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2018 Fiscal Year Final Research Report

Studies toward the total synthesis of Caribbean ciguatoxin for the development of a highly sensitive antibody-based immunoassy

Research Project

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Project/Area Number 16H03278
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Biomolecular chemistry
Research InstitutionTohoku University

Principal Investigator

Sasaki Makoto  東北大学, 生命科学研究科, 教授 (80235267)

Research Collaborator Iwasaki Kotaro  
Fujii Ikuo  
Tsumuraya Takeshi  
Project Period (FY) 2016-04-01 – 2019-03-31
Keywordsカリビアンシガトキシン / シガテラ中毒 / 効率的全合成 / 抗体作製 / 高感度微量検出法
Outline of Final Research Achievements

Ciguatera is a naturally occurring seafood poisoning prevalent in tropical and subtropical regions of the Pacific Ocean, Indian Ocean, and Caribbean Sea with more than 20,000-60,000 victims and continues to be a serious worldwide public health concern. Caribbean ciguatoxins, the principal causative toxins for ciguatera around the Caribbean Sea areas, possess the most complicated structure among the ciguatoxins known to date. An efficient synthesis route to the LMN-ring fragment of Caribbean ciguatoxin C-CTX-1 has been developed. The key feature of the synthesis includes hydrogen atom transfer based reductive olefin cross-coupling to access a sterically congested tetrasubstituted stereogenic center on the strained seven-membered M-ring with the pseudoaxially oriented 1,3-dimethyl structure. Further studies towards the synthesis of the right-hand HIJKLMN-ring fragment through convergent union of the HI- and KLMN-ring fragments based on Suzuki-Miyaura reaction are underway.

Free Research Field

天然物合成化学、有機化学

Academic Significance and Societal Importance of the Research Achievements

近年、カリビアンシガトキシンによるシガテラ食中毒が世界的に拡大しつつあり、その予防対策は急務の課題となっている。カリビアンシガトキシンは天然から極微量しか得られないため、毒判定のための純粋な標準サンプルの供給や微量検出法の開発のために、化学合成による物質供給が世界的に強く望まれている。本研究により、カリビアンシガトキシン合成における最難関課題の一つであるLMN環部の合成法が確立できた。これにより、分子右半分に相当するHIJKLMN環フラグメントの合成とそれを用いたモノクローナル抗体の作製への道が拓かれた。今後、カリビアンシガトキシンの微量検出法の開発に貢献する重要な成果である。

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Published: 2020-03-30   Modified: 2022-01-27  

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