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Updated: Sep 17, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Azapeptide Atropisomers From Late-Stage N-Alkylations
Molly E Helton1, Christopher S Howard1, Keisy Prieto Bruno1
1Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, United States.
None:
We evaluate peptide sequence compatibility during late-stage azapeptide N-alkylation reactions and describe the atropisomeric properties of the azapeptoid and N1,N2-dialkylated azapeptide products. Our findings indicate that almost all protected amino acid side chains are compatible with the late-stage alkylation conditions on resin, with the exception of methionine. Using variable temperature NMR and dynamic HPLC, N-N rotational energy barriers of 15-16 and 20-24 kcal/mol are reported for a series of azapeptoids (monoalkylated) and N1,N2-dialkylated azapeptides, respectively.
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