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Development of Solvent-induced Chirality Switching Resolution Method

Research Project

Project/Area Number 16K17888
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Functional solid state chemistry
Research InstitutionSaitama University

Principal Investigator

KODAMA KOICHI  埼玉大学, 理工学研究科, 准教授 (90509712)

Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2018: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywords光学分割 / 有機結晶 / キラリティー / 不斉認識 / 水素結合 / ジアステレオマー塩 / ホスフィン酸 / 溶媒効果 / 結晶工学 / 分子認識 / 超分子化学
Outline of Final Research Achievements

We have investigated the scope of chiral carboxylic acids in the solvent-induced chirality switching optical resolution. It was found that mandelic acids with a halogen substituent on the meta position could be enantioseparated and their stereochemistry was changed dependent on the used crystallization solvents. Based on the results of crystallographic analysis of the diastereomeric salts, it was suggested that the incorporation of the solvent in the salt with hydrogen bonds changed the stability of each salt, which resulted in the switching of chirality of the deposited salts.

Academic Significance and Societal Importance of the Research Achievements

医薬品の原料などとして光学活性化合物の需要は高く、より効率的で経済的な生産法の開発が強く望まれている。本研究成果は従来法と比較して光学活性化合物の生産におけるプロセス数を削減することができる方法を提供するものであり、今後のさらなる検討によって、社会において需要の高い化合物にも適用できるようになることが期待される。また、三種類以上の化合物からの共結晶化現象は学術的にも注目されており、機能性超分子の開発や薬物特性のコントロールなどに応用されることが期待される。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (4 results)

All 2018 2017

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

  • [Journal Article] Solvent-induced chirality switching in the enantioseparation of regioisomeric hydroxyphenylpropionic acids via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol2017

    • Author(s)
      Koichi Kodama, Jun Nagata, Nobuhiro Kurozumi, Hiroaki Shitara and Takuji Hirose
    • Journal Title

      Tetrahedron: Asymmetry

      Volume: 28 Issue: 3 Pages: 460-466

    • DOI

      10.1016/j.tetasy.2017.02.011

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 2-ヒドロキシ-4-フェニル酪酸の光学分割における溶媒による立体の逆転現象2018

    • Author(s)
      易猛・廣瀬卓司・小玉康一
    • Organizer
      日本化学会 第8回CSJ化学フェスタ2018
    • Related Report
      2018 Annual Research Report
  • [Presentation] Chiral Organic Salt-Based Supramolecular Hosts for Enantioselective Inclusion of Neutral Guest Compounds2017

    • Author(s)
      Koichi Kodama
    • Organizer
      日本化学会第97春季年会 アジア国際シンポジウム
    • Place of Presentation
      慶應義塾大学(神奈川県横浜市)
    • Year and Date
      2017-03-17
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] ハロゲン置換マンデル酸の光学分割における溶媒による立体の逆転現象2017

    • Author(s)
      川崎 梢・塚本香毬耶・廣瀬卓司・小玉康一
    • Organizer
      日本化学会 第7回CSJ化学フェスタ2017
    • Related Report
      2017 Research-status Report

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Published: 2016-04-21   Modified: 2020-03-30  

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