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Updated: Jul 1, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Building functionalized peptidomimetics: use of electroauxiliaries for introducing N-acyliminium ions into peptides
Haizhou Sun1, Connor Martin, David Kesselring
1Department of Chemistry, Washington University, St. Louis, Missouri 63130, USA.
Abstract:
A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.
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