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Synthesis of Self-Replicating Peptide Ribonucleic Acid (PRNA) System withClick Chemistry

Research Project

Project/Area Number 23655096
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Polymer chemistry
Research InstitutionTohoku University

Principal Investigator

WADA Takehiko  東北大学, 多元物質科学研究所, 教授 (20220957)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2011: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords自己複製 / 自己増殖 / クリック反応 / 人工核酸 / 人工PCR / 分子認識 / ナノバイオ / ケミカルバイオロジー / クリックケミストリー
Research Abstract

We have recently proposed a new category of nucleic acid model, peptide ribonucleic acids (PRNAs), which possess isopoly-L-glutamine as a backbone structure in place of the conventional negatively charged phosphate-sugar backbone and 5'-amino-5'-deoxyribonucleosides tethered to the backbone through an amide linkage as the recognition site. We have also demonstrated that the base orientation of PRNA can be readily altered from anti to syn by adding borax as an external factor. In this study to give the self-replicative and self-duplication function to PRNA, the chemical modification of the PRNA forapplying “Click Reaction"have been discussed. The amino acid derivative containing ethynyl group atside chain was introduced into the oligo PRNA backbone. Then the ethynyl moiety was reacted with5'-azido-5'-deoxyribonucleoside derivative with “Click Reaction" to give a new type of PRNA.

Report

(3 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Research-status Report
  • Research Products

    (43 results)

All 2013 2012 2011 Other

All Journal Article (16 results) (of which Peer Reviewed: 16 results) Presentation (20 results) (of which Invited: 3 results) Book (6 results) Remarks (1 results)

  • [Journal Article] Remarkable Enhancement of Sensitivity with the Second Generation of Elliptically Polarization-detected Circular Dichroism Spectroscopy2013

    • Author(s)
      Murakami, M.; Araki, Y.; Sakamoto, S.; Hamada, Y.; Wada, T.
    • Journal Title

      Chem. Lett

      Volume: 42 Issue: 3 Pages: 261-262

    • DOI

      10.1246/cl.2013.261

    • NAID

      10031155773

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Double Helices of a Pyridine-Appended Zinc Chlorophyll Derivative2013

    • Author(s)
      Y. Shinozaki, G. Richards, K. Ogawa, A. Yamano, K. Ohara, K. Yamaguchi, S. Kawano, K. Tanaka, Y. Araki, T. Wada, and J. Otsuki
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 135 Issue: 14 Pages: 5262-5265

    • DOI

      10.1021/ja400493e

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Entrainer Effects on Enantiodifferentiating Photocyclization of 5-Hydroxy-1,1-diphenylpentene in Near- and Supercritical Carbon Dioxide2012

    • Author(s)
      Y. Nishiyama, T. Wada, K. Kakiuchi, Y. Inoue
    • Journal Title

      Journal of Organic Chemistry

      Volume: 77 Issue: 13 Pages: 5681-5686

    • DOI

      10.1021/jo300816w

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Microenvironmental Control of Enantiodifferentiating Photocyclization of 5-Hydroxy-1,1-diphenylpentene through Selective Solvation2012

    • Author(s)
      Y. Nishiyama, T. Wada, K. Kakiuchi, Y. Inoue
    • Journal Title

      Chirality

      Volume: 24 Issue: 5 Pages: 400-405

    • DOI

      10.1002/chir.22004

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Application of Photoactive Yellow Protein as a Photoresponsive Module for Controlling Hemolytic Activity of Staphylococcal α-Hemolysin2012

    • Author(s)
      M. Ui, et al.
    • Journal Title

      Chemical Communications

      Volume: 48 Issue: 39 Pages: 4737-4739

    • DOI

      10.1039/c2cc18118e

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Curing Depth of Light-activated Nanofiller containing Resin Composites2012

    • Author(s)
      Kanehira, M.; Araki, Y.; J Finger, W.; Wada, T.; Andreas, A. ; Komatsu, M.
    • Journal Title

      World Journal of Dentistry

      Volume: 3 Pages: 119-125

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Design of a dual-color detection system for caspase activities using a combination of split-fluorescent proteins and split-intein2012

    • Author(s)
      Sakamoto, Seiji; Terauchi, Mika; Taki, Shusaku; Kim, Tanner Ian; Araki, Yasuyuki; *Wada, Takehiko
    • Journal Title

      Peptide Sci

      Volume: 48 Pages: 325-326

    • NAID

      10030204493

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] New paradigm of biomolecular soft-interfaces as chiral reaction fields for supramolecular asymmetric photochirogenesis2012

    • Author(s)
      Wada, Takehiko
    • Journal Title

      Hyomen Kagaku

      Volume: 33 Pages: 27-33

    • NAID

      10030442978

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Planar-to-Planar Chirality Transfer in the Excited State. Enantiodifferentiating Photoisomerization of Cyclooctenes Sensitized by Planar-Chiral Paracyclophane2011

    • Author(s)
      R.Maeda, T.Wada, T.Mori, S.Kono, N.Kanomata, Y.Inoue
    • Journal Title

      Journal of the American Chemical Society

      Volume: 133 Issue: 27 Pages: 10379-10381

    • DOI

      10.1021/ja203781f

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Roles of Entropy in Supramolecular Photochirogenesis : Enantiodifferentiating Photoisomerization of Cyclooctenes in Chiral Sensitizer-Immobilized MCM-41 Cavities2011

    • Author(s)
      R.Maeda, T.Wada, A.Kusaka, T.Mori, M.Iwamoto, Y.Inoue
    • Journal Title

      Photochemical and Photobiological Sciences

      Volume: 10 Issue: 9 Pages: 1390-1392

    • DOI

      10.1039/c1pp05087g

    • Related Report
      2012 Final Research Report 2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Supramolecular Asymmetric Photochirogenesis with Biopolymers as a Chiral Confined Reaction Media2011

    • Author(s)
      Wada, Takehiko
    • Journal Title

      Polym.

      Volume: 60 Pages: 757-761

    • NAID

      10029658353

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Supramolecular Asymmetric Photochirogenesis with Biopolymers as a Chiral Confined Reaction Media2011

    • Author(s)
      Wada, Takehiko; Sakamoto, Seiji; Murakami, Makoto; Araki, Yasuyuki; Inoue, Yoshihisa.
    • Journal Title

      J. Photopoly. Sci. Tech.

      Volume: 24 Pages: 595-596

    • NAID

      10029658353

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of artificial nucleic acid and non-natural protein for active control of cellular function2011

    • Author(s)
      Wada, Takehiko; Araki, Yasuyuki; Sakamoto, Seiji
    • Journal Title

      Materials Integration

      Volume: 24 Pages: 10-16

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis, and application of artificial nucleic acids as a novel tool for chemical biology2011

    • Author(s)
      Wada, Takehiko
    • Journal Title

      Frontier of Chem.

      Volume: 22 Pages: 135-144

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] External Stimulation Responsive Artificial Nucleic Acids2011

    • Author(s)
      Wada, Takehiko
    • Journal Title

      Rev. CSJ. Curr. Rev.

      Volume: 6 Pages: 71-77

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Supramolecular Asymmetric Photochirogenesis with Biopolymers as a Chiral Reaction Field2011

    • Author(s)
      Wada, Takehiko
    • Journal Title

      J. Surf. Sci. Soc. Jap.

      Volume: 33 Pages: 27-33

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] 酵素やタンパク質表面を活用した化学反応制御法-環境調和型化学反応の実現を目指して2012

    • Author(s)
      和田健彦
    • Organizer
      ソフトインターフェースの分子科学「新技術発表会」
    • Place of Presentation
      東京大学山上会館,日本
    • Year and Date
      2012-11-09
    • Related Report
      2012 Final Research Report
  • [Presentation] 生体高分子の機能材料への展開と動的機能制御‐核酸とタンパク質の特性活用を目指して‐2012

    • Author(s)
      和田健彦
    • Organizer
      量子化学研究協会研究所公開講座
    • Place of Presentation
      京都大学桂キャンパス
    • Year and Date
      2012-04-18
    • Related Report
      2012 Final Research Report
  • [Presentation] Time-Resolved CD Apparatus with Ellipticity-Change-Detection System Toward the Application to High Sensitive Detection for the DNA/RNA Structural and Conformational Change2012

    • Author(s)
      Wada, T.
    • Organizer
      Special Lecture in IECB Univ. of Bordeaux at the IECB
    • Place of Presentation
      Bordeaux, France
    • Year and Date
      2012-03-06
    • Related Report
      2012 Final Research Report
  • [Presentation] Novel Strategy for Cancer Cell Specific Oligonucleotide Therapeutics with Intracellular Environmental Condition Responsible Artificial Nucleic Acid: Peptide Ribonucleic Acids (PRNA)2012

    • Author(s)
      Wada, T.
    • Organizer
      3rd Campus Asia Symposium
    • Place of Presentation
      Sendai, Japan
    • Related Report
      2012 Annual Research Report 2012 Final Research Report
  • [Presentation] Novel Strategy for Cancer Cell Specific Oligonucleotide Therapeutics with Intracellular Environmental Condition Responsible Artificial Nucleic Acid: PeptideRibonucleic Acids (PRNA)2012

    • Author(s)
      Wada, T.
    • Organizer
      5th Szeged International Workshop on Advances in Nanoscience (SIWAN)
    • Place of Presentation
      Szeged, Hungary
    • Related Report
      2012 Final Research Report
  • [Presentation] Novel Strategy for Cancer Cell Specific Oligonucleotide Therapeutics with Intracellular Environmental Condition Responsible Artificial Nucleic Acid: Peptide Ribonucleic Acids (PRNA)2012

    • Author(s)
      Wada, T.
    • Organizer
      International Conference on Emerging Advanced Nanomaterials2012 (ICEAN2012)
    • Place of Presentation
      Brisbane, Australia
    • Related Report
      2012 Annual Research Report 2012 Final Research Report
  • [Presentation] 生体高分子の機能材料への展開と動的機能制御2012

    • Author(s)
      和田健彦
    • Organizer
      第61回高分子討論会
    • Place of Presentation
      名古屋大学,日本
    • Related Report
      2012 Final Research Report
  • [Presentation] 刺激応答性人工核酸系を活用した新規がん細胞特異的遺伝子治療薬の構築2012

    • Author(s)
      和田健彦
    • Organizer
      平成24年度化学系学協会東北大会
    • Place of Presentation
      秋田大学,日本
    • Related Report
      2012 Final Research Report
  • [Presentation] Novel Strategy of Supramolecular Asymmetric Photochirogenesis with Tailor-made Biopolymers as Chiral Reaction Media2012

    • Author(s)
      Wada, T.
    • Organizer
      IUPAC Photochemistry, Coimbra
    • Place of Presentation
      Portugal
    • Related Report
      2012 Final Research Report
  • [Presentation] 生体高分子をキラルナノリアクターとして活用する超分子不斉光反応系の創製‐環境調和型不斉光化学反応系構築を目指して‐2012

    • Author(s)
      和田健彦
    • Organizer
      「ナノ構造・物性」第4回研究会
    • Place of Presentation
      神戸大
    • Related Report
      2012 Final Research Report
  • [Presentation] Novel Strategy for Cancer Cell Specific Oligonucleotide Therapeutics with Intracellular Environmental Condition Responsible Artificial Nucleic Acid: Peptide Ribonucleic Acids (PRNA)2012

    • Author(s)
      Takehiko WADA
    • Organizer
      Szeged International Workshop on Advances in Nanoscience (SIWAN)
    • Place of Presentation
      Szeged, Hungary
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] 生体高分子の機能材料への展開と動的機能制御2012

    • Author(s)
      和田健彦
    • Organizer
      第61回高分子討論会
    • Place of Presentation
      名古屋, 日本
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] 刺激応答性人工核酸系を活用した新規がん細胞特異的遺伝子治療薬の構築2012

    • Author(s)
      和田健彦
    • Organizer
      平成24年度化学系学協会東北大会
    • Place of Presentation
      秋田, 日本
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] 新規高感度・高時間分解能円二色性(CD)検出システムの開発‐機能性生体分子構造変化の動的挙動解明を目指して‐2011

    • Author(s)
      和田健彦
    • Organizer
      第13回歯工学連携講演会
    • Place of Presentation
      北九州
    • Year and Date
      2011-11-29
    • Related Report
      2012 Final Research Report
  • [Presentation] 細胞内環境応答型人工核酸の創製-がん細胞特異的がん治療薬の構築を目指して‐2011

    • Author(s)
      和田健彦
    • Organizer
      第5回バイオ関連シンポ
    • Place of Presentation
      つくば
    • Year and Date
      2011-09-13
    • Related Report
      2012 Final Research Report
  • [Presentation] Novel Strategy for Cancer Cell Specific Oligonucleotide Therapeutics with Intracellular Environmental Condition Responsible Peptide Ribonucleic Acids (PRNA)2011

    • Author(s)
      Wada, T
    • Organizer
      The 4th G-COE symposium, August18
    • Place of Presentation
      Sendai, Japan
    • Year and Date
      2011-08-18
    • Related Report
      2012 Final Research Report
  • [Presentation] ファージディスプレイ法を活用した新規超分子不斉光反応系の構築2011

    • Author(s)
      和田健彦・菅原唯・宮地亜有実・湊咲絵・坂本清志・木戸誠・宇井美穂子・荒木保幸・西嶋政樹・金原数・井上佳久
    • Organizer
      第60回高分子討論会
    • Place of Presentation
      岡山
    • Related Report
      2012 Final Research Report
  • [Presentation] ペプチドリボ核酸-DNAキメラ人工核酸の合成と核酸認識および遺伝情報発現制御への展開-32011

    • Author(s)
      和田健彦・水谷達哉・上松亮平・坂本清志・荒木保幸・山吉麻子・村上章
    • Organizer
      第60回高分子討論会
    • Place of Presentation
      岡山
    • Related Report
      2012 Final Research Report
  • [Presentation] Novel strategy for cancer cell specific oligonucleotide therapeutics with intracellular environmental condition responsible Peptide Ribonucleic Acids2011

    • Author(s)
      Wada, T., Tatsuya Mizutani, Akira Nagami, Seiji Sakamoto, Yasuyuki Araki, Shiroh Futaki, Yoshihisa Inoue
    • Organizer
      Controlled Release Society (CRS) Annual Meeting, 1st August
    • Place of Presentation
      Washington DC, USA
    • Related Report
      2012 Final Research Report
  • [Presentation] Nobel Strategy for External Stimulus Responsible Artificial Nucleic Acids - Toward the Creation of Cancer Cell Specific Gene Therapeutic Oligonucleotides2011

    • Author(s)
      Wada, Takehiko
    • Organizer
      1st France-Japan Work shop on Bio-Inspired Approaches,(招待講演)
    • Place of Presentation
      Bordeaux, France
    • Related Report
      2011 Research-status Report
  • [Book] 生体高分子をキラル反応場として活用した超分子不斉光化学系の創製‐環境調和型不斉合成法の開発を目指して‐2011

    • Author(s)
      和田健彦
    • Publisher
      高分子(高分子学会出版)
    • Related Report
      2012 Final Research Report
  • [Book] 刺激応答性人工核酸,核酸化学のニュートレンド‐DNA・RNAの新たな可能性を拓く‐2011

    • Author(s)
      和田健彦
    • Publisher
      化学同人(株)
    • Related Report
      2012 Final Research Report
  • [Book] 4.生物に学ぶ機能制御法‐細胞内環境応答性人工核酸の創製-,次世代バイオミメティックス研究の最前線2011

    • Author(s)
      和田健彦
    • Publisher
      CMC出版
    • Related Report
      2012 Final Research Report
  • [Book] フロンティア生命化学研究会にとっての世界化学年…2011

    • Author(s)
      和田健彦
    • Publisher
      生命化学研究会レター(日本化学会出版)
    • Related Report
      2012 Final Research Report
  • [Book] 耐震補強工事の思わぬ「弱点」‐東北大学多元研の例から‐2011

    • Author(s)
      和田健彦
    • Publisher
      化学(化学同人(株))
    • Related Report
      2012 Final Research Report
  • [Book] 阪神淡路大震災、そして東北地区太平洋沿岸地震(東日本大震災)を経験して…2011

    • Author(s)
      和田健彦
    • Publisher
      生命化学研究会レター(日本化学会出版)
    • Related Report
      2012 Final Research Report
  • [Remarks]

    • URL

      http://www.tagen.tohoku.ac.jp/labo/wada/index-j.html

    • Related Report
      2012 Final Research Report

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Published: 2011-08-05   Modified: 2019-07-29  

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