April 15, 2019
Journal Article

Solid-Phase Synthesis of Three-Armed Star-Shaped Peptoids and Their Hierarchical Self-Assembly

Abstract

Due to the branched structure feature and unique properties, a variety of star-shaped polymers have been designed and synthesized. Despite those advances, solid-phase synthesis of star-shaped sequence-defined synthetic polymers that exhibit hierarchical self-assembly remains a significant challenge. Hence, we present an effective strategy for the solid-phase synthesis of three-armed star-shaped peptoids, in which ethylenediamine was used as the centric star pivot. Based on the sequence of monomer addition, a series of AA'A''-type and ABB'-type peptoids were synthesized and characterized by UPLC-MS (ultra-high performance liquid chromatography-mass spectrometry). By taking advantage of the easy-synthesis and large side-chain diversity, we synthesized star-shaped peptoids with tunable functions. We further demonstrated the aqueous self-assembly of some representative peptoids into biomimetic nanomaterials with well-defined hierarchical structures, such as nanofibers and nanotubes. These results indicate that star-shaped peptoids offer the potential in self-assembly of biomimetic nanomaterials with tunable chemistries and functions.

Revised: July 3, 2019 | Published: April 15, 2019

Citation

Jin H., T. Jian, Y. Ding, Y. Chen, P. Mu, L. Wang, and C. Chen. 2019. Solid-Phase Synthesis of Three-Armed Star-Shaped Peptoids and Their Hierarchical Self-Assembly. Biopolymers 110, no. 4:e23258. PNNL-SA-140649. doi:10.1002/bip.23258