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Katoono Ryo

Faculty of Science　Chemistry　Organic and Biological ChemistryAssistant Professor

Researcher basic information

■ Degree
  • 博士（理学）, 北海道大学
■ URL
researchmap URLホームページURL■ Various IDs
Researcher number
  • 60432142
J-Global ID■ Research Keywords and Fields
Research Keyword
  • Terephthalamide
  • macrocycle
  • triple bond
  • chiral chemistry
Research Field
  • Life Science, Bioorganic chemistry, Physical organic chemistry, Chiral chemistry
  • Nanotechnology/Materials, Structural organic chemistry and physical organic chemistry, Physical organic chemistry, Chiral chemistry
■ Educational Organization

Career

■ Career
Career
  • Nov. 2021 - Present
    Hokkaido University, 大学院理学研究院国際理学連携教育センター, 助教
  • Nov. 2011 - Oct. 2021
    Hokkaido University, Department of Chemistry, Faculty of Science, 助教
  • Apr. 2006 - Oct. 2011
    JAIST, School of Materials Science, 助教

Research activity information

■ Papers
■ Books and other publications
  • Ch 14: Design of chirality-sensing systems based on supramolecular transmission of chirality. In Nabeshima, T. (Eds) Synergy in Supramolecular Chemistry.
    Ryo Katoono, pp. 247-260
    CRC press, 2015, [Joint work]
■ Affiliated academic society
  • THE CHEMICAL SOCIETY OF JAPAN
■ Research Themes
  • 多元的動的キラル空間におけるキラル増幅"
    科学研究費助成事業
    01 Apr. 2021 - 31 Mar. 2024
    上遠野 亮
    本研究では、"キラル増幅"の新たな一面を提示する。それは、ラセミ化できるキラル構造が同一分子内で連続して多元的に配置された場合、個々のねじれ優先性が自発的に増大する現象として独自に定義した。結果として、個々のキラリティは動的であるにもかかわらず、自発的に高められたホモキラリティによって、特定のキラル構造が支配的に存在するようになるだろう。そのような分子は、立体化学が安定なキラル化合物に匹敵する分子とみなすことができる。
    具体的には、二つの分子群を足場として実証する：動的な８の字キラリティを有するマクロサイクルを（I）積層または（II）縮環により集積し、それぞれ多元的な動的キラル空間を創出する。後者は、このキラル増幅現象を定量的に観測することを期待するものである。明確な分子構造を足場とする光学活性の定量的な観測は、巨大分子系におけるキラル分子の形状と光学活性との間の関係性を考察するのに資することが期待できる。
    本年度は、テーマI：キラルな三層構造の合成および光学分割を完了した。四層構造についても合成および光学分割を完了した。四層構造は、形式的に二つの構造を想定しうるが、目的としたキラルな四層構造に対する選択的合成を達成した。光学分割については、一方のエナンチオマーのみ純粋に単離することができた。隣接する動的キラル空間で、互いのねじれ優先性を協同的に打ち消し合うモデル分子として二層構造も合成した。この合成検討を通じて、三層および四層構造の合成経路を確立できた。二、三四層それぞれ純粋に得られた光学活性体について、旋光度および円二色性を測定した。テーマII：ラセミ化できるマクロサイクルの環状五量体および六量体の合成を完了した。環化前駆体の配座的動的特性について一部完全に理解することは断念したが、概ね合成経路を確立したと言える。
    日本学術振興会, 基盤研究(C), 北海道大学, 21K05031
  • Chiroptical properties based on the assembly of achiral phenylacetylene macrocycles (PAMs)
    Grants-in-Aid for Scientific Research
    01 Apr. 2018 - 31 Mar. 2021
    KATOONO RYO
    Newly-designed chiral molecules and their chiroptical properties were studied. Here, two achiral rings create chirality through the assembly, such as stacking, mechanical linking, or merging. As an achiral ring, a phenylacetylene macrocycle ([6]PAM) was used for the creation of multiple chiral molecules. Site-specific modification of PAMs was suitable for bridging of the two rings at arbitrary positions.
    Regarding the chiroptical properties, the specific optical rotation of a mechanical bound molecule was outstanding (>±1000), and also molar CDs (Δε) exceeded at most ±1000 in the CD spectroscopy. It is interesting to note that another mechanical bound molecule, with the same component but bridged at different positions, showed only halves of those activities. For [11]PAM, these activities were worse. These results shows that chiroptical properties could be modulated by the shape of a molecule.
    Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (C), Hokkaido University, 18K05069
  • Unimolecular n-bit memory and molecular wire with variable resistivities: Proposal of new molecular design and prototype construction
    Grants-in-Aid for Scientific Research
    01 Apr. 2015 - 31 Mar. 2020
    Takanori Suzuki
    The dynamic redox (dyrex) systems undergo reversible bond formation/cleavage upon electron transfer. This characteristic feature provides those redox systems with electrochemical bistability, by which oxidation of the donor and reduction of the cationic species occur at difference potentials. Such separation prevents the exchange of electrons between the neutral state and the cationic state, whereas the activation energy for the corresponding process in ordinary redox pairs is negligible. Thus, bistability in dynamic redox pairs can lead to their use in unimolecular memory because one molecule can be considered to be one digit if the two redox states are assigned values of 0 and 1 (e.g., the neutral donor is 0 and the cationic state is 1). We have developed several promising dyrex systems in this work, which would be used as prototypes for developing advanced molecular memory unit.
    Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (B), Hokkaido University, 15H03790
  • Fused oligomers of a macrocycle with dynamic figure eight chirality
    Grants-in-Aid for Scientific Research
    01 Apr. 2015 - 31 Mar. 2018
    Katoono Ryo; TANAKA Yuki; KAWAI Shunsuke; KUSAKA Keiichi; OBARA Yudai
    I have newly designed a series of fused oligomers of macrocycles with dynamic figure eight chirality. Dynamic features in solution of these fused oligomers were investigated through NMR, UV and CD spectroscopy.
    For fused oligomers, the barrier to dynamic interconversion between two helical conformations with M- or P-helicity followed a specific pattern similar to that of the original unit of a macrocycle. Complexation and chiroptical properties were dependent on the molecular shape, that is a manner of fusion. We found a new perspective on "chiral amplification". In a fused trimer or a tetramer, the helical-sense preference increased with the number of units. These finding was brought about by quantitative observation of the helical-sense preferences through NMR spectroscopy in solution.
    Japan Society for the Promotion of Science, Grant-in-Aid for Young Scientists (B), Hokkaido University, 15K17818
  • Design and control of dynamic propeller chirality based on terephthalamides
    Grants-in-Aid for Scientific Research
    01 Apr. 2013 - 31 Mar. 2015
    KATOONO Ryo
    We have designed and synthesized dynamic molecules with propeller chirality based on a terephthalamide skeleton. The two amide groups in a terephthalamide unit acted as a binding site for caputuring a ditopic guest through the formation of hydrogen bonds, and contributed to creation of chiroptical signals when the guest was chiral, or a chiral auxiliary was attached to the terephthalamide unit(s).
    We have demonstrated chiroptical signals based on dynamic molecular propellers.
    In a complexed state, a particular sense of dynamic propeller chirality was predominantly favored over the other, and exhibited chiroptical signals.
    Japan Society for the Promotion of Science, Grant-in-Aid for Young Scientists (B), Hokkaido University, 25810017
  • Modulation of cellular metabolism based on controlling the mobility of multivalent ligands using stimuli-responsive polyrotaxanes
    Grants-in-Aid for Scientific Research
    2007 - 2010
    YUI Nobuhiko
    In order to aim at controlling cellular response via stimuli-responsive polyrotaxanes, the preparation of a variety of polyrotaxanes, the characterization of their properties, and the protein and cellular responses to these polyrotaxanes were performed. Macromolecular inclusion of loose-fit polyrotaxane, temperature-responsive polyrotaxane formation, enhanced binding of mannose-conjugated polyrotaxane with specific protein, and the production of anti-inflammatory cytokine from macrophages were clarified in this study.
    Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (B), Japan Advanced Institute of Science and Technology, 19300170
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