• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Studies toward development of a novel CTZ-type hydrogen sulfide probe

Research Project

Project/Area Number 26560443
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Chemical biology
Research InstitutionTokyo Medical and Dental University

Principal Investigator

Hosoya Takamitsu  東京医科歯科大学, 生体材料工学研究所, 教授 (60273124)

Project Period (FY) 2014-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥3,640,000 (Direct Cost: ¥2,800,000、Indirect Cost: ¥840,000)
Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2014: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsケミカルバイオロジー / 有機合成化学 / アジド / ピラジン / セレンテラジン / 化学プローブ / 生物発光 / イメージング / ルシフェリン
Outline of Final Research Achievements

We aimed to develop a new method that is capable of detecting hydrogen sulfide with a novel coelenterazine (CTZ)-type probe. To achieve this purpose, we conducted following studies regarding the synthesis of CTZ-related compounds and reactivities of azide molecules. (1) A novel synthetic method for v-coelenterazine (v-CTZ), which is a vinylene-bridged analog of native CTZ with a large red-shifted luminescence property, has been developed. The synthesis was achieved in a concise way through the use of three sequential cross-coupling reactions and ring-closing metathesis (RCM). (2) We have found that four different substituents can be introduced into pyrazine via four palladium-catalyzed regioselective cross-coupling reactions, using trihalogenated aminopyrazine as the starting material. (3) We have revisited the reduction of azides using a variety of phosphines and achieved a selective reduction of an aromatic azido group under mild conditions.

Report

(3 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • Research Products

    (3 results)

All 2016 2015

All Journal Article (1 results) (of which Peer Reviewed: 1 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (2 results)

  • [Journal Article] Concise Synthesis of v‐Coelenterazines2015

    • Author(s)
      Takamitsu Hosoya, Rie Iimori, Suguru Yoshida, Yuto Sumida, Yuiko Sahara-Miura, Jun-ichi Sato, Satoshi Inouye
    • Journal Title

      Organic Letters

      Volume: 17 Issue: 15 Pages: 3888-3891

    • DOI

      10.1021/acs.orglett.5b01872

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] クロスカップリング反応により4つの置換基を自在に導入可能なピラジン合成法の開発2016

    • Author(s)
      秋山 圭、西山義剛、吉田 優、細谷孝充
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 4度のクロスカップリング反応を利用した4置換ピラジン合成法の開発2015

    • Author(s)
      秋山 圭、西山義剛、吉田 優、細谷孝充
    • Organizer
      第5回CSJ化学フェスタ2015
    • Place of Presentation
      タワーホール船堀(東京都江戸川区)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Annual Research Report

URL: 

Published: 2014-04-04   Modified: 2017-05-10  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi