Design of anti-freezing molecules based on fluoro-sulfur functionalized terphenyl and bicyclo(1.1.1)pentane skeletons

2020 Fiscal Year Final Research Report

• Project/Area Number: 19K22491
• Research Category: Grant-in-Aid for Challenging Research (Exploratory)
• Allocation Type: Multi-year Fund
• Review Section: Medium-sized Section 47:Pharmaceutical sciences and related fields
• Research Institution: Nagoya Institute of Technology
• Principal Investigator: Shibata Norio 名古屋工業大学, 工学(系)研究科(研究院), 教授 (40293302)
• Project Period (FY): 2019-06-28 – 2021-03-31
• Keywords: ヘリックス / テルフェニル / 不凍活性 / 糖 / ビアリール化 / テトラフルオロスルファニル / フッ素 / グアニジン

Outline of Final Research Achievements

The anti-freezing molecules have gained much attention in the fields of food, cosmetic and medical sciences. They are generally found in nature, but artificial anti-freezing molecules are scarce. We herein attempted the design and synthesized of small organic compounds having anti-freezing activity. Our idea bases on the mimics of the α-helix structure by molecular steric hindrance without hydrogen bonding. Thus two types of anti-freezing molecules having a 3D-α-helix skeleton were designed, such as terphenyl compounds and aryl-tetrafluorosulfanyl-alkenyl compounds. First, terphenyl compounds introducing water-soluble guanidine into the side chain were synthesized via multi-steps including, twice biarylation reactions. Excitingly, the compounds synthesized exhibited antifreeze activity. We also successfully synthesized molecules incorporating a tetrafluorosulfanyl structure with a sulfur fluoride functional group and three units of aromatics and alkynes.

Free Research Field

有機フッ素化学

Academic Significance and Societal Importance of the Research Achievements

不凍分子は幅広い産業へ応用が期待されている。しかし現実にはその源を天然物に頼らざるを得ないため入手に問題であり，その利用は極めて限定されている。そのため人工不凍作用物質の開発が望まれている。本研究成果は，遅々として進まなかった人工不凍分子開発の足がかりとなるものである。小分子でもヘリックス構造と水溶性構造があれば，不凍作用を示す可能性を初めて明らかにしたことにより，今後の開発に拍車がかかると予測される。