Synthetic Studies of Bioactive Substances Based on Site- and Stereoselective Reactions

2021 Fiscal Year Final Research Report

• Project/Area Number: 19K05849
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 38040:Bioorganic chemistry-related
• Research Institution: Keio University
• Principal Investigator: Sugai Takeshi 慶應義塾大学, 薬学部(芝共立), 教授 (60171120)
• Project Period (FY): 2019-04-01 – 2022-03-31
• Keywords: 位置選択的反応 / リパーゼ / 脱アセチル化 / 高圧蒸気滅菌器 / 加水分解 / ポリオール / 半合成 / 天然配糖体

Outline of Final Research Achievements

In the organic process chemistries, the integrated use of chemo- (organic synthesis) enzymatic (biotechnology) transformation approach as well as the utilization of naturally occurring starting materials takes advantages over individual procedures, towards the best solution to make the design and diagram for target compounds. Catalytic activities of cheaply commercially available lipases in transesterification in organic solvents were demonstrated for deprotection of phenolic esters and esterification of aliphatic alcohols. I achieved the syntheses of catatherasmols and tournefolin B, based on the site-selectivity which was clarified through this study. In contrast, the complementary use of chemical site-selectivity on transformation of aromatic substances enabled the new efficient syntheses of polymethoxybenzenes. Finally, partial hydrolysis of naturally occurring C-glycoside flavone in high-pressure steam sterilizer provided an efficient route to chafuroside B.

Free Research Field

有機化学、生物有機化学、生物資源科学

Academic Significance and Societal Importance of the Research Achievements

3年間の研究を通じ、天然資源や酵素触媒がうまく使えるようになったため、生物活性物質の生物作用解明や前臨床・臨床試験への提供などが実現する可能性が増大した。また、多くの研究者に再現・活用してもらえる機会も増え、さらなる発展や波及効果が期待される。