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Development of flavopeptide catalysts for enzyme-like asymmetric aerobic oxygenations

Research Project

Project/Area Number 18K05108
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionThe University of Tokushima

Principal Investigator

ARAKAWA Yukihiro  徳島大学, 大学院社会産業理工学研究部(理工学域), 助教 (70709203)

Co-Investigator(Kenkyū-buntansha) 今田 泰嗣  徳島大学, 大学院社会産業理工学研究部(理工学域), 教授 (60183191)
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: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2019: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2018: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsフラビン / ペプチド / 酸化反応 / 不斉触媒反応 / 酸素添加反応 / 不斉触媒
Outline of Final Research Achievements

This study has been carried out for the purpose of developing flavopeptides that catalyze flavoenzyme-like aerobic oxygenations in a highly enantioselective manner. Although the asymmetric induction has not been achieved, we have obtained some important results that will guide the development of chiral flavopeptide catalysts in the future, which include 1) flavopeptide-catalyzed aerobic oxygenations in a homogeneous system, 2) enzyme-like regiodivergent behavior of a flavopeptide catalyst in aerobic Baeyer-Villiger reaction, 3) effect of stereochemistry on the catalytic activity of flavopeptides, and 4) photoinduced alfa-oxyamination of aldehydes using flavopeptides as a photoredox catalyst.

Academic Significance and Societal Importance of the Research Achievements

本研究の成果は、今後、酸素添加反応に限らず、光レドックス触媒反応を含む幅広い反応系において、フラボペプチドによる高度なエナンチオ制御を実現するための指針となるものであり、それらは従来の重金属塩酸化剤の使用に依存しない安全で環境にやさしい理想的な酸化的分子変換技術の発展、延いては持続可能な開発目標(SDGs)に貢献する重要な課題である。

Report

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

    (24 results)

All 2021 2020 2019 2018

All Journal Article (8 results) (of which Peer Reviewed: 8 results,  Open Access: 8 results) Presentation (16 results) (of which Int'l Joint Research: 7 results,  Invited: 2 results)

  • [Journal Article] Effect of stereochemistry on the catalytic activity of flavopeptides2021

    • Author(s)
      Yukihiro Arakawa, Nao Takechi, Ken Yamanomoto, Keiji Minagawa, Yasushi Imada
    • Journal Title

      Tetrahedron Letters

      Volume: 61 Pages: 153107-153107

    • DOI

      10.1016/j.tetlet.2021.153107

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Alloxazinium-Resins as Readily Available and Reusable Oxidation Catalysts2021

    • Author(s)
      Yukihiro Arakawa, Takayuki Kawahara, Keiji Minagawa, Yasushi Imada
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: - Issue: 6 Pages: 1728-1730

    • DOI

      10.1246/bcsj.20210096

    • NAID

      130008066556

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] An uncommon use of irradiated flavins: Br?nsted acid catalysis2020

    • Author(s)
      Yukihiro Arakawa, Tomohiro Mihara, Hiroki Fujii, Keiji Minagawa, Yasushi Imada
    • Journal Title

      Chemical Communications

      Volume: 56 Issue: 42 Pages: 5661-5664

    • DOI

      10.1039/d0cc01960g

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Nucleophilic Addition to Nitrones Using a Flow Microreactor2020

    • Author(s)
      Yukihiro Arakawa, Shun Ueta, Takuma Okamoto, Keiji Minagawa, Yasushi Imada
    • Journal Title

      Synlett

      Volume: 31 Issue: 09 Pages: 866-870

    • DOI

      10.1055/s-0039-1691601

    • NAID

      120006959768

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Preparation of flavin-containing mesoporous network polymers and their catalysis2020

    • Author(s)
      Yukihiro Arakawa、Fumiaki Sato、Kenta Ariki、Keiji Minagawa、Yasushi Imada
    • Journal Title

      Tetrahedron Letters

      Volume: 61 Issue: 14 Pages: 151710-151710

    • DOI

      10.1016/j.tetlet.2020.151710

    • NAID

      120007188797

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Efficient Use of Photons in Photoredox/Enamine Dual Catalysis with a Peptide-Bridged Flavin-Amine Hybrid2019

    • Author(s)
      Takuma Tagami、Yukihiro Arakawa、Keiji Minagawa、Yasushi Imada
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 17 Pages: 6978-6982

    • DOI

      10.1021/acs.orglett.9b02567

    • NAID

      120006877715

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Enzyme-like Regiodivergent Behavior of a Flavopeptide Catalyst in Aerobic Baeyer-Villiger Oxidation2018

    • Author(s)
      Ken Yamanomoto, Hazuki Kita, Yukihiro Arakawa, Keiji Minagawa, Yasushi Imada
    • Journal Title

      CHIMIA

      Volume: 72 Issue: 12 Pages: 866-869

    • DOI

      10.2533/chimia.2018.866

    • NAID

      120006771697

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Advanced Flavin Catalysts Elaborated with Polymers2018

    • Author(s)
      Yukihiro Arakawa, Keiji Minagawa, Yasushi Imada
    • Journal Title

      Polymer Journal

      Volume: 50 Issue: 10 Pages: 941-949

    • DOI

      10.1038/s41428-018-0089-8

    • NAID

      120006576963

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] Photoinduced Asymmetric α-Oxyamination of Aldehydes Using a Flavin Catalyst and Blue LED Irradiation2021

    • Author(s)
      Kazuaki Nishitani, Yukihiro Arakawa, Keiji Minagawa, Yasushi Imada
    • Organizer
      the LED General Forum 2021
    • Related Report
      2020 Annual Research Report
  • [Presentation] Nucleophilic Addition of Vinyl Ethers to a Flavinium Salt2020

    • Author(s)
      Naoki Hasegawa, Yukihiro Arakawa, Keiji Minagawa, Yasushi Imada
    • Organizer
      6th International Forum on Advanced Technologies
    • Related Report
      2020 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 空気酸化―樹脂担持法による新規フラビニウム塩の合成2020

    • Author(s)
      坂東新之助,荒川幸弘,南川慶二,今田泰嗣
    • Organizer
      第35回中国四国地区高分子若手研究会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 1,2-ビス(アルキルアミド)シクロヘキサンのゲル化を利用した含フラビン物理ゲルの物性評価2020

    • Author(s)
      三好正敏,荒川幸弘,南川慶二,今田泰嗣
    • Organizer
      35回中国四国地区高分子若手研究会
    • Related Report
      2020 Annual Research Report
  • [Presentation] Flavin-Peptide-Polymer Hybrid as a Biomimetic Oxidation Catalyst2019

    • Author(s)
      Yukihiro Arakawa
    • Organizer
      International Congress on Pure & Applied Chemistry (ICPAC) Yangon 2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Flavin-Peptide-Polymer Hybrid as a Biomimetic Oxidation Catalyst2019

    • Author(s)
      Yukihiro Arakawa, Keiji Minagawa, Yasushi Imada
    • Organizer
      The 1st International Symposium on Hybrid Catalysis for Enabling Molecular Synthesis on Demand
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Flavohybrids That Enable Efficient Use of Biomimetic Catalytic Species2019

    • Author(s)
      荒川幸弘, 南川慶二, 今田泰嗣
    • Organizer
      第12回有機触媒シンポジウム
    • Related Report
      2019 Research-status Report
  • [Presentation] フラボペプチド触媒における立体化学の触媒活性への影響2019

    • Author(s)
      武知奈穂, 荒川幸弘, 南川慶二, 今田泰嗣
    • Organizer
      2019年日本化学会中国四国支部大会徳島大会
    • Related Report
      2019 Research-status Report
  • [Presentation] 樹脂担持フラボペプチド触媒における立体化学の触媒活性への影響2019

    • Author(s)
      武知奈穂, 荒川幸弘, 南川慶二, 今田泰嗣
    • Organizer
      第34回中国四国地区高分子若手研究会
    • Related Report
      2019 Research-status Report
  • [Presentation] Efficient Use of Photons in Photoredox/Enamine Dual Catalysis with a Flavin-Amine Hybrid2019

    • Author(s)
      Takuma Tagami, Yukihiro Arakawa, Keiji Minagawa, Yasushi Imada
    • Organizer
      5th International Symposium on Middle Molecular Strategy (ISMMS-5)
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] 均一系フラボペプチド触媒による酵素類似酸素酸化反応2019

    • Author(s)
      上田祐, 喜多葉月, 山野本健, 荒川幸弘, 南川慶二, 今田泰嗣
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] N5-Unmodified flavins that catalyze enzyme-like oxidations2019

    • Author(s)
      山野本健, 喜多葉月, 荒川幸弘, 南川慶二, 今田泰嗣
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Presentation] Design of Peptide-Containing N5-Unmodified Neutral Flavins That Catalyze Aerobic Oxygenations2018

    • Author(s)
      Ken Yamanomoto, Hazuki Kita, Yukihiro Arakawa, Keiji Minagawa, Yasushi Imada
    • Organizer
      The 12th SPSJ International Polymer Conference
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Neutral Flavin-Catalyzed Oxidations with Hydrogen Peroxide2018

    • Author(s)
      Ken Yamanomoto, Hazuki Kita, Yukihiro Arakawa, Keiji Minagawa, Yasushi Imada
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Development of Aerobic Oxygenation Catalyzed by N5-Unmodified Neutral Flavins2018

    • Author(s)
      Hazuki Kita, Ken Yamanomoto, Yukihiro Arakawa, Keiji Minagawa, Yasushi Imada
    • Organizer
      The 14th International Kyoto Conference on New Aspects of Organic Chemistry
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research
  • [Presentation] Resin-Supported Flavopeptides That Catalyze Aerobic Oxygenations2018

    • Author(s)
      荒川幸弘
    • Organizer
      第67回高分子学会年次大会
    • Related Report
      2018 Research-status Report
    • Invited

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

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