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Triazole-linked aminoacyl-tRNA to introduce variations of amino acids

Research Project

Project/Area Number 16K05836
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Bio-related chemistry
Research InstitutionThe University of Tokyo

Principal Investigator

Fujino Tomoko  東京大学, 物性研究所, 助教 (70463768)

Project Period (FY) 2016-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2018: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2017: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsトリアゾール / RNA / クリック化学 / mRNA / duplex / π積層 / 芳香族分子 / 二重鎖 / CuAAC / DNA / tRNA / 翻訳反応 / ヌクレオシド / アミノアシルtRNA / 非天然型アミノ酸 / ペプチド
Outline of Final Research Achievements

We developed a high-efficient synthesis method of triazole-linked nucleic acid using click chemistry for nucleic acid elongation reaction and realized its functional development in life science. In searching for a click-linking method between RNA and amino acid planned at the beginning, azidation to the DNA end and the click-linking method were developed. These methods enabled us to realize a convenient double-stranded DNA template preparation for next-generation DNA sequencers. In addition, we switched the research target from modified tRNA to more challenging modified mRNA without any examples. We realized modified mRNA with a non-phosphate-linked codon for the first time. We also clarified the effect of the triazole linkages in the double-strand formation of such modified RNA from the thermodynamic analysis.

Academic Significance and Societal Importance of the Research Achievements

非リン酸型核酸は高い化学的・熱力学的安定性に加え,多様な機能性が期待される次世代型バイオ材料であるが,その合成上の制約により機能展開に至った例はごく限られていた.本研究では,高効率なクリック化学に着目して,糖保存・非リン酸型RNAでの最長の例を実現し,その二重鎖形成における熱力学的特性を初めて明らかにした.さらにこうした非リン酸型の機能展開として,これまで例のない翻訳反応におけるmRNAとしての機能性評価や,次世代シークエンサーのための鋳型DNA調整法を実現した.本研究により,これまでほとんど明らかとなってきていない非リン酸型RNA・DNAの機能性開拓を達成した.

Report

(6 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (28 results)

All 2021 2020 2019 2017 2016 Other

All Journal Article (4 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 4 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (19 results) (of which Int'l Joint Research: 5 results,  Invited: 1 results) Remarks (4 results) Patent(Industrial Property Rights) (1 results) (of which Overseas: 1 results)

  • [Journal Article] The Simplest Model for Doped Poly(3,4‐ethylenedioxythiophene) (PEDOT): Single‐crystalline EDOT Dimer Radical Cation Salts2021

    • Author(s)
      Kameyama Ryohei、Fujino Tomoko、Dekura Shun、Kawamura Mitsuaki、Ozaki Taisuke、Mori Hatsumi
    • Journal Title

      Chemistry - A European Journal

      Volume: 27 Issue: 22 Pages: 6696-6700

    • DOI

      10.1002/chem.202005333

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Vapochromism induced by intermolecular electron transfer coupled with hydrogen-bond formation in zinc dithiolene complex2020

    • Author(s)
      Yokomori So、Dekura Shun、Fujino Tomoko、Kawamura Mitsuaki、Ozaki Taisuke、Mori Hatsumi
    • Journal Title

      Journal of Materials Chemistry C

      Volume: 8 Issue: 42 Pages: 14939-14947

    • DOI

      10.1039/d0tc04280c

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Duplex-forming oligonucleotide of triazole-linked RNA2019

    • Author(s)
      Fujino, T.; Suzuki, T.; Ooi, T.; Ikemoto, K; Isobe, H.
    • Journal Title

      Chem. Asian J.

      Volume: 14 Issue: 19 Pages: 3380-3385

    • DOI

      10.1002/asia.201901112

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Chimeric RNA oligonucleotides incorporating triazole-linked trinucleotides: Synthesis and function as mRNA in cell-free translation reactions2016

    • Author(s)
      Fujino, T.; Suzuki, T.; Okada, K.; Kogashi, K.; Yasumoto, K.; Sogawa, K.; Isobe, H. "
    • Journal Title

      J. Org. Chem.

      Volume: 81 Issue: 19 Pages: 8967-8976

    • DOI

      10.1021/acs.joc.6b01618

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] Charge Transfer Salts of Oligo(ethylenedichalcogenothiophene) (nEDXT: X = O, S) as Oligomer Models for Doped polyEDOT (PEDOT),2021

    • Author(s)
      T. Fujino, R. Kameyama, S. Dekura, K. Onozuka, K. Matsuo, H. Mori
    • Organizer
      The International Chemical Congress of Pacific Basin Societies (USA)
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Charge Transfer Complexes of Ethylenedichalcogenothiophene (EDCT:C = O, S) and TCNQ Analogs: Atom-substituted Effects2021

    • Author(s)
      藤野智子,亀山亮平, 小野塚洸太, 出倉駿, 森初果
    • Organizer
      日本化学会第101回春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Electron-transfer-induced Vapochromism Coupled with Hydrogen Bond in a Zinc Dithiolene Complex Crystal2021

    • Author(s)
      S. Yokomori, S. Dekura, T. Fujino, M, Kawamura, T. Ozaki, H. Mori
    • Organizer
      The International Chemical Congress of Pacific Basin Societies (USA)
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Electron-rich Nickel Dithiolene Complex: Synthesis and Field-effect Transistor Character2021

    • Author(s)
      伊藤雅聡, 藤野智子,Lei Zhang, 森初果
    • Organizer
      日本化学会第101回春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Synthesis of Novel Single-crystalline Ethylenedioxythiophene Oligomer Charge Transfer Salts and the Conjugation-length-elongation Effects on Their Physical Properties2021

    • Author(s)
      亀山亮平, 藤野智子,出倉駿, 河村光晶, 尾崎泰助, 森初果
    • Organizer
      日本化学会第101回春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 新規エチレンジオキシチオフェンオリゴマーおよびその電荷移動塩単結晶の合成ならびに共役長伸長効果2021

    • Author(s)
      亀山亮平,藤野智子,出倉駿,河村光晶,尾崎泰助,森初果
    • Organizer
      日本物理学会第76回秋季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Triazole-linked DNA and RNA: From Chiral Monomers to Oligomers and Duplexes2020

    • Author(s)
      T. Fujino, H. Isobe,
    • Organizer
      ISQBS, The 5th International Symposium of Quantum Beam Science -Chirality in Material Science: Current Status and Future Prospects-
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] The Simplified Model Systems for Doped PEDOT (poly(3,4-ethylenedioxythiophene)): Single-crystalline EDOT Oligomer Radical Cation Salts2020

    • Author(s)
      R. Kameyama, T. Fujino, S. Dekura, M. Kawamura, T. Ozaki, H. Mori
    • Organizer
      ISQBS, The 5th International Symposium of Quantum Beam Science -Chirality in Material Science: Current Status and Future Prospects-
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 導電性高分子PEDOT(poly(3,4-ethylenedioxythiophene))塩の単純化モデル:EDOT オリゴマー塩単結晶の合成と物性2020

    • Author(s)
      亀山亮平, 藤野智子,出倉駿, 河村光晶, 尾崎泰助, 森初果
    • Organizer
      分子科学オンライン討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Syntheses and Field-Effect Transistor Characteristics of Novel Nickel-Dithiolene Complexes with Methoxybenzene Moieties2019

    • Author(s)
      L. Zhang, S. Yokomori, D. Zhang, T. Fujino, S. Dekura, H. Mori
    • Organizer
      第13回分子科学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] Syntheses and Field-Effect Transistor Characteristics of Novel Nickel-Dithiolene Complexes with Methoxybenzene Moieties2019

    • Author(s)
      L. Zhang, T. Fujino, S. Yokomori, D. Zhang, S. Dekura, M. Lippmaa, H. Mori
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] Structures and Physical Properties of EDOT (3,4-Ehylenedioxythiophene) Dimer-based Molecular Crystals2019

    • Author(s)
      Ryohei Kameyama, Shun Dekura, Tomoko Fujino, Hatsumi Mori
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 新規Znジチオレン錯体結晶の構造とベイポクロミック特性2019

    • Author(s)
      横森創,出倉駿,藤野智子,尾崎泰助,森初果
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] 新規チオフェン系オリゴマーの合成およびその電荷移動錯体の伝導度測定2019

    • Author(s)
      亀山亮平,出倉駿,藤野智子,森初果
    • Organizer
      第13回分子科学討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] トリアゾール連結部を含むオリゴリボヌクレオチド類縁体:多重鎖形成とその熱力学的解析2019

    • Author(s)
      鈴木建,藤野智子,大井つぐみ,磯部寛之
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] ''Chimeric RNA oligonucleotides: Synthesis and function as mRNA in cell-free translation reactions''2017

    • Author(s)
      T, Fujino, T. Suzuki, K. Okada, K. Kogashi, K. Yasumoto, K. Sogawa, H. Isobe
    • Organizer
      The 44th International Symposium on Nucleic Acids Chemistry & The 1st Annual Meeting of Japan Society of Nucleic Acids Chemistry
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] Implementation of Non-natural, Triazole Linkers in mRNA Template for Translation Reactions2016

    • Author(s)
      鈴木建, 藤野智子, 岡田滉大, 古樫加奈子, 安元研一, 十川和博, 磯部寛之
    • Organizer
      平成28年度化学系学協会東北大会
    • Place of Presentation
      いわき明星大学(福島県・いわき市)
    • Year and Date
      2016-09-10
    • Related Report
      2016 Research-status Report
  • [Presentation] DNAチップの開発に向けた電気化学クリック反応による表面修飾2016

    • Author(s)
      坂本ちか,阿部博弥,伊野浩介,藤野智子,磯部寛之,珠玖仁,末永智一
    • Organizer
      化学とマイクロ・ナノシステム学会第34回研究会
    • Place of Presentation
      幕張メッセ国際会議場(千葉県・幕張市)
    • Year and Date
      2016-09-06
    • Related Report
      2016 Research-status Report
  • [Presentation] 電気化学クリック反応を利用した電極修飾2016

    • Author(s)
      坂本ちか,阿部博弥,伊野浩介,藤野智子,磯部寛之,珠玖仁,末永智一
    • Organizer
      平成28年度東日本分析化学若手交流会
    • Place of Presentation
      日本大学軽井沢研修所(長野県・軽井沢市)
    • Year and Date
      2016-07-01
    • Related Report
      2016 Research-status Report
  • [Remarks] 東京大学 物性研究所 凝縮系物性研究部門 森研究室

    • URL

      https://hmori.issp.u-tokyo.ac.jp/index.html

    • Related Report
      2020 Annual Research Report
  • [Remarks] 物性研究所・森研究室HP

    • URL

      https://hmori.issp.u-tokyo.ac.jp/index.html

    • Related Report
      2019 Research-status Report
  • [Remarks] 東京大学 理学系研究科 化学専攻 物理有機化学研究室

    • URL

      http://www.chem.s.u-tokyo.ac.jp/users/physorg/Main/Top.html

    • Related Report
      2017 Research-status Report
  • [Remarks] 物理有機化学研究室

    • URL

      http://www.chem.s.u-tokyo.ac.jp/users/physorg/Main/Top.html

    • Related Report
      2016 Research-status Report
  • [Patent(Industrial Property Rights)] 導電性オリゴマー、導電性組成物、導電助剤、前記導電性組成物を用いて形成された、コンデンサ用電極、透明電極、電池用電極、又はキャパシタ用電極2020

    • Inventor(s)
      [1]清野美勝,中村浩昭,森初果,藤野智子,出倉駿,亀山亮平
    • Industrial Property Rights Holder
      [1]清野美勝,中村浩昭,森初果,藤野智子,出倉駿,亀山亮平
    • Industrial Property Rights Type
      特許
    • Filing Date
      2020
    • Related Report
      2020 Annual Research Report
    • Overseas

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Published: 2016-04-21   Modified: 2022-01-27  

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