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Development of determination method of absolute configuration using binaphthyl CD probe and its application to natural products

Research Project

Project/Area Number 23590027
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

HOSOI shinzo  京都薬科大学, 薬学部, 教授 (60209236)

Co-Investigator(Kenkyū-buntansha) KATSUMOTO Yukiteru  広島大学, 大学院・理学研究科, 助教 (90351741)
Project Period (FY) 2011 – 2013
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2012: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2011: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords誘起円二色性 / ビナフチル / 絶対配置決定法 / キラルアミン / 立体配座解析 / ステロール / 天然物 / キラル二級アルコール / 円二色性 / CDプローブ / 絶対配置決定 / アシルシアニド / 誘起CD
Research Abstract

The induced circular dichroism (ICD) method was proven to be practical and applicable to natural products: 1) various types of unsaturated sterols were hydrogenated to give saturated sterols. As a result, CD spectra of the binaphthyl derivatives of the saturated sterols showed bisignate curves centered at 240 nm (3S: positive chirality; 3R: negative one). This should contribute significantly to the analysis of metabolites of various types of sterols. 2) a novel CD chromophoric agent having two reaction sites was designed and applied to chiral secondary alcohols. The intensity of Cotton effects was found to be twice more than that of the monoester. 3) its application to D, L-cycloserines was examined: D-cycloserine derivative with an (R)-configuration showed positive exciton chirality whereas the L-cycloserine derivative with an (S)-configuration exhibited a negative one. It will be a powerful tool to determine the absolute configurations of various natural products with an amino group.

Report

(4 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • 2012 Research-status Report
  • 2011 Research-status Report
  • Research Products

    (9 results)

All 2013 2012 Other

All Journal Article (3 results) (of which Peer Reviewed: 1 results) Presentation (6 results)

  • [Journal Article] Novel approach to determining the absolute configurations at the C3-positions of various types of sterols based on an induced circular dichroism2012

    • Author(s)
      Toshio Fujiwara, Yuka Taniguchi, Yukiteru Katsumoto, Takeyuki Tanaka, Minoru Ozeki, Hiroki Iwasaki, Manabu Node, Masayuki Yamashita, Shinzo Hosoi
    • Journal Title

      Steroids

      Volume: 77 Pages: 1198-1204

    • Related Report
      2013 Final Research Report 2012 Research-status Report
  • [Journal Article] Induced circular dichroism in chiral N-methyl amides possessing an achiral binaphthyl chromophore and its application to absolute configuration determination of aliphatic chiral amines2012

    • Author(s)
      Toshio Fujiwara, Yuka Taniguchi, Yukiteru Katsumoto, Takeyuki Tanaka, Manabu Node, Minoru Ozeki, Masayuki Yamashita, Shinzo Hosoi
    • Journal Title

      Tetrahedron : Asymmetry

      Volume: 23 Pages: 981-991

    • Related Report
      2013 Final Research Report
  • [Journal Article] Induced circular dichroism in chiral N-methyl amides possessing an achiral binaphthyl chromophore and its application to absolute configuration determination of aliphatic chiral amines2012

    • Author(s)
      Toshio Fujiwara, Yuka Taniguchi, Yukiteru Katsumoto, Takeyuki Tanaka, Manabu Node, Minoru Ozeki, Masayuki Yamashita, Shinzo Hosoi
    • Journal Title

      Tetrahedron: Asymmetry

      Volume: 23 Issue: 13 Pages: 981-991

    • DOI

      10.1016/j.tetasy.2012.06.013

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] ビナフチル型新規CD発色試薬の開発とキラル第二級アルコールの絶対配置決定法への応用2013

    • Author(s)
      河野大貴,冨士原聡夫,谷口由佳,村木加愉子,國立悠里,馬場ゆうみ,岩﨑宏樹,小島直人,細井信造,山下正行
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Year and Date
      2013-03-28
    • Related Report
      2013 Final Research Report
  • [Presentation] 新規CD発色試薬のキラル第二級アルコールの絶対配置決定法への応用2012

    • Author(s)
      冨士原聡夫、谷口由佳、村木加愉子、河野大貴、國立悠里、馬場ゆうみ、岩崎宏樹、小島直人、細井信造、山下正行
    • Organizer
      第62回日本薬学会近畿支部総会・大会
    • Place of Presentation
      西宮
    • Year and Date
      2012-10-20
    • Related Report
      2013 Final Research Report
  • [Presentation] 誘起円二色性を基盤とするステロール類の3位水酸基の絶対配置決定について2012

    • Author(s)
      冨士原聡夫、谷口由佳、岩崎宏樹、細井信造、山下正行
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      札幌
    • Year and Date
      2012-03-29
    • Related Report
      2013 Final Research Report
  • [Presentation] 新規CD発色試薬のキラル第二級アルコールの絶対配置決定法への応用

    • Author(s)
      冨士原聡夫、細井信造
    • Organizer
      第62回日本薬学会 近畿支部総会・大会
    • Place of Presentation
      武庫川女子大学(西宮)
    • Related Report
      2012 Research-status Report
  • [Presentation] ビナフチル型新規CD発色試薬の開発とキラル第二級アルコールの絶対配置決定

    • Author(s)
      冨士原聡夫、細井信造
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      パシフィコ横浜(横浜)
    • Related Report
      2012 Research-status Report
  • [Presentation] 誘起円二色性を基盤とするステロール類の3位水酸基の絶対配置決定について

    • Author(s)
      細井信造
    • Organizer
      日本薬学会第132年会
    • Place of Presentation
      北海道大学(北海道)
    • Related Report
      2011 Research-status Report

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Published: 2011-08-05   Modified: 2019-07-29  

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