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Synthetic study on fluorecent probe of antifouling natural products toward elucidation of molecular mechanism

Research Project

Project/Area Number 15K16551
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Biomolecular chemistry
Research InstitutionHokkaido University

Principal Investigator

Umezawa Taiki  北海道大学, 地球環境科学研究院, 准教授 (20503618)

Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2016: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2015: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords天然有機化合物 / 付着阻害 / 全合成
Outline of Final Research Achievements

This study aims syntheses of fluorescent probe of antifouling natural products. As lead compounds for antifouling materials, omaezallene (brominated compound) and dolastatin 16 (cyclic peptide) are selected becuase these exhibit strong antifouling activity along with very low toxicity toward cypris larvae of Amphibalanus amphitrite. Elucidation of molecular mechanism of antifouling activity expects the development of ideal antifouling material.
Syntheses of omaezallene derivatives was achieved, which includes fluorescent derivative. A new synthetic pathway to dolastatin 16 and the antifouling activity of synthetic sample were revealed. Functionalization method toward fluorescent compound was also developed.

Report

(3 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • Research Products

    (10 results)

All 2017 2016 2015

All Journal Article (1 results) (of which Peer Reviewed: 1 results) Presentation (9 results) (of which Int'l Joint Research: 3 results,  Invited: 3 results)

  • [Journal Article] Total synthesis and biological activity of dolastatin 162017

    • Author(s)
      1.Casalme, L. O., Yamauchi, A., Sato, A., Petitbois, J. G., Nogata, Y., Yoshimura, E., Okino, T., Umezawa, T., & Matsuda, F.
    • Journal Title

      Org. Biomol. Chem.

      Volume: 15 Issue: 5 Pages: 1140-1150

    • DOI

      10.1039/c6ob02657e

    • NAID

      120006374983

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Presentation] Total Synthesis of Antifouling Natural Products toward Development of Molecular Probe2016

    • Author(s)
      Taiki Umezawa
    • Organizer
      International Conference on Chemistry, Chemical Process and Engineering 
    • Place of Presentation
      ジョグジャカルタ(インドネシア)
    • Year and Date
      2016-11-15
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Total Synthesis of Antifouling Natural Products toward Development of Molecular Probe2016

    • Author(s)
      Taiki Umezawa
    • Organizer
      the International Conference on Biodiversity and Chemical Biology of Marine and Terrestrial Life in the Philippine Region
    • Place of Presentation
      ボホール(フィリピン)
    • Year and Date
      2016-10-16
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] プローブ合成を指向した着生阻害天然物の全合成2016

    • Author(s)
      梅澤大樹
    • Organizer
      第11回化学生態学研究会
    • Place of Presentation
      湯の川プリンスホテル渚亭(北海道、函館市)
    • Year and Date
      2016-07-01
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Synthetic Study on Dolastatin 162016

    • Author(s)
      Loida Casalme、梅澤大樹、松田冬彦
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス(京田辺市)
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] オマエザレン誘導体の合成研究2016

    • Author(s)
      甘中美帆、梅澤大樹、松田冬彦
    • Organizer
      北海道支部2016年夏季研究発表会
    • Place of Presentation
      室蘭工業大学(北海道、室蘭市)
    • Related Report
      2016 Annual Research Report
  • [Presentation] Dolastatin 16誘導体の合成研究2016

    • Author(s)
      山内有紗、梅澤大樹、松田冬彦
    • Organizer
      北海道支部2016年夏季研究発表会
    • Place of Presentation
      室蘭工業大学(北海道、室蘭市)
    • Related Report
      2016 Annual Research Report
  • [Presentation] total synthesis and structure-activity relationship of omaezallene toward the development of molecular probe for antifouling substance2015

    • Author(s)
      梅澤大樹、吉村えり奈、野方靖行、沖野龍文、松田冬彦
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015
    • Place of Presentation
      ホノルル(アメリカ)
    • Year and Date
      2015-12-16
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthetic Study on Dolastatin 162015

    • Author(s)
      Loida Casalme、佐藤彰則、飴田康人、梅澤大樹、松田冬彦
    • Organizer
      第57回天然有機化合物討論会
    • Place of Presentation
      神奈川県民ホール(横浜市)
    • Year and Date
      2015-09-09
    • Related Report
      2015 Research-status Report
  • [Presentation] Synthetic Study on Dolastatin 162015

    • Author(s)
      Loida Casalme、佐藤彰則、飴田康人、梅澤大樹、松田冬彦
    • Organizer
      北海道支部2015年夏季研究発表会
    • Place of Presentation
      北海道教育大学函館校(函館市)
    • Year and Date
      2015-07-18
    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2018-03-22  

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