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

• Project/Area Number: 15K16551
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Multi-year Fund
• Research Field: Biomolecular chemistry
• Research Institution: Hokkaido 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: ¥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.

Research Products

• [Journal Article] Total synthesis and biological activity of dolastatin 16 (2017)
  • 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
  • Peer Reviewed
• [Presentation] Total Synthesis of Antifouling Natural Products toward Development of Molecular Probe (2016)
  • 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
  • Int'l Joint Research / Invited
• [Presentation] Total Synthesis of Antifouling Natural Products toward Development of Molecular Probe (2016)
  • 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
  • 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
  • Invited
• [Presentation] Synthetic Study on Dolastatin 16 (2016)
  • 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
• [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）
• [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）
• [Presentation] total synthesis and structure-activity relationship of omaezallene toward the development of molecular probe for antifouling substance (2015)
  • 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
  • Int'l Joint Research
• [Presentation] Synthetic Study on Dolastatin 16 (2015)
  • 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
• [Presentation] Synthetic Study on Dolastatin 16 (2015)
  • 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