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Updated: Jun 17, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Double-stranded supramolecular assembly through salt bridge formation between rigid and flexible amidine and
Hiroki Iida1, Munenori Shimoyama, Yoshio Furusho
1Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan.
Abstract:
A series of monomeric strands consisting of m-terphenyl backbones with chiral rigid C-linked (3) and flexible N-linked (5) formamidines and achiral carboxylic acid (4) and flexible carboxymethyl (6) residues were synthesized, and their duplex formations through amidinium-carboxylate salt bridges were investigated by NMR, circular dichroism (CD), and UV-visible spectroscopies. The salt bridge-derived duplex formation was largely dependent on the structures of the formamidine and carboxylic acid strands, and the C-linked formamidine strand 3 formed a more stable duplex with the complementary carboxylic acid strands (4 and 6) than did the flexible N-linked formamidine strand 5. The single crystal X-ray analysis revealed that the duplex 5.4 has a skewed right-handed double helical structure. A complementary duplex dimer was also synthesized from the dimers of 5 and 4 joined by diacetylene linkers. Variable-temperature CD measurements indicated that the duplex possesses a dynamic double helical structure resulting from the flexible N-linked formamidine units.
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