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Updated: Jun 24, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Reversible transformation between rings and coils in a dynamic hydrogen-bonded self-assembly
Shiki Yagai1, Shun Kubota, Hikaru Saito
1Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan. yagai@faculty.chiba-u.jp
Abstract:
Several proteins, such as tobacco mosaic virus coat protein and the beta protein of the bacteriophage lambda, are known to exhibit unique dynamic self-organization processes involving ring-shaped and extended helical nanostructures triggered by chemical stimuli. However, transformation of rings into coils as observed in biological assemblies has never been realized with synthetic molecular building blocks. Oligo(p-phenylenevinylene) functionalized on one end with barbituric acid and on the other end with aliphatic tails self-organizes in aliphatic solvents to form nanorings through hydrogen-bonding and pi-stacking interactions. Upon an increase in concentration, the nanorings transform into rodlike nanostructures, which are considered to be formed through helically coiled objects consisting of quasi-one-dimensional fibers.
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