Efficient organic synthesis utilizing microbial enzyme catalysts

2016 Fiscal Year Final Research Report

• Project/Area Number: 26450143
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Bioorganic chemistry
• 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): 2014-04-01 – 2017-03-31
• Keywords: 立体選択的反応 / 位置選択的反応 / リパーゼ触媒 / ポリフェノール / 複素環化合物

Outline of Final Research Achievements

Complementary and synergistic utilization of enzyme-catalyzed reactions and chemical transformation was studied, toward the efficient synthesis of complex target molecules involving valuable natural and unnatural products. The achievements are shown below. Lipase-catalyzed transesterification proceeded with specific site-selectivity contrasting to chemical transformations, and the syntheses of selinone and astringin, artepillin C became successful. It was revealed that the transesterification under non-aqueous conditions was advantageous for the substrates which are labile to water and/or prone to protonation under aqueous conditions. The preparation of highly enantiomerically pure (R)-3-hydroxy-N-methylpiperidine by the lipase-catalyzed kinetic resolution of corresponding racemate was established. The synthesis of enantiomers of NMB carboxylic acid was also successful, by discriminating he stereochemistry of remote chiral center in a primary acetate, as the key step.

Free Research Field

有機合成化学、生物有機化学