Studies toward the total synthesis of Caribbean ciguatoxin for the development of a highly sensitive antibody-based immunoassy
| Project/Area Number |
16H03278
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Biomolecular chemistry
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| Research Institution | Tohoku University |
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Principal Investigator |
Sasaki Makoto 東北大学, 生命科学研究科, 教授 (80235267)
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| Research Collaborator |
Iwasaki Kotaro
Fujii Ikuo
Tsumuraya Takeshi
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| Project Period (FY) |
2016-04-01 – 2019-03-31
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| Project Status |
Completed (Fiscal Year 2018)
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| Budget Amount *help |
¥18,980,000 (Direct Cost: ¥14,600,000、Indirect Cost: ¥4,380,000)
Fiscal Year 2018: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000)
Fiscal Year 2017: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000)
Fiscal Year 2016: ¥7,020,000 (Direct Cost: ¥5,400,000、Indirect Cost: ¥1,620,000)
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| 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 / 抗体作成 |
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| 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.
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| 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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Report
(4 results)
Research Products
(34 results)
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[Journal Article] Tetracyclic Truncated Analogue of the Marine Toxin Gambierol Modifies NMDA, Tau, and Amyloid β Expression in Mice Brains: Implications in AD Pathology2017
Author(s)
Eva Alonso, Andres C. Vieira, Ines Rodoriguez, Rebeca Alvarino, Sandra Gegunde, Haruhiko Fuwa, Yuto Suga, Makoto Sasaki, Amparo Alfonso, Jose Mannuel Cifuentes, Luis M. Botana
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Journal Title
ACS Chemical Neuroscience
Volume: 8
Issue: 6
Pages: 1358-1367
DOI
Related Report
Peer Reviewed / Int'l Joint Research
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[Book] 理科年表 20192018
Author(s)
佐々木 誠
Total Pages
17
Publisher
丸善出版株式会社
ISBN
9784621303320
Related Report
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[Book] 理科年表 平成302017
Author(s)
佐々木 誠
Total Pages
17
Publisher
丸善出版株式会社
ISBN
9784621302187
Related Report
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