2003 Fiscal Year Final Research Report Summary
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
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
Chemical pharmacy
|
|---|
| Research Institution | Tokyo University of Pharmacy and Life Science |
|---|
Principal Investigator |
AOYAGI Yutaka Tokyo University of Pharmacy and Life Science, School of Pharmacy, Lecturer, 薬学部, 講師 (70212389)
|
|---|
| Project Period (FY) |
2002 – 2003
|
| Keywords | Lipase TL / GE3 / Hexadepsipeptides / Asymmetric Synthesis / Glycerols / Antitumor / Piperazic acid / SAR |
|---|
| 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.
|
