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Development of Non-Enzymatic Method to Translate D-Nucleic Acid to L-Nucleic Acid

Research Project

Project/Area Number 16K14028
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Bio-related chemistry
Research InstitutionHokkaido University

Principal Investigator

Taniguchi Tohru  北海道大学, 先端生命科学研究院, 助教 (00587123)

Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords鏡像体 / 核酸 / 構造解析 / キラリティー / らせん / 有機化学
Outline of Final Research Achievements

Aiming both at creation of mirror-image life and at development of nucleic acid drugs resistant to nucleases, this work studied toward creation of non-enzymatic reaction to translate D-nucleic acid to L-nucleic acid. During the synthesis of L-nucleotide monomers, we succeeded in developing an efficient glycosidation reaction to connect a sugar and a nucleobase. We also established a new method to elucidate the configuration and conformation of furanoside and nucleoside by using vibrational circular dichroism. L-Nucleotides obtained in this study were submitted to solid-state synthesis, which yielded several oligonucleotides containing L-nucleotides. Oligonucleotides containing L-methylcytidines showed high stability when forming a duplex with D-oligonucleotides.

Report

(3 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • Research Products

    (5 results)

All 2018 2017 2016

All Journal Article (2 results) (of which Peer Reviewed: 2 results,  Open Access: 1 results) Presentation (2 results) (of which Int'l Joint Research: 1 results,  Invited: 1 results) Book (1 results)

  • [Journal Article] Stereochemistry (and Conformation) of Nucleosides and Their Synthetic Precursors by Vibrational Circular Dichroism2018

    • Author(s)
      Tohru Taniguchi, Kie Nakano, Kenji Monde
    • Journal Title

      Current Protocols in Nucleic Acid Chemistry

      Volume: 72 Issue: 1

    • DOI

      10.1002/cpnc.50

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Analysis of Configuration and Conformation of Furanose Ring in Carbohydrate and Nucleoside by Vibrational Circular Dichroism2017

    • Author(s)
      Taniguchi, T., Nakano, K., Baba, R., Monde, K.
    • Journal Title

      Org. Lett.

      Volume: 19 Issue: 2 Pages: 404-407

    • DOI

      10.1021/acs.orglett.6b03626

    • Related Report
      2016 Research-status Report
    • Peer Reviewed
  • [Presentation] Determining Molecular Configuration and Conformation by Vibrational Circular Dichroism: from Small Molecules to Macromolecules2018

    • Author(s)
      谷口透
    • Organizer
      日本化学会第98回春季年会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Examination of the Effects of L-5-methylcytidine on the Structure and Stability of D-L Hybrid Double Helix2017

    • Author(s)
      Haruka Murabayashi, Tohru Taniguchi, Kenji Monde
    • Organizer
      第47回国際核酸化学シンポジウム
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Book] 化学(8月号)2016

    • Author(s)
      谷口透
    • Total Pages
      2
    • Publisher
      化学同人
    • Related Report
      2016 Research-status Report

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Published: 2016-04-21   Modified: 2019-03-29  

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