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Updated: Oct 11, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Automation of the Azapeptide Submonomer Synthesis Method
Tyler G Hobart1, Molly E Helton1, Maxwell O Bowles1
1Department of Chemistry, North Carolina State University, Raleigh, North Carolina, USA.
Abstract:
The automation of the azapeptide submonomer synthesis procedure is reported. All steps for on-resin aza-amino acid synthesis, including semicarbazone incorporation, alkylation, deprotection, and semicarbazide acylation were adapted for use on a commercially available peptide synthesizer. Key requirements for success included the use of a stable isocyanate precursor for the semicarbazone installation, the use of stable reagents in DMF, and elimination of cooling steps. The synthesis of > 30 azapeptides was accomplished using our optimized automated submonomer azapeptide synthesis procedure.
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