [Presentation] 電極電子移動による分子間オレフィンクロスカップリング2010

    • Author(s)
      岡田洋平, 千葉一裕
    • Organizer
      第34回有機電子移動化学討論会
    • Place of Presentation
      大阪府立大学
    • Year and Date
      2010-06-25
    • Related Report
      2010 Annual Research Report
  • [Presentation] Intramolecular electron transfer through non conjugated network probing by the formation of cyclobutane ring2010

    • Author(s)
      Yohei Okada, Ryoichi Akaba, Kazuhiro Chiba
    • Organizer
      ECS 217th meeting
    • Place of Presentation
      Vancouver, Canada
    • Year and Date
      2010-04-26
    • Related Report
      2010 Annual Research Report
  • [Presentation] Long-range electron transfer mediated by carbon-carbon bond formation2010

    • Author(s)
      Ryoichi Akaba, Yohei Okada, Kazuhiro Chiba
    • Organizer
      ECS 217th Meeting
    • Place of Presentation
      Vancouver, Canada
    • Year and Date
      2010-04-26
    • Related Report
      2010 Annual Research Report
  • [Book] Encyclopedia of Applied Electrochemistry2012

    • Author(s)
      Chiba, K.; Okada, Y.
    • Publisher
      Springer(in press)
    • Related Report
      2011 Annual Research Report
  • [Book] Organic Electrochemistry, 5th ed.2012

    • Author(s)
      Chiba, K.; Okada, Y.
    • Publisher
      Taylor & Francis(in press)
    • Related Report
      2011 Annual Research Report
  • [Book] Recent Trend in Electrochemical Science and Technology2011

    • Author(s)
      Chiba, K.; Okada, Y.
    • Total Pages
      16
    • Publisher
      InTech
    • Related Report
      2011 Annual Research Report

URL: 

Published: 2010-12-03   Modified: 2024-03-26  

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