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Updated: Jul 13, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Fit to be tied: conformation-directed macrocyclization of peptoid foldamers
Justin M Holub1, Hangjun Jang, Kent Kirshenbaum
1Department of Chemistry, New York University, 100 Washington Square East, New York, New York 10003-6688, USA.
Abstract:
Covalent macrocyclic constraints can be readily installed on N-substituted glycine "peptoid" oligomer substrates. Cu(I)-catalyzed [3+2] cycloaddition reactions were conducted on solid support to ligate peptoid side chain azide and alkyne functionalities. Intramolecular macrocycle formation is facilitated by preorganizing the reactive groups across one turn of the helical secondary structure. These results confirm that conformational ordering can be exploited to assist the macrocyclization of folded oligomers.
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