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Synthesis of 8-substituted purine chemical library and riboswitch-reengineering

Research Project

Project/Area Number 23241073
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical biology
Research InstitutionOsaka University

Principal Investigator

NAKATANI Kazuhiko  大阪大学, 産業科学研究所, 教授 (70237303)

Co-Investigator(Kenkyū-buntansha) TAKEI Fumie  大阪大学, 産業科学研究所, 助教 (30252711)
HAGIHARA Masaki  弘前大学, 理工学研究科, 准教授 (40403000)
Research Collaborator DOHNO Chikara  大阪大学, 産業科学研究所, 准教授 (60420395)
MURATA Asako  大阪大学, 産業科学研究所, 助教 (50557121)
FUKUZUMI Takeo  大阪大学, 産業科学研究所, 特任助教 (00592768)
AIKAWA Haruo  大阪大学, 産業科学研究所, 特任助教 (70547322)
Project Period (FY) 2011-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥49,270,000 (Direct Cost: ¥37,900,000、Indirect Cost: ¥11,370,000)
Fiscal Year 2013: ¥16,250,000 (Direct Cost: ¥12,500,000、Indirect Cost: ¥3,750,000)
Fiscal Year 2012: ¥15,730,000 (Direct Cost: ¥12,100,000、Indirect Cost: ¥3,630,000)
Fiscal Year 2011: ¥17,290,000 (Direct Cost: ¥13,300,000、Indirect Cost: ¥3,990,000)
Keywordssynthesis / 8-substituted purine / chemical library / riboswitch / reengineering / 8位置換プリン誘導体 / in vivo セレクション / リボスイッチ / doped library / 8位置換プリン化合物 / ライブラリー / 8位置換プリン / インビトロセレクション
Outline of Final Research Achievements

In the projet "Synthesis of 8-substituted purine chemical library and ribolswitch-reengineering", we have focused our attention on the synthesis of compound library of 8-substituted purim derivatives, and the application of compounds for the regulation of artificial riboswitches. The synthesis of 8-substituted purine derivatives were successfully done by a coupling of 8-bromo-adenine and 8-bromo-adenosine with the commercially available borate esters under Suzuki-Miyaura coupling conditions, providing us a chemical library of 8-substituted purines. With these compounds in hand, we looked for the RNA functioning as riboswiches by in vitro selection using doped library of adenine riboswitch. We have changed the selection conditions, the desired RNA functioning as riboswitch could not be selected. The lack of diversity of RNA sequence was one of reason for these results.

Report

(4 results)
  • 2014 Final Research Report ( PDF )
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • 2011 Annual Research Report
  • Research Products

    (50 results)

All 2015 2014 2013 2012 Other

All Journal Article (24 results) (of which Peer Reviewed: 23 results,  Open Access: 2 results,  Acknowledgement Compliant: 4 results) Presentation (26 results) (of which Invited: 9 results)

  • [Journal Article] 2-Aminophenanthroline dimer stabilized the C-C mismatched duplex DNA2015

    • Author(s)
      Li, J.; Matsumoto, J. Otabe, K.; Dohno, C.; Nakatani, K.
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 23 Issue: 4 Pages: 753-758

    • DOI

      10.1016/j.bmc.2014.12.062

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Detection of hepatitis C virus by single-step hairpin primer RT-PCR2014

    • Author(s)
      Takei, F.; Tani, H.; Matsuura Y.; Nakatani, K.
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 24 Pages: 394-396

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Formation of Ligand-Assisted Complex of Two RNA Hairpin Loops2014

    • Author(s)
      Changfeng Hong, Takahiro Otabe, Saki Matsumoto, Chikara Dohno, Asako Murata, Masaki Hagihara, Kazuhiko Nakatani
    • Journal Title

      Chem. Eur. J.

      Volume: 20 Issue: 18 Pages: 5244-5252

    • DOI

      10.1002/chem.201304683

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Modulation of binding properties of amphiphilic DNA containing multiple dodecyl phosphotriester linkages to lipid bilayer membrane2014

    • Author(s)
      Makishi, S.; Shibata, T.; Okazaki, M.; Dohno, C.; Nakatani, K.
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 24 Issue: 15 Pages: 3578-3581

    • DOI

      10.1016/j.bmcl.2014.05.042

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 8-substituted adenine and adenosine libraries and the binding to pre-miR-29a2014

    • Author(s)
      Fukuzumi, T.; Aikawa, H.; Harada, Y.; Sugai, A.; Murata, A.; Nakatani, K.
    • Journal Title

      Bull. Chem. Soc. Jpn.

      Volume: 87 Issue: 9 Pages: 1013-1015

    • DOI

      10.1246/bcsj.20140137

    • NAID

      130004687252

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Cytosine-bulge dependent fluorescence quenching for real-time hairpin primer PCR2014

    • Author(s)
      Takei, F.; Chen, X.; Yu, G.; Shibata, T.; Dohno, C.; Nakatani, K.
    • Journal Title

      Chem. Commun.

      Volume: 50 Issue: 96 Pages: 15195-15198

    • DOI

      10.1039/c4cc06780k

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Recognition of Chelerythrine to Human Telomeric DNA and RNA G-quadruplexes2014

    • Author(s)
      Bai, L.-P.; Hagihara, M.; Nakatani, K.; Jiang, Z.-H.
    • Journal Title

      Sci. Rep.

      Volume: 4 Issue: 1 Pages: 6767-6767

    • DOI

      10.1038/srep06767

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Selective recognition of G-G mismatch using the double functional probe with electrochemical active ferrocenyl2013

    • Author(s)
      He, H.; Xia, J.; Chang, G.; Peng, X.; Lou, Z.; Nakatani, K.; Zhou, X.; Wang, S.
    • Journal Title

      Biosensors and Bioelectronics

      Volume: 42 Pages: 36-40

    • DOI

      10.1016/j.bios.2012.10.042

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Novel DANP-Coupled Hairpin RT-PCR for Rapid Detection of Chikungunya Virus.2013

    • Author(s)
      Chen, H.; Takei, F.; Koay, E. S.-C.; Nakatani, K.; Chu, J. J. H.
    • Journal Title

      J. Mol. Diagn.

      Volume: 15 Issue: 2 Pages: 227-233

    • DOI

      10.1016/j.jmoldx.2012.10.004

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Ligand-induced electron spin-assembly on a DNA tile2013

    • Author(s)
      H. Atsumi, S. Nakazawa, C. Dohno, K. Sato, T. Takui, K. Nakatani
    • Journal Title

      Chemical Communications

      Volume: 49 Issue: 57 Pages: 6370-6372

    • DOI

      10.1039/c3cc41801d

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ligand-inducible formation of RNA pseudoknot2013

    • Author(s)
      Matsumoto, S., Hong, C; Otabe, T.; Murata, A.; Nakatani, K.
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 23 Issue: 12 Pages: 3539-3541

    • DOI

      10.1016/j.bmcl.2013.04.037

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] G-quadruplex formation of entirely hydrophobic DNA in organic solvents2013

    • Author(s)
      Shibata, T.; Dohno, C.; Nakatani, K.
    • Journal Title

      Chem. Commun.

      Volume: 49 Issue: 48 Pages: 5501-5503

    • DOI

      10.1039/c3cc42221f

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A synthetic riboswitch that operates using a rationally designed ligand-RNA pair2013

    • Author(s)
      Dohno, C.; Kohyama, I.; Kimura, M.; Hagihara, M.; Nakatani, K.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 52 Issue: 38 Pages: 9976-9979

    • DOI

      10.1002/anie.201303370

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Fluorescent indicator displacement assay of ligands targeting 10 microRNA precursors2013

    • Author(s)
      Murata, A.; Harada, Y.; Fukuzumi, T.; Nakatani, K.
    • Journal Title

      Bioorg. Med. Chem.

      Volume: 21 Issue: 22 Pages: 7101-7106

    • DOI

      10.1016/j.bmc.2013.09.007

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Facile electrochemical biosensor based on a new bifunctional probe for label-free detection of CGG trinucleotide repeat2013

    • Author(s)
      He, H.; Xia, J. P.; Peng, X. Q.; Chang, G.; Zhang, X. H.; Wang, Y. F.; Nakatani, K.; Lou, Z. W.; Wang, S. F.
    • Journal Title

      Biosensors and Bioelectronics

      Volume: 49 Pages: 282-289

    • DOI

      10.1016/j.bios.2013.05.022

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] High speed DNA denaturation using microheating devices2013

    • Author(s)
      Furuhashi, M.; Okamoto, Y.; Onoshima, D.; Ohshiro, T.; Ryuzaki, S.; Yokota, K.; Tsutsui, M.; Taniguchi, M.; Nakatani, K.; Baba, Y.; Kawai, T.
    • Journal Title

      Appl. Phys. Lett.

      Volume: 103 Pages: 023112-023112

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Triethynylmethane: A Molecular Unit Inducing Excimer-Like Emission in Aggregated States of Hydrocarbon Fluorophores2013

    • Author(s)
      Otabe, T.; Matsumoto, S.; Nakagawa, H.; Hong, C.; Dohno, C.; Nakatani, K.
    • Journal Title

      Tetrahedron. Lett.

      Volume: 54 Pages: 143-146

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Naphthyridine tetramer with a preorganized structure for 1:1 binding to a CGG/CGG sequence.2012

    • Author(s)
      Dohno, C.; Kohyama, I.; Hong, C.; Nakatani, K.
    • Journal Title

      Nucleic. Acids. Res.

      Volume: 40 Pages: 2771-2781

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Small Molecule Regulates Hairpin Structures in d(CGG) Trinucleotide Repeats2012

    • Author(s)
      Hagihara, M.; He, H.; Kimura, M.; Nakatani, K.
    • Journal Title

      Bioorg. Med. Chem. Lett.

      Volume: 22 Pages: 2000-2003

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Structure-activity studies on the fluorescent indicator in the displacement assay for the screening of small molecules binding to RNA2012

    • Author(s)
      Umemoto, S.; Im, S.; Zhang, J.; Hagihara, M.; Murata, A.; Harada, Y.; Fukuzumi, T.; Wazaki, T.; Sasaoka, S.; Nakatani, K.
    • Journal Title

      Chem. Eur. J.

      Volume: 18 Pages: 9999-10008

    • Related Report
      2012 Annual Research Report
  • [Journal Article] Takei, F.; Igarashi, M.; Oka, Y.; Koga, Y.; Nakatani, K2012

    • Author(s)
      Competitive allele-specific hairpin primer PCR for extremely high allele discrimination in typing of single nucleotide polymorphism
    • Journal Title

      ChemBioChem

      Volume: 13 Pages: 1409-1412

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Assembly of a small DNA rectangular parallelepiped block into higher order nanostructures2012

    • Author(s)
      Nakagawa, H.; Toda, M.; Atsumi, H.; Hagihara, M.; Hayashi-Nishino, M.; Dohno, C.; Nakatani, K.
    • Journal Title

      Chem. Lett.

      Volume: 41 Pages: 1550-1552

    • NAID

      10031126595

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Activation of prokaryotic translation by antisense oligonucleotides binding to coding region of mRNA2012

    • Author(s)
      Hayashi, G.; Hong, C.; Hagihara, M.; Nakatani, K.
    • Journal Title

      Biochem. Biophys. Res. Commun.

      Volume: 429 Pages: 105-110

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Small Molecule Regrulates Hairpin Structures in d(CGG) Trinucleotide Repeats2012

    • Author(s)
      K.Nakatani, M.Hagihara, H.He, M.Kimura
    • Journal Title

      Bioorg.Med.Chem.Lett.

      Volume: 22 Issue: 5 Pages: 2000-2003

    • DOI

      10.1016/j.bmcl.2012.01.030

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Presentation] Regulation of RNA Secondary Structure and Function2014

    • Author(s)
      Kazuhiko Nakatani
    • Organizer
      Imaging and Sensing Biomolecular Function and Assembly
    • Place of Presentation
      University of Bordeaux
    • Year and Date
      2014-03-14
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Small Organic Molecules Regulating RNA Structure and Function "2013

    • Author(s)
      Kazuhiko Nakatani
    • Organizer
      The 1st Osaka University - EPFL International Symposium
    • Place of Presentation
      銀杏会館、大阪大学
    • Year and Date
      2013-12-02 – 2013-12-04
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Toward Regulation of RNA Structure and Function by Small Molecules2013

    • Author(s)
      Kazuhiko Nakatani
    • Organizer
      A3RONA 2013 Kobe
    • Place of Presentation
      ポートピアホテル、神戸
    • Year and Date
      2013-08-30 – 2013-09-01
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Facile Detection of PCR Progress by Hairpin Primer PCR2013

    • Author(s)
      中谷和彦
    • Organizer
      東北大学電気通信研究所ー阪大産研 交流会
    • Place of Presentation
      蔵王、山形
    • Year and Date
      2013-07-31 – 2013-08-02
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Small Organic Molecules Regulating RNA Structure and Function2013

    • Author(s)
      Kazuhiko Nakatani
    • Organizer
      15th RNA meeting in Matsuyama
    • Place of Presentation
      松山
    • Year and Date
      2013-07-24 – 2013-07-26
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] ヘアピンプライマーPCR 法を使ったウイルス検出法の開発2013

    • Author(s)
      武井史恵、中谷和彦
    • Organizer
      日本ケミカルバイオロジー学会 第8回年会
    • Place of Presentation
      東京医科歯科大学
    • Year and Date
      2013-06-19 – 2013-06-21
    • Related Report
      2013 Annual Research Report
  • [Presentation] 小分子で誘起されたRNAシュードノット構造によるフレームシフト機構の制御2013

    • Author(s)
      松本咲、洪昌峰、村田亜沙子、中谷和彦
    • Organizer
      日本ケミカルバイオロジー学会 第8回年会
    • Place of Presentation
      東京医科歯科大学
    • Year and Date
      2013-06-19 – 2013-06-21
    • Related Report
      2013 Annual Research Report
  • [Presentation] HIV-1 mRNAの部分構造RREと低分子の相互作用解析2013

    • Author(s)
      津田哲哉・福澄岳雄・中谷和彦
    • Organizer
      日本ケミカルバイオロジー学会 第8回年会
    • Place of Presentation
      東京医科歯科大学
    • Year and Date
      2013-06-19 – 2013-06-21
    • Related Report
      2013 Annual Research Report
  • [Presentation] Targeting secondary structures of pre-miRNA by small molecules : Development of potential inhibitors of pre-miRNA processing2013

    • Author(s)
      Asako Murata, Ayako Sugai, Takeo Fukuzumi, Shiori Umemoto, Chikara Dohno, Kazuhiko Nakatani
    • Organizer
      RNA 2013, the 18th Annual Meeting of the RNA Society
    • Place of Presentation
      Congress Center Davos, Davos, Switzerland
    • Year and Date
      2013-06-11 – 2013-06-16
    • Related Report
      2013 Annual Research Report
  • [Presentation] Suppression of miR-29a maturation by ligand binding2013

    • Author(s)
      OTABE, Takahiro; MURATA, Asako; TAKEI, Fumie; NAKATANI, Kazuhiko
    • Organizer
      RNA 2013, the 18th Annual Meeting of the RNA Society
    • Place of Presentation
      Congress Center Davos, Davos, Switzerland
    • Year and Date
      2013-06-11 – 2013-06-16
    • Related Report
      2013 Annual Research Report
  • [Presentation] Translational regulation by ligand-inducible formation of RNA pseudoknot2013

    • Author(s)
      Saki Matsumoto, Changfeng Hong, Asako Murata, Kazuhiko Nakatani
    • Organizer
      RNA 2013, the 18th Annual Meeting of the RNA Society
    • Place of Presentation
      Congress Center Davos, Davos, Switzerland
    • Year and Date
      2013-06-11 – 2013-06-16
    • Related Report
      2013 Annual Research Report
  • [Presentation] Coumarin fluorochrome binds to Rev responsible element RNA with extremely large absorption shift2013

    • Author(s)
      Tetsuya Tsuda, Takeo Fukuzumi, Kazuhiko Nakatani
    • Organizer
      RNA 2013, the 18th Annual Meeting of the RNA Society
    • Place of Presentation
      Congress Center Davos, Davos, Switzerland
    • Year and Date
      2013-06-11 – 2013-06-16
    • Related Report
      2013 Annual Research Report
  • [Presentation] Small Organic Molecules regulating RNA Structure and Function2013

    • Author(s)
      K. Nakatani
    • Organizer
      International Symposium on Challenges in Chemical Biology (ISCCB2013)
    • Place of Presentation
      カルカッタ
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] A. Murata, Y. Harada, T. Fukuzumi, S. Umemoto, S. Im, M. Hagihara, K. Nakatani2012

    • Author(s)
      High-throughput Screening of Chemical Libraries for the Discovery of RNA-binding Compounds
    • Organizer
      RNA 2012, the 17th Annual Meeting of the RNA Society
    • Place of Presentation
      ミシガン大学 USA
    • Related Report
      2012 Annual Research Report
  • [Presentation] Synthesis of Small Molecule Library for pre-miRNA Secondary Structures2012

    • Author(s)
      T. Fukuzumi, A. Murata, Y. Harada, K. Nakatani
    • Organizer
      RNA 2012, the 17th Annual Meeting of the RNA Society
    • Place of Presentation
      ミシガン大学 USA
    • Related Report
      2012 Annual Research Report
  • [Presentation] Synthesis of Small Molecule Library for pre-miRNA Secondary Structures2012

    • Author(s)
      T. Fukuzumi, A. Murata, Y. Harada, K. Nakatani
    • Organizer
      IKCOC-12
    • Place of Presentation
      京都
    • Related Report
      2012 Annual Research Report
  • [Presentation] Coumarin derivatives as an indicator for interactions between RNA and small molecules2012

    • Author(s)
      T. Tsuda, T. Fukuzumi, K. Nakatani
    • Organizer
      The 7th Asia and Oceania Conference on Photochemistry 2012
    • Place of Presentation
      大阪
    • Related Report
      2012 Annual Research Report
  • [Presentation] High allelic discrimination in typing of single nucleotide polymorphisms using allele-specific hairpin primer PCR2012

    • Author(s)
      F. Takei, G. Yu, C. Dohno, K. Nakatani
    • Organizer
      ISNAC2012
    • Place of Presentation
      名古屋
    • Related Report
      2012 Annual Research Report
  • [Presentation] Synthesis and application of a new modified DNA having cytosine-bulge binding fluorescent molecule2012

    • Author(s)
      G. Yu, F. Takei, T. Shibata, C. Dohno, K. Nakatani
    • Organizer
      ISNAC2012
    • Place of Presentation
      名古屋
    • Related Report
      2012 Annual Research Report
  • [Presentation] Synthesis and evaluation of novel naphthyridine derivatives for binding to RNA bulge structure2012

    • Author(s)
      T. Otabe, G. Yu, F. Takei, K. Nakatani
    • Organizer
      ISNAC2012
    • Place of Presentation
      名古屋
    • Related Report
      2012 Annual Research Report
  • [Presentation] Translation regulation of gene expression by small molecule-induced pseudoknot formation2012

    • Author(s)
      S. Matsumoto, C. Hong, A. Murata, K. Nakatani
    • Organizer
      ISNAC2012
    • Place of Presentation
      名古屋
    • Related Report
      2012 Annual Research Report
  • [Presentation] Synthesis and evaluation of hydrophobic G-quadruplex2012

    • Author(s)
      T. Shibata, S. Makishi, C. Dohno, K. Nakatani
    • Organizer
      ISNAC2012
    • Place of Presentation
      名古屋
    • Related Report
      2012 Annual Research Report
  • [Presentation] Small Organic Molecules Regulating RNA Structure and Function2012

    • Author(s)
      K. Nakatani
    • Organizer
      The First International Symposium on Biofunctional Chemistry (ISBC2012)
    • Place of Presentation
      東京工業大学
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Formation of Ligand-Assisted Complex of Two RNA Hairpin Loops2012

    • Author(s)
      K. Nakatani
    • Organizer
      The 7th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-7)
    • Place of Presentation
      シンガポール
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Development of amphiphilic DNA for building of 2D nanostructure at hydrophobic-hydrophilic interface

    • Author(s)
      S. Makishi, T. Shibata, C. Dohno, K. Nakatani
    • Organizer
      The 5th edition of the Young Scientist Symposium by the European Institute of Chemistry and Biology (IECB)
    • Place of Presentation
      ボルドー大学、フランス
    • Related Report
      2012 Annual Research Report
  • [Presentation] Small Molecule Interaction to RNA

    • Author(s)
      K. Nakatani
    • Organizer
      A3RONA 2012 KOREA
    • Place of Presentation
      POSTEC, KOREA
    • Related Report
      2012 Annual Research Report
    • Invited

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

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