Development of flavopeptide catalysts for enzyme-like asymmetric aerobic oxygenations

2020 Fiscal Year Final Research Report

• Project/Area Number: 18K05108
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 33020:Synthetic organic chemistry-related
• Research Institution: The University of Tokushima
• Principal Investigator: ARAKAWA Yukihiro 徳島大学, 大学院社会産業理工学研究部(理工学域), 助教 (70709203)
• Co-Investigator(Kenkyū-buntansha): 今田 泰嗣 徳島大学, 大学院社会産業理工学研究部(理工学域), 教授 (60183191)
• Project Period (FY): 2018-04-01 – 2021-03-31
• Keywords: フラビン / ペプチド / 酸化反応 / 不斉触媒反応

Outline of Final Research Achievements

This study has been carried out for the purpose of developing flavopeptides that catalyze flavoenzyme-like aerobic oxygenations in a highly enantioselective manner. Although the asymmetric induction has not been achieved, we have obtained some important results that will guide the development of chiral flavopeptide catalysts in the future, which include 1) flavopeptide-catalyzed aerobic oxygenations in a homogeneous system, 2) enzyme-like regiodivergent behavior of a flavopeptide catalyst in aerobic Baeyer-Villiger reaction, 3) effect of stereochemistry on the catalytic activity of flavopeptides, and 4) photoinduced alfa-oxyamination of aldehydes using flavopeptides as a photoredox catalyst.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

本研究の成果は、今後、酸素添加反応に限らず、光レドックス触媒反応を含む幅広い反応系において、フラボペプチドによる高度なエナンチオ制御を実現するための指針となるものであり、それらは従来の重金属塩酸化剤の使用に依存しない安全で環境にやさしい理想的な酸化的分子変換技術の発展、延いては持続可能な開発目標（SDGs）に貢献する重要な課題である。