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Quantitative detection of chirality by chiral mass spectrometry on the basis of molecular recognition chemistry

Research Project

Project/Area Number 18K05095
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 33010:Structural organic chemistry and physical organic chemistry-related
Research InstitutionOsaka Research Institute of Industrial Science and Technology

Principal Investigator

Shizuma Motohiro  地方独立行政法人大阪産業技術研究所, 森之宮センター, 総括研究員 (40416318)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2020: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2019: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2018: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywordsキラリティー / 質量分析 / 分子認識 / 安定同位体標識 / 光学純度決定
Outline of Final Research Achievements

The purpose of this study is chiral analysis by mass spectrometry only.  In this study, chiral polyether hosts and chiral copper complexes were designed and synthesized to discrimine the chirality of chiral ammnonium ions and amino acids, respectively. Further, their enantiomer hosts labeled with deuterium atoms were synthesized. The pair of the labeled/unlabeled host were used after adding the guest mixture to estimate the enantiomeric excess of the multiple guests simultaneously, easily and quickly based on the relative peak intensity of the labeled/unlabeled host-guest complex ions by mass spectrometry only.

Academic Significance and Societal Importance of the Research Achievements

近年、生体内のD-アミノ酸がさまざまな疾病と関連していることやあるいは有用な作用をしていることなどが見いだされており、高感度で簡便なキラル評価方法が希求されている。本研究成果はこれらに対して高感度分析法である質量分析のみで迅速にキラル評価を行える手法を提案できた。また、分子間の相互作用およびイオン化部位の制御により質量分析でキラル評価ができるホスト-ゲスト系の分子設計について一つの指針を見出すことができた。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (10 results)

All 2020 2019 2018

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Open Access: 1 results) Presentation (7 results) (of which Int'l Joint Research: 1 results,  Invited: 1 results)

  • [Journal Article] Enantioselectivity-Evaluation of Chiral Copper(II) Complexes Coordinated by Novel Chiral Tetradentate Ligands for Free Amino Acids by Mass Spectrometry Coupled With the Isotopically Labeled Enantiomer Method2020

    • Author(s)
      Nakakoji Takashi、Yoshino Kaori、Izutsu Kazuki、Sato Hirofumi、Miyake Hiroyuki、Mieda Eiko、Shinoda Satoshi、Tsukube Hiroshi、Kawasaki Hideya、Arakawa Ryuichi、Ono Daisuke、Shizuma Motohiro
    • Journal Title

      Frontiers in Chemistry

      Volume: 8 Pages: 1-10

    • DOI

      10.3389/fchem.2020.598598

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Mass spectrometric detection of enantioselectivity in three-component complexation, copper(II)-chiral tetradentate ligand-free amino acid in solution2020

    • Author(s)
      T. Nakakoji, H. Sato, D. Ono, H. Miyake, S. Shinoda, H. Tsukube, H. Kawasaki, R. Arakawa, M. Shizuma
    • Journal Title

      ChemComm

      Volume: 56 Issue: 1 Pages: 54-57

    • DOI

      10.1039/c9cc07231d

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] 非共有結合型錯イオン形成挙動と糖類の異性体識別2018

    • Author(s)
      靜間基博
    • Journal Title

      J. Mass Spectrom. Soc. Jp.

      Volume: 66 Pages: 190-196

    • NAID

      130007498082

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] 高速原子衝撃質量分析による非環状キラルホストのキラルアンモニウムイオンに対するキラル識別能評価と錯安定度定数決定2020

    • Author(s)
      靜間基博、鈴木健之、朝野芳織、松崎剛、川野真太郎、佐藤博文、小野大助
    • Organizer
      第68回質量分析総合討論会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 有機金属イオンを用いたアミノ酸に対するキラル認識2019

    • Author(s)
      中小路崇、佐藤博文、篠田哲史、川崎英也、荒川隆一、三宅弘之、○靜間基博
    • Organizer
      第8回イオン移動度研究会/第72回イオン反応研究会 合同講演会
    • Related Report
      2019 Research-status Report
  • [Presentation] キラル配位子を有する銅錯イオンへの配位挙動を利用したナノエレクトロスプレー質量分析によるアミノ酸の光学異性一斉検出2019

    • Author(s)
      中小路崇、三宅弘之、篠田哲史、松崎剛、朝野芳織、鈴木健之、佐藤博文、靜間基博
    • Organizer
      第67回質量分析総合討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] 質量分析法を活用 質量分析法を活用 した光学活性銅錯体のキラルアミノ酸識別能評価2019

    • Author(s)
      中小路崇、佐藤博文、川崎英也、荒川隆一、篠田哲史、三宅弘之、靜間基博
    • Organizer
      モレキュラー・キラリティー シンポジウム
    • Related Report
      2019 Research-status Report
  • [Presentation] 質量分析によるキラリティー検出法2019

    • Author(s)
      〇靜間基博
    • Organizer
      第3回オレオマテリアル学術交流会
    • Related Report
      2019 Research-status Report
    • Invited
  • [Presentation] Chirality Detection by Mass Spectrometry Coupled with the Isotopically Labeled Method on the Basis of Molecular Recognition Chemistry2019

    • Author(s)
      Motohiro Shizuma
    • Organizer
      BIT’s 7th Annual Conference of AnalytiX-2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] 高速原子衝撃質量分析による化学修飾フルクトオリゴ糖類のキラルアミノ酸エステルアンモニウムイオンに対するキラル識別能評価2018

    • Author(s)
      ○靜間基博、佐藤博文、川野真太郎、松崎剛、朝野芳織、鈴木健之、小野大助
    • Organizer
      日本油化学会第57回年会
    • Related Report
      2018 Research-status Report

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Published: 2018-04-23   Modified: 2022-01-27  

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