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2013 Fiscal Year Final Research Report

Development and biological application of sulfo-click type reactions

Research Project

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Project/Area Number 23390024
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Drug development chemistry
Research InstitutionUniversity of Toyama

Principal Investigator

HATANAKA Yasumaru  富山大学, 事務局, 理事・副学長 (30111181)

Co-Investigator(Kenkyū-buntansha) CHIBA Junya  富山大学, 大学院・医学薬学研究部(薬学), 助教 (50436789)
Project Period (FY) 2011-04-01 – 2014-03-31
Keywordsクリック反応 / ケミカルバイオロジー / チオカルボン酸 / チオアミド / スルホニルアジド
Research Abstract

The chemical biology of sulfo-click type reactions was examined in this project. During the course of project, a novel click type reaction was discovered. The common sulfo-click reaction couples a thioacid to a sulfonyl azide to give a sulfonamide, whereas the new reaction is able to couple a thioamide to a sulfonyl azide under mild conditions resulting an amidine product. Since the reaction proceeds smoothly in water without catalysts or promoters, the application of this reaction was also examined. Using two sulfo-click type reactions, various derivatives of bioactive compounds such as sugars, amino acids, and medicines were developed.

  • Research Products

    (15 results)

All 2014 2013 2012 2011 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results) Presentation (10 results) Remarks (1 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] Coupling reaction of thioamides with sulfonyl azides : An efficient catalyst-free click-type ligation under mild conditions2013

    • Author(s)
      Muhammad Aswad, Junya Chiba, Takenori Tomohiro and Yasumaru Hatanaka
    • Journal Title

      Chem. Commun

      Volume: 49 Pages: 10242-10244

    • DOI

      10.1039/C3CC46055J

    • Peer Reviewed
  • [Journal Article] Photoaffinity casting of a coumarin flag for rapid identification of ligand-binding sites within protein2013

    • Author(s)
      Shota Morimoto, Takenori Tomohiro, Nobuyuki Maruyama and Yasumaru Hatanaka
    • Journal Title

      Chem. Commun

      Volume: 49 Pages: 1811-1813

    • DOI

      10.1039/c3cc38594a

    • Peer Reviewed
  • [Presentation] 光アフィニティーラベリングの画期的高速化と生命科学上のブレークスルーへの応用(学会賞受賞講演)2014

    • Author(s)
      畑中 保丸
    • Organizer
      日本薬学会第134回年会
    • Place of Presentation
      熊本市
    • Year and Date
      20140327-30
  • [Presentation] C1 位カルボキシ基の誘導化によるシアル酸アナローグの開発2014

    • Author(s)
      中山 純, 橋田 まみ, 志村 みさき, 千葉順哉, 友廣 岳則, 畑中 保丸
    • Organizer
      日本薬学会第134回年会
    • Place of Presentation
      熊本市
    • Year and Date
      20140327-30
  • [Presentation] 多機能光アフィニティープローブによるタンパク質機能構造の効率的解析(学会賞受賞講演)2013

    • Author(s)
      畑中 保丸
    • Organizer
      第35回日本光医学・光生物学会
    • Place of Presentation
      浜松市
    • Year and Date
      20130712-13
  • [Presentation] A Mild Coupling of Thioamide and Sulfonylazide as a Novel Click Reaction without Activation Additives2013

    • Author(s)
      Muhammad Aswad, 加藤 日奈, 中山 純, 千葉 順哉, 友廣 岳則, 畑中 保丸
    • Organizer
      日本ケミカルバイオロジー学会第8回年会
    • Place of Presentation
      文京区
    • Year and Date
      20130619-21
  • [Presentation] Photochemical Casting of a Fluorophore Concomitant with a Cleavable Photoaffinity Cross-Liking2013

    • Author(s)
      Takenori Tomohiro, Shota Morimoto and Yasumaru Hatanaka
    • Organizer
      The 23rd French-Japanese Symposium on Medicial and Fine Chemistry
    • Place of Presentation
      Nagasaki
    • Year and Date
      20130512-15
  • [Presentation] チオアミドを利用した水中での無触媒クリック型反応2013

    • Author(s)
      千葉 順哉, 畑中 保丸
    • Organizer
      平成25年度中部地区医療・バイオ系シーズ発表会
    • Place of Presentation
      名古屋市
    • Year and Date
      2013-12-12
  • [Presentation] 発蛍光性クロスリンカーを利用したターゲットタンパク質の選択的精製と構造解析への応用2012

    • Author(s)
      友廣 岳則, 森本 正大, 畑中 保丸
    • Organizer
      第34回日本光医学・光生物学会
    • Place of Presentation
      神戸市
    • Year and Date
      20120727-28
  • [Presentation] Bioisosteric approach for development of multifunctional bio-probes2011

    • Author(s)
      Junya Chiba, Hitomi An-yo and Yasumaru Hatanaka
    • Organizer
      IUPAC 7th International Conference on Novel Materials and Synthesis
    • Place of Presentation
      Shanghai (China)
    • Year and Date
      20111016-21
  • [Presentation] N-アセチルノイラミン酸のアニオン部位近傍に光反応基を有する光プローブの開発2011

    • Author(s)
      星野 直人, 山根 まどか, 友廣 岳則, 畑中 保丸
    • Organizer
      第30回日本糖質学会年会
    • Place of Presentation
      長岡市
    • Year and Date
      20110711-13
  • [Presentation] Synthesis of multifunctional diazirine probes and their application in the chemical biology2011

    • Author(s)
      Takenori Tomohiro and Yasumaru Hatanaka
    • Organizer
      The 5th International Symposium on Aliphatic Compounds
    • Place of Presentation
      St. Petersburg (Russia)
    • Year and Date
      20110606-07
  • [Remarks]

    • URL

      http://www.pha.u-toyama.ac.jp/laboratory/anachem/index.html

  • [Patent(Industrial Property Rights)] 2-デオキシ-2, 3-ジデヒドロシアル酸誘導体およびその製造法2013

    • Inventor(s)
      畑中 保丸, 千葉 順哉, 友廣 岳則, 中山 純
    • Industrial Property Rights Holder
      富山大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      特願 2013-236357
    • Filing Date
      2013-11-15
  • [Patent(Industrial Property Rights)] スルホニルアジド誘導体およびアシルスルホンアミド誘導体の製造方法並びにそれらの利用2013

    • Inventor(s)
      畑中 保丸, 千葉 順哉, 友廣 岳則
    • Industrial Property Rights Holder
      富山大学
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      特願 2013-089114
    • Filing Date
      2013-04-22

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Published: 2015-06-25  

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