Synthetic studies and chemical biology of biologicaly active natural tetramic acids

• Project/Area Number: 15K07418
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Bioorganic chemistry
• Research Institution: Tokyo University of Agriculture
• Principal Investigator: Yajima Arata 東京農業大学, 生命科学部, 准教授 (30328546)
• Research Collaborator: Ohki Chiaki
• Project Period (FY): 2015-04-01 – 2018-03-31
• Project Status: Completed (Fiscal Year 2017)
• Budget Amount: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000); Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
• Keywords: 天然物化学 / 有機合成化学 / 薬剤耐性 / 天然有機化合物 / 全合成

Outline of Final Research Achievements

Synthesis of Signermycin B with histidine kinase WalK inhibitory activity was investigated. We could design the substrate for intramolecular Diels-Alder reaction and investigate the construction of the decaline ring system.
Next, we synthesized ancolinoside A aglycone having type 1 Mattrix proteinase inhibitory activity. On the basis of the comparison of synthetic products and natural products, we were able to determine the absolute configuration of natural products.
Regarding the synthesis of ilicicolins, ring formation by oxidative reaction conditions was examined for the pyridone ring-forming reaction.

Research Products

• [Journal Article] Nitro-Mannich reaction and intramolecular 1,3-dipolar cycloaddition route to acylpyrrolidinones: Synthesis of a tetramic acid and (+)-laccarin (2018)
  • Author(s): Katsuta Ryo、Ichijo Hiroki、Oouchi Ginka、Yajima Arata、Ishigami Ken、Nukada Tomoo
  • Journal Title: Tetrahedron Letters Volume: 59 Issue: 24 Pages: 2352-2355
  • DOI: 10.1016/j.tetlet.2018.05.014
  • Peer Reviewed
• [Presentation] Ancorinoside類の合成研究 (2017)
  • Author(s): 大木千明, 矢島新, 勝田亮, 額田恭郎
  • Organizer: 日本農芸化学会2017年度大会
• [Presentation] Ancorinoside類の合成研究 (2017)
  • Author(s): 大木千明, 矢島新, 勝田亮, 額田恭郎
  • Organizer: 日本農芸化学会2017年度支部大会
  • Place of Presentation: 京都女子大学(京都府京都市)
• [Presentation] Ancorinoside類の合成研究 (2016)
  • Author(s): 大木千明, 矢島新, 勝田亮, 額田恭郎
  • Organizer: 日本農芸化学会関東支部2016年度支部大会
  • Place of Presentation: 日本獣医生命科学大学(東京都武蔵野市)
• [Presentation] Synthetic studies of biologically active mannosylated 3-acyltetramic acids (2015)
  • Author(s): Arata Yajima, Chieko Ida, Akihiro Kawajiri, Ryo Katsuta, Tomoo Nukada
  • Organizer: 2015 International Chemical Congress of Pacific Basin Societies (PACIFICHEM)
  • Place of Presentation: Waikiki
  • Year and Date: 2015-12-18
  • Int'l Joint Research
• [Presentation] Synthetic studies of epicoccamides and virgineone, biologically active mannosylated 3-acyltetramic acids (2015)
  • Author(s): Arata Yajima, Chieko Ida, Akihiro Kawajiri, Ryo Katsuta, Tomoo Nukada
  • Organizer: The 13th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-13)
  • Place of Presentation: Kyoto
  • Year and Date: 2015-11-11
  • Int'l Joint Research