Preparation of oligopeptides with lipophilic ionpairs and control of solubility in organic solvents

2015 Fiscal Year Final Research Report

• Project/Area Number: 26620091
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Polymer chemistry
• Research Institution: Hokkaido University
• Principal Investigator: SADA KAZUKI 北海道大学, 理学(系)研究科(研究院), 教授 (80225911)
• Co-Investigator(Kenkyū-buntansha): KOKADO KENTA 北海道大学, 大学院理学研究院, 助教 (40600226)
• Project Period (FY): 2014-04-01 – 2016-03-31
• Keywords: イオン対 / オリゴペプチド / 生体機能利用 / 分子認識 / イオン解離 / 可溶化

Outline of Final Research Achievements

In this research project, we investigated incorporation of tetraalkylammonium tetraphenylborate as a lipophilic ionpair into some lipophilic oligopeptide chains and enhancement of solubility in less polar media by introducing the ionpair. FMOC solid-state synthesis provided oligopeptides with 5-13 amino acid with one or two acetylenic residues. Then, click reaction between these oligopeptides and azide-modified tetraalkylammonium tetraphenylborate gave the oligopeptides. ESI-mass spectrometry clearly indicated introduction of tetraphenylborate tetraalkylaamonium ionpair. They were soluble in 1,2-dicholroethane and solubility of the oligopeptides with this ionpair increased compared to that of the unmodified oligopeptides. Therefore, incorporation of the lipophilic ionpair should contribute to solubility due to electrostatic repulsion and osmotic pressure.

Free Research Field

超分子化学