Synthesis of Optically Active Flower-inducing Fatty Acids, KODA Analogs

• Project/Area Number: 22580114
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Bioproduction chemistry/Bioorganic chemistry
• Research Institution: Ibaraki University
• Principal Investigator: TOSHIMA Hiroaki 茨城大学, 農学部, 教授 (50237088)
• Project Period (FY): 2010 – 2012
• Project Status: Completed (Fiscal Year 2012)
• Budget Amount: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000); Fiscal Year 2012: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000); Fiscal Year 2011: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000); Fiscal Year 2010: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
• Keywords: KODA / 脂肪酸 / シクロプロパン / 花芽誘導活性 / 植物ホルモン様活性 / 化学合成 / 光学活性類縁体 / ＫＯＤＡ / 植物生理活性 / 光学活性体 / 類縁体

Research Abstract

Stereoselective synthesis of promising flower-inducing fatty acids, KODA analogs, was designed to obtain the desired stereoisomer viacoupling between chiral sulfone and aldehyde segments. Coupling of the both segments and subsequent assembly gave the desired analog. This strategy made it possible to synthesize the remaining stereoisomeric analogs. By using synthetic KODA analogs, the study of mechanistic elucidation of flower-inducing activity by KODA and the development of flower-inducing regulator are expected to progress.

Research Products

• [Journal Article] Stereoselective Synthesis of a Promising Flower-Inducing KODA Analog, (9R,12S,13R,15Z)-9-Hydroxy-12,13-methylene-10-oxooctadec-15-enoic Acid (2013)
  • Author(s): Shin SHIMOMURA, Shuho OYAMA, Kyohei NAKANO, Morifumi HASEGAWA, and Hiroaki TOSHIMA
  • Journal Title: Biosci. Biotechnol. Biochem. Volume: 77(6)in press
  • NAID: 10031184713
  • URL: http://dx.doi.org/10.1271/bbb.130243
  • Peer Reviewed
• [Journal Article] Stereoselective Synthesis of a Promising Flower-inducing KODA Analog, (9R,12S,13R,15Z)-9-Hydroxy-12,13-methylene-10-oxooctadec-15-enoic Acid (2013)
  • Author(s): Shin Simomura
  • Journal Title: Biosci. Biotechnol. Biocem. Volume: 77
  • Peer Reviewed
• [Presentation] 抗β-酸化型CP-KODA(30x0-CP-KODA) の合成研究 (2013)
  • Author(s): 大山秀芳、中山ともみ、長谷川守文、戸嶋浩明
  • Organizer: 日本農芸化学会2013年度大会
  • Place of Presentation: 東北大学
  • Year and Date: 2013-03-26
• [Presentation] シクロプロパン環導入型KODA 類縁体の立体異性体選択的合成 (2011)
  • Author(s): 下村伸、長谷川守文、横山峰幸、伊福欧二、山村庄亮、戸嶋浩明
  • Organizer: 日本農芸化学会2011 年度大会
  • Place of Presentation: 京都女子大学
  • Year and Date: 2011-03-26
• [Presentation] シクロプロパン環導入型KODA類縁体の立体異性体選択的合成 (2011)
  • Author(s): 下村伸
  • Organizer: 日本農芸化学会2011年度大会(2011)
  • Place of Presentation: 京都女子大学
  • Year and Date: 2011-03-26
• [Presentation] シクロプロパン環導入型KODA 類縁体の立体異性体選択的合成法に関する研究 (2010)
  • Author(s): 下村伸、長谷川守文、横山峰幸、伊福欧二、山村庄亮、戸嶋浩明
  • Organizer: 日本化学会 第4回関東支部大会
  • Place of Presentation: 筑波大学
  • Year and Date: 2010-08-30
• [Presentation] シクロプロパン環導入型KODA類縁体の立体異性体選択的合成法に関する研究 (2010)
  • Author(s): 下村伸
  • Organizer: 日本化学会第4回関東支部大会(2010)
  • Place of Presentation: つくば大学
  • Year and Date: 2010-08-30
• [Presentation] 抗β―酸化型CP-KODA(30x0-CP-KODA)の合成研究
  • Author(s): 大山秀芳
  • Organizer: 日本農芸化学会２０１３年度大会
  • Place of Presentation: 東北大学（仙台）