Award type：Award from Japanese society, conference, symposium, etc. 

Award type：Award from Japanese society, conference, symposium, etc. 

Language：Japanese   Publisher：The Society of Synthetic Organic Chemistry, Japan  

<p>Highly strained cyclic compounds such as arynes and cyclic alkynes are important building blocks in organic synthesis. However, cyclic allenes have received far less attention. Herein, recent progress in the cycloaddition reaction using highly strained 6-membered allenes will be discussed.</p>

DOI： 10.5059/yukigoseikyokaishi.82.63

CiNii Research

Language：English   Publisher：Toxicon  

Tetrodotoxin (TTX) is a potent neurotoxin that binds to voltage-gated sodium channels and blocks the passage of sodium ions. TTX is widely distributed in both terrestrial and marine organisms, and the toxic puffers are believed to accumulate TTX through the food chain. Although pufferfish was previously thought to be attracted by TTX, recent finding from electroolfactogram (EOG) studies have indicated that the olfactory epithelium of T. alboplumbeus responded to 5, 6, 11-trideoxyTTX (TDT), but not to TTX itself. In this study, we examined behavioral experiments for Takifugu rubripes to distinguish between TTX and TDT under static and flow-through conditions. Our data clearly suggested that T. rubripes juveniles were attracted to TDT, not TTX. Moreover, we determined that the minimum effective dose of TDT to attract the puffer was 1–2 nmol of TDT under static conditions and 50–60 nmol of TDT under flow-through conditions. Following the experiments under static conditions, numerous bite marks by the pufferfish were found solely on the agarose gel infused with TDT. Based on these finding, we hypothesize that the pufferfish are attracted to TDT derived from prey, leading them effectively become toxic.

DOI： 10.1016/j.toxicon.2023.107539

Web of Science

Scopus

PubMed

Language：Japanese   Publisher：Journal of Organic Chemistry  

The collective synthesis of the four spiro-cyclic guanidines Tb-210B, Tb-226, Tb-242C, and Tb-258, all of which have been isolated from puffer fish and are considered possible biosynthetic intermediates of tetrodotoxin, has been achieved. Our synthesis is based on the stepwise deoxygenation or hydroxylation of a common intermediate, prepared from a known oxazoline.

DOI： 10.1021/acs.joc.2c00704

Web of Science

Scopus

PubMed

Language：Japanese   Publisher：Organic Letters  

Despite decades of research, the biosynthesis of tetrodotoxin, also known as a puffer fish toxin, remains an unsolved mystery. We disclose a synthesis of the 8-deoxy analogue of 4,9-anhydro-10-hemiketal-5-deoxy-tetrodotoxin, a possible biosynthetic precursor of tetrodotoxin isolated from the Japanese toxic newt, by an intramolecular radical cyclization of a known starting material.

DOI： 10.1021/acs.orglett.1c03565

Web of Science

Scopus

PubMed

Language：English   Publishing type：Research paper (scientific journal)  

DOI： doi.org/10.1002/anie.202007280

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：広島  

Event date： 2020.11

Language：Japanese   Presentation type：Poster presentation  

Venue：愛知   Country：Japan  

Language：Japanese   Presentation type：Poster presentation  

Venue：静岡・オンライン  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：仙台・オンライン  

Language：Japanese   Presentation type：Oral presentation (general)  

Venue：京都   Country：Japan