Development and application of nanotubes based on polytheonamides

2001 Fiscal Year Final Research Report Summary

• Project/Area Number: 12556034
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 展開研究
• Research Field: Fisheries chemistry
• Research Institution: The University of Tokyo
• Principal Investigator: MATSUNAGA Shigeki Graduate School of Agricultural and Life Science, The University of Tokyo, Assoc. Prof., 大学院・農学生命科学研究科, 助教授 (60183951)
• Co-Investigator(Kenkyū-buntansha): OIKI Shigetoshi School of Medicine, Fukui Medical College Prof., 医学部, 教授 (10185176) ; MURAMATSU Ikunobu School of Medicine, Fukui Medical College Prof., 医学部, 教授 (10111965) ; FUSETANI Nobuhiro Graduate School of Agricultural and Life Science, The University of Tokyo, Prof., 大学院・農学生命科学研究科, 教授 (70012010)
• Project Period (FY): 2000 – 2001
• Keywords: marine sponge / peptide / structure elucidation / amino acid / polytheonamide / channel / ion channel

Research Abstract

In further structural study of polytheonamides, the candidates of the structures for the 44^<th> residue amino acid were synthesized. As the result, the structure of the pertinent resudue was concluded to be β,β-dimethylmethionine. This was confirmed by chemical reaction of polytheonamide B by oxidation and reduction. In the meantime, the structure of polytheonamide A was firmly established as a diastereomer differing in the configuration of the sulfur atom in the 44^<th> residue. The absolute stereochemistry of the 44^<th> residue was determined by BrCN reaction of polytheonamides affording the C-terminal lactone, and the following GC analysis on a chiral stationary phase.
Channel forming activity of polytheonamides were examined. Both polytheonamides A and B are incorporated into the lipid bilayer and conducted monovalent cations as does bacterial linear peptide gramicidin A. The channel formed by polytheonamides showed open and close state. The mechanism of this character needs further study.