Elucidation of Phytocrome Functions Based on Syntheses of Sterically Locked Phytochrome Chromophores

2015 Fiscal Year Final Research Report

• Project/Area Number: 25620028
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Kanazawa University
• Principal Investigator: Ukaji Yutaka 金沢大学, 物質化学系, 教授 (80193853)
• Co-Investigator(Renkei-kenkyūsha): SOETA TAKAHIRO 金沢大学, 物質化学系, 准教授 (10506819)
• Project Period (FY): 2013-04-01 – 2016-03-31
• Keywords: フィトクロム / 生体分子 / 植物機能 / 光スイッチ / 立体固定型 / 酸化的官能基化 / テトラピロール発色団

Outline of Final Research Achievements

Phytochromes play critical roles in various light-regulated processes through photoconversion from Pr to Pfr is thought to be a Z-to-E isomerization around the C15-C16 double bond. To elucidate the functions of phytochromes, the sterically locked tetrapyrrole chromophores were synthesized especially via oxidative functionalization of pyrrole compounds. Oxidation of the C-ring moiety with DDQ afforded the corresponding aldehyde, which was applied to the synthesis of the sterically locked seven-membered and 8-membered 15E-anti CD-ring component. Oxidation of the CD-ring component with NBS at the meso-position was achieved to give the corresponding meso-bromo CD-ring compounds. The introduction of carbon skeleton was realized by treatment with Grignard reagents. Finally, the substrate with leaving group at omega-position was converted to a meso-anchored sterically fixed 15E-chromophore.

Free Research Field

有機合成化学