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Practical synthesis of oligonucleotides containing epigenetic cytosines

Research Project

Project/Area Number 17K15431
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionTokushima Bunri University

Principal Investigator

Ito Yuta  徳島文理大学, 薬学部, 助教 (90783225)

Project Period (FY) 2017-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2018: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2017: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsエピジェネティック修飾シトシン / オリゴ核酸 / 5-トリフルオロメチルシトシン / 5-カルボキシシトシン / オリゴ核酸合成後修飾 / エピジェネティック修飾 / 有機化学 / 核酸化学
Outline of Final Research Achievements

A concise and practical synthesis of oligonucleotides containing 5-carboxycytosine, which is one of the epigenetic cytosine nucleosides and thought to be involved in regulating gene expression, was developed. The trifluoromethyl group was successfully converted into carboxylic acid by treatment of oligonucleotides containing 5-trifluoromethylcytosine with alkaline solution. Furthermore, this method can be applied to post-synthetic modification of oligonucleotides containing 5-trifluoromethylpyrimidine bases for the preparation of a variety of modified oligonucleotides.

Academic Significance and Societal Importance of the Research Achievements

エピジェネティック修飾シトシンをオリゴ核酸へと導入するために必要なアミダイト体(原料)は非常に高価(5-カルボキシシトシンホスホロアミダイト: 約13万円/250mg)であるため、これら原料を安価に供給する手法の開発が必要不可欠である。したがって、本手法は5-カルボキシシトシン導入オリゴ核酸を簡便かつ安価に合成する手法としてエピジェネティクス研究の発展に資するツールになると期待される。また、トリフルオロメチル基を様々な置換基へと変換できることから、オリゴ核酸合成後修飾法として機能性オリゴ核酸創出への展開も期待される。

Report

(3 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • Research Products

    (8 results)

All 2019 2018 2017 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results,  Open Access: 1 results) Presentation (5 results) (of which Int'l Joint Research: 1 results) Remarks (1 results)

  • [Journal Article] Post-synthetic modification of oligonucleotides containing 5-trifluoromethylpyrimidine bases2018

    • Author(s)
      Yuta Ito, Misaki Matsuo, Kazuki Yamamoto, Wakana Yamashita, Takashi Osawa, Yoshiyuki Hari
    • Journal Title

      Tetrahedron

      Volume: 74 Issue: 47 Pages: 6854-6860

    • DOI

      10.1016/j.tet.2018.10.006

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Triplex- and Duplex-Forming Abilities of Oligonucleotides Containing 2′-Deoxy-5-trifluoromethyluridine and 2′-Deoxy-5-trifluoromethylcytidine2017

    • Author(s)
      Y. Ito, M. Matsuo, T. Osawa, Y. Hari
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 65 Issue: 10 Pages: 982-988

    • DOI

      10.1248/cpb.c17-00530

    • NAID

      130006109934

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] オリゴ核酸合成後修飾を利用したピリミジン塩基5位へのカルボン酸等価体導入法2019

    • Author(s)
      伊藤勇太,松尾美咲,山本一輝,山下若菜,大澤昂志,張 功幸
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] Post-synthetic conversion of 5-trifluoromethylpyrimidine bases within oligonucleotides2018

    • Author(s)
      Yuta Ito, Misaki Matsuo, Kazuki Yamamoto, Wakana Yamashita, Takashi Osawa, Yoshiyuki Hari
    • Organizer
      The 45th International Symposium on Nucleic Acids Chemistry
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 5-トリフルオロメチルピリミジン塩基を含むオリゴ核酸の直接的化学変換法2018

    • Author(s)
      松尾美咲,伊藤勇太,大澤昂志,張 功幸
    • Organizer
      第1回 日本核酸化学会 中四国地区セミナー
    • Related Report
      2018 Annual Research Report
  • [Presentation] α,α,α-トリフルオロチミジン含有オリゴ核酸の直接的化学変換法2018

    • Author(s)
      松尾美咲,伊藤勇太,大澤昂志,張 功幸
    • Organizer
      日本薬学会第138年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] α,α,α-トリフルオロチミジン含有オリゴ核酸の直接的化学変換法2018

    • Author(s)
      松尾美咲、伊藤勇太、大澤昂志、張 功幸
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Research-status Report
  • [Remarks] 徳島文理大学薬学部 放射薬品学教室

    • URL

      http://p.bunri-u.ac.jp/lab06

    • Related Report
      2018 Annual Research Report

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Published: 2017-04-28   Modified: 2020-03-30  

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