Efficient organic synthesis utilizing microbial enzyme catalysts
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
|
Project Status |
Completed (Fiscal Year 2016)
|
Budget Amount *help |
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2015: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2014: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
|
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 / リパーゼ / 含窒素複素環 / 速度論的分割 / 脱アセチル化 / エステル交換 / 遠隔位不斉中心 |
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.
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Report
(4 results)
Research Products
(13 results)