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Development of high efficient synthesis method of selenium neucleosides and its application

Research Project

Project/Area Number 15K07856
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionGifu University

Principal Investigator

KOKETSU Mamoru  岐阜大学, 工学部, 教授 (50178208)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords核酸 / セレン元素 / アミノ酸 / セレン導入試薬 / セレノグルタチオン / アデノシル-セレノメチオニン / セレン修飾ウリジン / セレニウム / 保護基 / セレノシステイン
Outline of Final Research Achievements

In recent years, selenium-containing biomolecules have been documented as promising pharmacological agents. We initially explored an efficient method for the synthesis of 5’-selenium modified nucleosides based on the idea of direct functionalization of 2-(trimethylsilyl)ethyl (TSE) selenyl groups. This method was successfully applied to the synthesis of highly functionalized nucleoside, Se-adenosyl-L-selenomethionine (SeAM). In addition, we developed a valuable route for the synthesis of 2’-alkylselenouridine derivatives via a 2-(trimethylsilyl)ethylselenation approach. Furthermore, we applied the 2-TSE selenyl group to the synthesis of selenium-containing amino acid derivatives including biologically important selenocysteine (Sec) and selenoglutathione (GSeH) derivatives. Our findings highlight the great utility and versatility of the 2-TSE selenyl group as a selenating reagent into biomolecules.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (5 results)

All 2017 2016 2015 Other

All Int'l Joint Research (1 results) Journal Article (4 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 4 results,  Acknowledgement Compliant: 3 results)

  • [Int'l Joint Research] ユタ大学(米国)

    • Related Report
      2015 Research-status Report
  • [Journal Article] Application of bis-2-(trimethylsilyl)ethyl diselenide to the synthesis of selenium-containing amino acid derivatives2017

    • Author(s)
      Yonezawa Tsubasa、Yamaguchi Masahito、Ninomiya Masayuki、Koketsu Mamoru
    • Journal Title

      Tetrahedron

      Volume: 73 Issue: 42 Pages: 6085-6091

    • DOI

      10.1016/j.tet.2017.09.004

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Preparation of 2'-alkylselenouridine derivatives via a 2-(trimethylsilyl)ethylselenation approach2017

    • Author(s)
      Shota Fukuno, Masayuki Ninomiya and Mamoru Koketsu
    • Journal Title

      Synlett

      Volume: 28 Pages: 831-834

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] An efficient synthesis of 2-selenouridine and its phosphoramidite precursor2016

    • Author(s)
      Masakazu Kogami, Darrell R. Davis and Mamoru Koketsu
    • Journal Title

      Heterocycles

      Volume: 92 Issue: 1 Pages: 345-348

    • DOI

      10.3987/com-15-13349

    • NAID

      40020725402

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] An efficient method for the synthesis of selenium modified nucleosides: Its application to the synthesis of Se-adenosyl-L-selenomethionine (SeAM)2015

    • Author(s)
      Masakazu Kogami and Mamoru Koketsu
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 13 Issue: 36 Pages: 9405-9417

    • DOI

      10.1039/c5ob01316j

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant

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Published: 2015-04-16   Modified: 2022-01-24  

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