Biomimetic iterative method for polyketide synthesis

2019 Fiscal Year Final Research Report

• Project/Area Number: 17K05854
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: The University of Tokyo
• Principal Investigator: Akagawa Kengo 東京大学, 生産技術研究所, 助教 (60548733)
• Project Period (FY): 2017-04-01 – 2020-03-31
• Keywords: ポリケチド / 繰り返し合成 / 固相合成 / マロン酸ハーフチオエステル / 含フッ素ポリケチド

Outline of Final Research Achievements

Polyketides constitute a class of compounds with a wide variety of structures and oxidation states. Despite the diversity of polyketide molecules, they are synthesized via the common iterative process in nature. By mimicking the biological system, we established the iterative synthetic method for affording various types of polyketides. Chain elongation of a carboxylic acid with malonic acid half thioester was used as the key reaction for the iterative synthesis. It was shown that different types of polyketides could be synthesized by repeating a few kinds of reactions. The iterative method was extended to the solid-phase synthesis for obtaining polyketides with simple operations.

Free Research Field

有機合成化学

Academic Significance and Societal Importance of the Research Achievements

ポリケチドは医薬品開発の基礎となる重要な化合物群であり、本研究では繰り返し反応によるポリケチド合成が可能な手法を開発した。異なる種類の天然ポリケチドを統一的な手段で合成できることに加え、フッ素や窒素原子を任意の位置に導入した非天然型のポリケチド合成も可能である。簡便な操作の繰り返しで多種類のポリケチド化合物が得られるため、本法を利用した新たな医薬品の創製が期待できる。