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Establishment of practical determination method of absolute configuration based on induced circular dichroism and quantum chemical approach to elucidation of its origin

Research Project

Project/Area Number 26460019
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) 山下 正行  京都薬科大学, 薬学部, 教授 (20239982)
勝本 之晶  福岡大学, 理学部, 准教授 (90351741)
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywords誘起円二色性 / ビナフチル / 絶対配置決定法 / ステロール / デカリン / 発色団 / 立体選択的合成 / キラリティー / 絶対配置決定 / ステロイド / ロドデノール / フェニルアルコール
Outline of Final Research Achievements

In order to enlarge the versatility of “the induced exciton coupled circular dichroism method”, we have carried out the followings. 1) The twelve chiral stereoisomers of 2-naphthalenols were prepared and the CD spectra of the corresponding binaphthyl esters were obtained. For the six stereoisomers of decahydro-4a-methyl-2-naphthalenol, the CD spectra of the binaphthyl ester derivatives show the bisignate CD signal with an expected sign, in which the positive for 2S-isomer and the negative for 2R-isomer. However, the other two isomers give rise to an opposite signal to the expectation, 2) We have applied this method to determine the absolute configuration of rhododenol, which has the melanogenesis suppressing activity. The CD spectra of the rhododenol derivatives have shown a split CD, indicating the potential application of the method proposed here.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (4 results)

All 2017 2016 2015 2014

All Presentation (4 results)

  • [Presentation] ビナフチル型CD発色試薬によるdecahydro-4a-methyl-2-naphthalenol類の誘導体化およびそれらのCDスペクトルの挙動について2017

    • Author(s)
      山西 光咲、小森 沙織、箙 由布子、國立 悠里、馬場 ゆうみ、河野 大貴、山下 正行、小島 直人、岩﨑 宏樹、細井 信造
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台国際センター(仙台)
    • Year and Date
      2017-03-25
    • Related Report
      2016 Annual Research Report
  • [Presentation] 美白成分ロドデノールの誘起CD励起子法による絶対配置決定法2016

    • Author(s)
      篠 佳秀、細井信造、岡本恭輔、岩崎宏樹、小島直人、山下正行
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      パシフィコ横浜(横浜)
    • Year and Date
      2016-03-28
    • Related Report
      2015 Research-status Report
  • [Presentation] ビナフチル型CD発色試薬の改良合成法について2015

    • Author(s)
      岡本恭輔、箙 由布子、細井信造、小島直人、岩﨑宏樹、山下正行
    • Organizer
      第65回日本薬学会近畿支部総会・大会
    • Place of Presentation
      大阪大谷大学(大阪)
    • Year and Date
      2015-10-17
    • Related Report
      2015 Research-status Report
  • [Presentation] 誘起CD励起子法によるステロール類の3位水酸基の絶対配置決定2014

    • Author(s)
      岡本恭輔、本光由佳梨、山下正行、小島直人、岩﨑宏樹、細井信造
    • Organizer
      第64回日本薬学会 近畿支部総会・大会
    • Place of Presentation
      京都薬科大学(京都)
    • Year and Date
      2014-10-11
    • Related Report
      2014 Research-status Report

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Published: 2014-04-04   Modified: 2018-03-22  

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