Chemoenzymatic Synthesis of Biologically Active Natural products via Lipase TL -Mediated Kinetic Resolution as a Key Step and their Structure Activity Relationship
| Project/Area Number |
14572014
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Tokyo University of Pharmacy and Life Science |
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Principal Investigator |
AOYAGI Yutaka Tokyo University of Pharmacy and Life Science, School of Pharmacy, Lecturer, 薬学部, 講師 (70212389)
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| Project Period (FY) |
2002 – 2003
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| Project Status |
Completed (Fiscal Year 2003)
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| Budget Amount *help |
¥1,600,000 (Direct Cost: ¥1,600,000)
Fiscal Year 2003: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 2002: ¥1,100,000 (Direct Cost: ¥1,100,000)
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| Keywords | Lipase TL / GE3 / Hexadepsipeptides / Asymmetric Synthesis / Glycerols / Antitumor / Piperazic acid / SAR / 光学分割 / ジテルペン / 2級アルコール / 速度論的光学分割 / グリセロール / 光学活性ピペラジン酸 / 低温活性酵素 |
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| Research Abstract |
1)Lipase TL-mediated kinetic resolution of 2-pentanol (C5 unit) and 2-propanol (C3 unit) proceeded in the presence of base at low temperature to give the corresponding optically pure alcohols and acetates in good yields, respectively. The 2-pentanol and its acetate thus obtained were converted both enantiomers of piperazic acid derivatives, which are important segments of hexadepsipeptide GE3. 2)Cytotoxic ent-kaurene diterpenes were isolated from Rabdosia excisa to obtained substrates for Lipase TL-mediated regioselective acetylation of polyhydroxy natural products. 3)Efficient transformation of 7,14-dihydroxy-ent-kaurenes to tetracyclic ent-abietanes under Mitsunobu reaction conditions were developed. The tetracyclyc ent-abietanes have been found to be potent cytotoxic agents. 4)SAR study on ent-kaurenes and tetracyclic ent-abietanes were also examined.
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Report
(3 results)
Research Products
(9 results)
