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Study on precise stereoscopic control method by intramolecular crosslinking of bioactive peptide

Research Project

Project/Area Number 15H04494
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
Research InstitutionTokyo University of Agriculture and Technology

Principal Investigator

Chiba Kazuhiro  東京農工大学, (連合)農学研究科(研究院), 教授 (20227325)

Co-Investigator(Kenkyū-buntansha) 岡田 洋平  東京農工大学, 工学(系)研究科(研究院), 助教 (80749268)
Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥17,160,000 (Direct Cost: ¥13,200,000、Indirect Cost: ¥3,960,000)
Fiscal Year 2017: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2016: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2015: ¥8,190,000 (Direct Cost: ¥6,300,000、Indirect Cost: ¥1,890,000)
Keywordsペプチド / 化学合成 / 立体構造 / 生物活性 / 電解反応 / 架橋 / 非天然型 / 電解合成 / 生体分子 / 合成化学 / 生体材料 / 生物活性物質 / ジスルフィド結合 / 有機化学 / 天然物化学 / 有機電子移動 / 液相合成
Outline of Final Research Achievements

It is essential to develop a new chemical synthesis method that can convert peptide related substances into precisely designed structures including the stereochemistry required for the expression of activity. In this study, a novel peptide molecular cyclization method and intramolecular crosslinking formation control method are established, preconditionally controlled with three or more pairs of crosslinks at arbitrary positions in the molecule, using Conotoxin as a model. In addition, it was aimed to establish a novel chemical synthesis method capable of obtaining a peptide with high purity and high yield. As a result, we developed a new method to relax the rigid structure (conformation) of the chain peptide which interferes with the ring-forming reaction and remove the barrier of intramolecular crosslinking derived from the rigid conformation of the peptide. Based on these results, it was succeeded in developing a precise control method of a new three-dimensional structure.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • Research Products

    (33 results)

All 2018 2017 2016 2015 Other

All Int'l Joint Research (1 results) Journal Article (13 results) (of which Int'l Joint Research: 6 results,  Peer Reviewed: 13 results,  Open Access: 13 results,  Acknowledgement Compliant: 4 results) Presentation (14 results) (of which Int'l Joint Research: 4 results,  Invited: 3 results) Book (3 results) Remarks (2 results)

  • [Int'l Joint Research] Aalto University(Finland)

    • Related Report
      2015 Annual Research Report
  • [Journal Article] A Pot-Economical Liquid Phase PNA Synthesis Enabled by a Soluble Tag-Assisted Method2018

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

      Chemistry Letters

      Volume: 47 Issue: 2 Pages: 138-140

    • DOI

      10.1246/cl.170971

    • NAID

      130006337750

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Observations using Phosphorus-31 Nuclear Magnetic Resonance (31P-NMR) of Structural Changes in Freeze-Thawed Hen Egg Yolk2018

    • Author(s)
      Hiroki Wakamatsu, Akihiro Handa, Kazuhiro Chiba
    • Journal Title

      Food Chemistry

      Volume: 244 Pages: 169-176

    • DOI

      10.1016/j.foodchem.2017.10.032

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Investigating radical cation chain processes in the electrocatalytic Diels-Alder reaction2018

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

      Beilstein Journal of Organic Chemistry

      Volume: 14 Pages: 642-647

    • DOI

      10.3762/bjoc.14.51

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Stepwise radical cation Diels-Alder reaction via multiple pathways2018

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

      Beilstein Journal of Organic Chemistry

      Volume: 14 Pages: 704-708

    • DOI

      10.3762/bjoc.14.59

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Bidirectional Access to Radical Cation Diels-Alder Reactions by Electrocatalysis2017

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

      ChemElectroChem

      Volume: 4 Issue: 8 Pages: 1852-1855

    • DOI

      10.1002/celc.201700286

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Hydrophobic Magnetic Nanoparticle-Assisted One-Pot Liquid Phase Peptide Synthesis2017

    • Author(s)
      Okada, Y.; Asama, H.; Wakamatsu, H.; Chiba, K.; Kamiya, H.
    • Journal Title

      European Journal of Organic Chemistry

      Volume: - Issue: 40 Pages: 5961-5965

    • DOI

      10.1002/ejoc.201700697

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Photo-Triggered Fluorometric Hydrophobic Benzyl Alcohol for Soluble Tag-Assisted Liquid-Phase Peptide Synthesis2017

    • Author(s)
      Wakamatsu, H.; Okada, Y.; Sugai, M.; Hussaini, S. R.; Chiba, K.
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 6 Issue: 11 Pages: 1584-1588

    • DOI

      10.1002/ajoc.201700401

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Physiological effects of a novel artificially synthesized antimalarial cyclic peptide, mahafacyclin B2017

    • Author(s)
      Yuko Fujita, Panpaki Seekaki, Norichika Ogata, Kazuhiro Chiba
    • Journal Title

      PLoS ONE

      Volume: 12 Issue: 11 Pages: 1-12

    • DOI

      10.1371/journal.pone.0188415

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Redox-Tag Processes: Intramolecular Electron Transfer and Its Broad Relationship to Redox Reactions in General2017

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

      Chemical Reviews

      Volume: - Issue: 9 Pages: 1-12

    • DOI

      10.1021/acs.chemrev.7b00400

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Development of anodic modification reaction of N-acryloyl-proline derivatives using lithium pechlrate - nitromethane system2016

    • Author(s)
      Takao Shoji, Suzuna Haraya, Shokaku Kim, Kazuhiro Chiba
    • Journal Title

      Electrochimica Acta

      Volume: 200 Pages: 290-295

    • DOI

      10.1016/j.electacta.2016.03.073

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Hydrophobic benzyl amines as supports for liquid-phase C-terminal amidated peptide synthesis: application to the preparation of ABT-5102015

    • Author(s)
      Emiko Matsumoto, Yuko Fujita, Yohei Okada, Esko I. Kauppinen, Hidehiro Kamiya, Kazuhiro Chiba
    • Journal Title

      J. Peptide Science

      Volume: 21 Issue: 9 Pages: 691-695

    • DOI

      10.1002/psc.2791

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Acid-Triggered Colorimetric Hydrophobic Benzyl Alcohols for Soluble Tag-Assisted Liquid-Phase Synthesis2015

    • Author(s)
      Okada Yohei; Wakamatsu Hiroki; Sugai Masae; Kauppinen Esko; Chiba Kazuhiro
    • Journal Title

      Organic Letters

      Volume: 17 Issue: 17 Pages: 4264-4267

    • DOI

      10.1021/acs.orglett.5b02057

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Functional enhancements of artificial nucleic acids by organic electrolytic synthesis2015

    • Author(s)
      Shoji, Takao; Kim, Shokaku; Chiba, Kazuhiro, Functional enhancements of artificial nucleic acids by organic electrolytic synthesis
    • Journal Title

      Electrochemistry

      Volume: 83 Issue: 4 Pages: 467-471

    • DOI

      10.1021/acs.orglett.6b00077

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Presentation] 水素結合によって誘起されるベンズアルデヒド型蛍光色素2018

    • Author(s)
      岡田 洋平、菅井 正枝、千葉 一裕
    • Organizer
      日本農芸化学会2018年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 蛍光機能をもつ疎水性ベンジルアルコールの開発と液相ペプチド合成への応用2018

    • Author(s)
      森川 栄美、若松 弘起、菅井 正枝、岡田 洋平、千葉 一裕
    • Organizer
      日本農芸化学会2018年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] アザヌクレオシドの立体選択的合成2018

    • Author(s)
      石井 聖華、岡本 一央、千葉 一裕
    • Organizer
      日本農芸化学会2018年度大会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 陽極酸化を用いたアザヌクレオシドの合成2018

    • Author(s)
      岡本一央、石井聖華、小路貴生、千葉一裕
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 過塩素酸リチウム/ニトロメタン系における光励起による環化反応2018

    • Author(s)
      永原神吾、若松弘起、岡田洋平、千葉一裕
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Synthesis of Azanucleosides by Anodic Oxidation in a Lithium Perchlorate--Nitroalkane Electrolyte Solution2017

    • Author(s)
      Kazuhiro Chiba, Takao Shoji, Yohei Okada
    • Organizer
      The 68th Annual Meeting of the International Society of Electrochemistry
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Radical Cation Diels-Alder By Electrocatalyst2017

    • Author(s)
      Yasushi Imada, Kazuhiro Chiba, Yohei Okada
    • Organizer
      231st ECS Meeting
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Efficient Anodic Reactions in Entropic Electrolyte Systems2017

    • Author(s)
      Kazuhiro Chiba
    • Organizer
      German Japanese Symposium on Electrosynthesis 2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 生体分子の間接電解による分子内ジスルフィド結合の形成2016

    • Author(s)
      高橋 優士,川島 里紗,半田 明弘,千葉 一裕
    • Organizer
      電気化学会第83回大会
    • Place of Presentation
      大阪大学(大阪府・吹田市)
    • Year and Date
      2016-03-29
    • Related Report
      2015 Annual Research Report
  • [Presentation] 磁性粒子を用いた効率的液相合成法の開発2016

    • Author(s)
      谷口 大輔、岡田 洋平、北野 克和、千葉 一裕
    • Organizer
      日本農芸化学会2016 年度大会
    • Place of Presentation
      札幌コンベンションセンター、札幌市産業振興センター(北海道・札幌市)
    • Year and Date
      2016-03-28
    • Related Report
      2015 Annual Research Report
  • [Presentation] Anodic approach toward intermolecular carbon-carbon bond formations in lithium perchlorate/nitromethane electrolyte solution2015

    • Author(s)
      Yohei Okada, Kazuhiro Chiba
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu, USA
    • Year and Date
      2015-12-17
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 陽極酸化反応を用いたN-アクリロイルプロリン誘導体の新規修飾法の開発2015

    • Author(s)
      原谷 涼奈,小路 貴生,金 承鶴,千葉 一裕
    • Organizer
      2015年電気化学秋季大会
    • Place of Presentation
      埼玉工業大学(埼玉県・深谷市)
    • Year and Date
      2015-09-11
    • Related Report
      2015 Annual Research Report
  • [Presentation] 電子豊富オレフィンを基軸とした電解炭素-炭素結合形成反応の開発2015

    • Author(s)
      山口 勇将,岡田 洋平,千葉 一裕
    • Organizer
      2015年電気化学秋季大会
    • Place of Presentation
      埼玉工業大学(埼玉県・深谷市)
    • Year and Date
      2015-09-11
    • Related Report
      2015 Annual Research Report
  • [Presentation] 電解反応を用いたラジカルカチオンディールスアルダー反応 の反応機構解析2015

    • Author(s)
      尾﨑 惇史,山口勇将、岡田洋平、千葉一裕
    • Organizer
      第39回有機電子移動化学討論会
    • Place of Presentation
      長崎大学(長崎県・長崎市)
    • Year and Date
      2015-06-25
    • Related Report
      2015 Annual Research Report
  • [Book] 中分子創薬に資するペプチド・核酸・糖鎖の合成技術2018

    • Author(s)
      千葉一裕
    • Total Pages
      218
    • Publisher
      シーエムシー出版
    • ISBN
      9784781313207
    • Related Report
      2017 Annual Research Report
  • [Book] Organic Electrochemistry, Fifth Edition2015

    • Author(s)
      Kazuhiro Chiba, Yohei Okada, Kevin Lam, William E. Geiger, Paola Ceroni, Alberto Cerdi, Margherita Venturi, Cyarille Costentin, Marc Robert, Jean-Michel Saveant and others
    • Total Pages
      1716
    • Publisher
      CRC Press
    • Related Report
      2015 Annual Research Report
  • [Book] 有機合成実験法ハンドブック第2版2015

    • Author(s)
      千葉一裕
    • Total Pages
      1202
    • Publisher
      丸善出版
    • Related Report
      2015 Annual Research Report
  • [Remarks] 東京農工大学生物有機化学研究室

    • URL

      http://web.tuat.ac.jp/~bio-org/

    • Related Report
      2017 Annual Research Report
  • [Remarks] 東京農工大学 生物有機化学研究室

    • URL

      http://web.tuat.ac.jp/~bio-org/

    • Related Report
      2015 Annual Research Report

URL: 

Published: 2015-04-16   Modified: 2019-03-29  

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