Design and synthesis of 3D organic molecular architectures from self-assembly of helical foldamers conjugated to rigid linker

Abstract

The design and synthesis of artificial materials that mimic sophisticated and complex natural system is an important challenge in synthetic chemistry and biology. In this thesis, we designed a novel strategy for $C_3$-symmetric and $C_2$-symmetric building blocks which have conjugate secondary structures (i.e. tertiary structure) by connecting two or more peptide foldamers to a specific linker motif and obtained more complex hierarchical self-assembled structures from newly designed building blocks. We synthesized helix-linker-helix conjugated building blocks by connecting amide bonds with helical beta-peptide which is known to form stable 12-helical structure and benzene or alkene linker which has fixed orientation. We obtained foldectures from foldamer-conjugate building blocks by aqueous self-assembly and observed nanospheres, nanodiscs, and rectangular plates shapes at each building units. It means that the macroscopic 3D shapes of the foldectures changes as the structural parameters of foldamer-conjugate building blocks. We expect that the study of self-assembly of helix-linker-helix building units can play a key role to elucidate the information of hierarchical self-assembly of protein molecules.