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Development of Novel Spin-labeled Nucleosides which detect base-pairing

Research Project

Project/Area Number 15590012
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionKYUSHU UNIVERSITY

Principal Investigator

ASO Mariko  Kyushu University, Graduate School of Pharmaceutica ISciences, Research Associate, 大学院・薬学研究院, 助手 (30201891)

Co-Investigator(Kenkyū-buntansha) SUEMUNE Hiroshi  Kyushu University, Graduate School of Pharmaceutica ISciences, Professor, 大学院・薬学研究院, 教授 (20095897)
Project Period (FY) 2003 – 2004
Project Status Completed (Fiscal Year 2004)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2004: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 2003: ¥2,200,000 (Direct Cost: ¥2,200,000)
Keywordsspin-labeled nucleoside / N-tert-butylaminoxyl / EPR / base pairing / hydrogen bonding / ESRスペクトル / pH依存症 / N-tert-アミノキシルラジカル / イノシン / アデノシン / シチジン / グアノシン
Research Abstract

We designed novel spin-labeled nucleosides, in which a spin source, an N-tert-butylaminoxyl radical, was directly attached to nucleobase. 2-N-tert-Butylaminoxyladenosine, 2-N-tert-butylaminoxylinosine, and 8-N-tert-butylaminoxylinosine, and 5-N-tert-butylaminoxylcytidine derivative were synthesized and thier stabilities and properties were studied by using electron peramagnetic resonance(EPR). It was of interest to investigate if EPR spectra of N-tert-butylaminoxylnucleosides changed upon formation of hydrogen bonding with complementary base. EPR spectra of O-silylated-5-N-tert-butylaminoxylcytidine in CH_2Cl_2 changed upon addition of O-silylated guanosine, which might form hydrogen bonds with the aminoxyl cytidine. 2-N-tert-Butylaminoxyladenosine was introduced into oligoncleotide and its EPR spectra were measured. The EPR spectrum of the obtained oligonucleotide showed three lines in phosphate buffer. The high line disappeared upon duplex formation with the complementary strand to show that the EPR spectra might give useful information on the structure of oligonucleotide. EPR spectra of 2-N-tert-butylaminoxylinosine showed pH dependency due to structural change of purine moiety

Report

(3 results)
  • 2004 Annual Research Report   Final Research Report Summary
  • 2003 Annual Research Report
  • Research Products

    (9 results)

All 2005 2004 2003 Other

All Journal Article (7 results) Publications (2 results)

  • [Journal Article] Synthesis and EPR studies of 2-N-tert-butylaminoxylpurine Derivatives2005

    • Author(s)
      T.Kaneko, M.Aso, N.Koga, H.Suemune
    • Journal Title

      Org.Lett 2

      Pages: 303-306

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthesis and EPR studies of 2-N-tert-butylaminoxylpurine Derivatives2005

    • Author(s)
      T.Kaneko, M.Aso, N.Koga, H.Suemune
    • Journal Title

      Org.Lett. 2

      Pages: 303-306

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Annual Research Report 2004 Final Research Report Summary
  • [Journal Article] Molecular design of novel spin-labeled nucleoside directly attached base moiety2004

    • Author(s)
      T.Kaneko, T.Katsurabara, Y.Matsui, M.Aso, N.Koga, H.Suemune
    • Journal Title

      Nucleic Acids Simposium Series 48

      Pages: 5-6

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Molecular design of novel spin-labeled nucleoside directly attached base moiety2004

    • Author(s)
      T.Kaneko, T.Katsurabara, Y.Matsui, M.Aso, N.Koga, H.Suemune
    • Journal Title

      Nucleic Acid Simposium Series 48

      Pages: 5-6

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Molecular design of novel spin-labeled nucleoside directly attached hase moiety2004

    • Author(s)
      Kaneko, T.Katsurabara, Y.Matsui, M.Aso, N.Koga, H.Suemune
    • Journal Title

      Nucleic Acids Simposium Series 48

      Pages: 5-6

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Synthetic studies and properties of N-tert-butylaminoxyl nucleosides2003

    • Author(s)
      M.Aso, T.Kaneko, M.Nakamura, Y.Matsui, N.Koga, H.Suemune
    • Journal Title

      Nucleic Acids Research Supplement 3

      Pages: 9-10

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Synthetic studies and properties of N-tert-butylaminoxylnucleosides2003

    • Author(s)
      M.Aso, T.Kaneko, M.Nakamura, Y.Matsui, N.Koga, H.Suemune
    • Journal Title

      Nucleic Acids Research 3(Supplement)

      Pages: 9-10

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Publications] M.Aso et al.: "A simple and efficient method for synthesis of 5-substituted 2'-deoxyuridine nucleosides using metal-halogen exchange reaction of 5-iodo-2'-deoxyuridine sodium salt"Chemical Communications. 2. 1094-1095 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Aso et al.: "Synthetic studies and properties of N-tert-butylaminoxyl nucleosides"Nucleic Acids Research Supplement. 3. 9-10 (2003)

    • Related Report
      2003 Annual Research Report

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Published: 2003-04-01   Modified: 2016-04-21  

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