1999 Fiscal Year Final Research Report Summary
Preparation of Anti-Ciguatoxin Antibody and Synthetic Study of Ciguatoxin Science
| Project/Area Number |
09640621
|
|---|
| Research Category |
Grant-in-Aid for Scientific Research (C)
|
| Allocation Type | Single-year Grants |
|---|
| Section | 一般 |
|---|
| Research Field |
Organic chemistry
|
|---|
| Research Institution | TOHOKU UNIVERSITY |
|---|
Principal Investigator |
OISHI Toru Chemistry, Tohoku Univ., Lecturer, 大学院・理学研究科, 講師 (90241520)
|
|---|
| Project Period (FY) |
1997 – 1999
|
| Keywords | ciguatoxin / polycyclicether / seafood poisoning / anti-ciguatoxin antibody / total synthesis / convergent synthesis / olefin metathesis |
|---|
| Research Abstract |
Ciguatera is a widespread human food poisoning that is caused by fishes dwelling in coral reefs in the tropics and subtropics. Over twenty thousands people in subtropical and tropical regions suffered annually from ciguatera caused by poisonous fishes dwelling in coral reefs. Ciguatoxin is the principal toxin of ciguatera, and we determined the absolute configuration by CD exciton chirality method. Considerable attention has been paid to develop an analyzing method for detecting the toxic fishes, because the prevalence of ciguatera has threatened public health in tropical regions. Therefore, anti-ciguatoxin antibody is needed for this purpose. We succeeded in the preparation of anti-ciguatoxin antibody using AB-ring protein conjugates as haptens. Synthesis of ciguatoxin has received considerable attention among synthetic chemists due to the striking feature and biological features of these toxins. We developed a new method useful for constructing polycyclic ether systems using alkylation and ring-closing metathesis reaction. Based on this strategy, we successfully synthesized the ABCED ring fragment starting with the AB and E ring, respectively. Alternatively, we synthesized the IJKLM ring fragment via Tebbe reagent mediated ring-closing metathesis, and the chemo- and stereoselective reduction of the methyl acetal. Studies toward total synthesis of ciguatoxin are currently underway.
|
