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Development of structural analysis methods for middle-sized and polar molecules by VCD spectroscopy

Research Project

Project/Area Number 18H02093
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Review Section Basic Section 37020:Chemistry and chemical methodology of biomolecules-related
Research InstitutionHokkaido University

Principal Investigator

Taniguchi Tohru  北海道大学, 先端生命科学研究院, 講師 (00587123)

Project Period (FY) 2018-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥17,550,000 (Direct Cost: ¥13,500,000、Indirect Cost: ¥4,050,000)
Fiscal Year 2021: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2020: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Fiscal Year 2019: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2018: ¥9,750,000 (Direct Cost: ¥7,500,000、Indirect Cost: ¥2,250,000)
Keywords円二色性 / 構造決定 / 中分子 / 柔軟分子 / 理論計算 / カルボジイミド
Outline of Final Research Achievements

Middle-sized natural products (M.W. 500 to 2000) such as oligosaccharides, cyclic peptides, macrolides, and other metabolites are promising drug candidates beyond Lipinski’s rule of 5. Because middle-sized molecules target, for example, protein-protein interactions more efficiently than small molecules do, a large number of such drugs have been approved and under development in recent years. For the exploration of such natural products and their synthetic derivatives, their structural elucidation is one of the major bottlenecks as they possess multiple chiral centers. In this work, we developed new methods for structural analysis of middle-sized molecules by using vibrational circular dichroism (VCD) spectroscopy. Furthermore, this work achieved the first preparation of carbodiimides with one-handed axial chirality.

Academic Significance and Societal Importance of the Research Achievements

本研究ではこれまで構造分析が困難だった中分子や、脂質のような柔軟分子、糖のような高極性分子などを簡便に構造決定する新たな方法論を提供した。本研究成果は、中分子を始めとする各種分子の構造決定というボトルネックを解消し、それらの研究が出口とする医薬・農薬創製に資すると期待される。
さらに、1932年に提唱されてから86年間入手されてこなかった「片方のみの軸不斉を有するカルボジイミド」の合成に成功した。カルボジイミドは工業的に世界で最も汎用される分子であり、その基本的な性質を解明は今後の化学工業への波及効果が期待される。

Report

(5 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Annual Research Report
  • 2019 Annual Research Report
  • 2018 Annual Research Report
  • Research Products

    (23 results)

All 2022 2021 2019 2018 2016 Other

All Int'l Joint Research (2 results) Journal Article (14 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 14 results,  Open Access: 1 results) Presentation (7 results) (of which Int'l Joint Research: 2 results,  Invited: 2 results)

  • [Int'l Joint Research] ロイヤルメルボルン工科大学(オーストラリア)

    • Related Report
      2019 Annual Research Report
  • [Int'l Joint Research] ミュンヘン工科大学(ドイツ)

    • Related Report
      2018 Annual Research Report
  • [Journal Article] Deuterium Labelling to Extract Local Stereochemical Information by VCD Spectroscopy in C-D Stretching Region: A Case Study of Sugars2022

    • Author(s)
      Mohamad Zarif Mohd Zubir, Nurul Fajry Maulida, Yoshihiro Abe, Yuta Nakamura, Mariam Abdelrasoul, Tohru Taniguchi, Kenji Monde
    • Journal Title

      Org. Biomol. Chem.

      Volume: 20 Issue: 5 Pages: 1067-1072

    • DOI

      10.1039/d1ob02317a

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Control of Reactions of Pyruvates by Catalysts: Direct Enantioselective Mannich Reactions of Pyruvates Catalyzed by Amine-based Catalyst Systems2022

    • Author(s)
      Santanu Mondal, Ravindra D. Aher, Venkati Bethi, Yu-Ju Lin, Tohru Taniguchi, Kenji Monde, Fujie Tanaka
    • Journal Title

      Org. Lett.

      Volume: 24 Issue: 9 Pages: 1853-1858

    • DOI

      10.1021/acs.orglett.2c00436

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Myrindole A, an Antimicrobial Bis-indole from a Marine Sponge Myrmekioderma sp.2021

    • Author(s)
      Moosmann Philipp、Taniguchi Tohru、Furihata Kazuo、Utsumi Hiroaki、Ise Yuji、Morii Yasuhiro、Yamawaki Nobuhiro、Takatani Tomohiro、Arakawa Osamu、Okada Shigeru、Matsunaga Shigeki
    • Journal Title

      Organic Letters

      Volume: 9 Issue: 9 Pages: 3477-3480

    • DOI

      10.1021/acs.orglett.1c00922

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Enantiodivergent One‐Pot Synthesis of Axially Chiral Biaryls Using Organocatalyst‐Mediated Enantioselective Domino Reaction and Central‐to‐Axial Chirality Conversion2021

    • Author(s)
      Koshino Seitaro、Taniguchi Tohru、Monde Kenji、Kwon Eunsang、Hayashi Yujiro
    • Journal Title

      Chemistry A European Journal

      Volume: 27 Issue: 63 Pages: 15786-15794

    • DOI

      10.1002/chem.202102797

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Bicyclo[2.2.2]octanes with a Quaternary Bridgehead Carbon by Diphenylprolinol Silyl Ether-mediated Domino Reaction2021

    • Author(s)
      Nariyoshi Umekubo, Tohru Taniguchi, Kenji Monde, Yujiro Hayashi
    • Journal Title

      Asian J. Org. Chem.

      Volume: 10 Issue: 12 Pages: 3261-3265

    • DOI

      10.1002/ajoc.202100573

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Exploration of Chromophores for VCD Couplet in Biomolecularly Transparent Infrared Region2021

    • Author(s)
      Tohru Taniguchi, Mohamad Zarif Mohd Zubir, Nobuyuki Harada, Kenji Monde
    • Journal Title

      Phys. Chem. Chem. Phys.

      Volume: 23 Issue: 48 Pages: 27525-27532

    • DOI

      10.1039/d1cp04074j

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] First enantioselective synthesis of salinipostin A, a marine cyclic enol-phosphotriester isolated from Salinispora sp.2019

    • Author(s)
      H. Okamura, T. Fujioka, N. Mori, T. Taniguchi, K. Monde, H. Watanabe, H. Takikawa
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Issue: 32 Pages: 150917-150917

    • DOI

      10.1016/j.tetlet.2019.07.008

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The Discovery of Fungal Polyene Macrolides via a Postgenomic Approach Reveals a Polyketide Macrocyclization by trans-Acting Thioesterase in Fungi2019

    • Author(s)
      Morishita Yohei、Zhang Huiping、Taniguchi Tohru、Mori Keiji、Asai Teigo
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 12 Pages: 4788-4792

    • DOI

      10.1021/acs.orglett.9b01674

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Post-genomic approach based discovery of alkylresorcinols from a cricket-associated fungus, Penicillium soppi2019

    • Author(s)
      Kaneko, A., Morishita, Y., Tsukada, K., Taniguchi, T., Asai, T.
    • Journal Title

      Org. Biomol. Chem.

      Volume: 17 Issue: 21 Pages: 5239-5243

    • DOI

      10.1039/c9ob00807a

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Use of plant hormones to activate silent polyketide biosynthetic pathways in Arthrinium sacchari, a fungus isolated from a spider2019

    • Author(s)
      Yohei Morishita, Yusuke Okazaki, Yi Yi Luo, Jun Nunoki, Tohru Taniguchi, Yoshiteru Oshima, Teigo Asai
    • Journal Title

      Org. Biomol. Chem.

      Volume: 17 Issue: 4 Pages: 780-784

    • DOI

      10.1039/c8ob02837k

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Determination of the Absolute Configurations and Sensory Properties of the Enantiomers of a Homologous Series (C6-C10) of 2-Mercapto-4-alkanones2019

    • Author(s)
      Kiske Christiane、Riegel Anja Devenie、Hopf Ronja、Kvindt Anna、Poplacean Iulia、Taniguchi Tohru、Swamy Mahadeva M. M.、Monde Kenji、Eisenreich Wolfgang、Engel Karl-Heinz
    • Journal Title

      Journal of Agricultural and Food Chemistry

      Volume: 67 Issue: 4 Pages: 1187-1196

    • DOI

      10.1021/acs.jafc.8b06599

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Preparation of Carbodiimides with One-Handed Axial Chirality2018

    • Author(s)
      Taniguchi Tohru、Suzuki Takahiro、Satoh Haruka、Shichibu Yukatsu、Konishi Katsuaki、Monde Kenji
    • Journal Title

      Journal of the American Chemical Society

      Volume: 140 Issue: 46 Pages: 15577-15581

    • DOI

      10.1021/jacs.8b08969

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Asymmetric C(sp3)-H Allylation of 2-Alkylpyridines2018

    • Author(s)
      Murakami Ryo、Sano Kentaro、Iwai Tomohiro、Taniguchi Tohru、Monde Kenji、Sawamura Masaya
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 57 Issue: 30 Pages: 9465-9469

    • DOI

      10.1002/anie.201802821

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Diels-Alder Reaction of α-Substituted and β,β-Disubstituted α,β-Enals via Diarylprolinol Silyl Ether for the Construction of All-Carbon Quaternary Stereocenters2016

    • Author(s)
      Y. Hayashi, B. P. Bondzic, T. Yamazaki, Y. Gupta, S. Ogasawara, T. Taniguchi, K. Monde
    • Journal Title

      Chem. Eur. J.

      Volume: 22 Issue: 44 Pages: 15874-15880

    • DOI

      10.1002/chem.201602345

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Presentation] VCD分光法による柔軟な酸化脂質の立体配置決定2022

    • Author(s)
      谷口透、井田南加、Davidson Agbo、門出健次
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Exploration of Biomolecularly Transparent IR Region for Structural Identification Using VCD2022

    • Author(s)
      Zarif Zubir, Nurul Fajry Maulida, Tohru Taniguchi, Kenji Monde
    • Organizer
      日本化学会第102春季年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Exploration of Biomolecularly Transparent IR Region for Structural Identification of Biomacromolecules Using VCD2021

    • Author(s)
      Mohamad Zarif Mohd Zubir, Nurul Fajry Maulida, Tohru Taniguchi, Kenji Monde
    • Organizer
      Symposium on Molecular Chirality 2021
    • Related Report
      2021 Annual Research Report
  • [Presentation] Three-dimensional structure of flexible lipids studied using VCD2021

    • Author(s)
      Tohru Taniguchi
    • Organizer
      Pacifichem 2021
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 不斉炭素を有する柔軟な脂肪酸とフッ素化誘導体のVCD構造研究2019

    • Author(s)
      ◯谷口 透・MAULIDA Nurul Fajry・門出 健次
    • Organizer
      Molecular Chirality 2019
    • Related Report
      2019 Annual Research Report
  • [Presentation] 不斉炭素を有する柔軟な脂肪酸とフッ素化誘導体のVCD(赤外円二色性)構造研究2019

    • Author(s)
      谷口 透・ファジュリ ヌルル・北原 卓弥・デェビィソン アグボ・門出 健次
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] VCD Studies on Three-Dimensional Structures of Flexible Molecules in Solution State2018

    • Author(s)
      Tohru Taniguchi
    • Organizer
      The 10th Singapore International Chemistry Conference
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited

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Published: 2018-04-23   Modified: 2023-01-30  

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