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Updated: Jan 8, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
N-to-C peptide elongation by ammonia-Ugi reaction: synthesis of potent self-assembling elastin-like short peptides
Keisuke Tomohara1,2, Naoki Tanaka3, Yukino Kotake1
1Faculty of Pharmaceutical Sciences, Kyoto Pharmaceutical University, 1 Misasagishichono-cho, Yamashina-ku, Kyoto 607-8412, Japan. tomohara47@mb.kyoto-phu.ac.jp.
Abstract:
The ammonia-Ugi reaction employing ammonium carboxylates of N-protected amino acids (or peptides), ketones, and α-isocyano esters enabled N-to-C peptide elongation, together with in situ construction of α,α-disubstituted amino acid residues. This method offered an effective synthetic method of novel elastin-like short peptides, which exhibited highly potent self-assembling properties.
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The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
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