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Updated: May 16, 2025

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
A Modular and Scalable Route to Protected Cyclopropane Amino Acid Building Blocks
Charlie T Swan1, Alex G Edmonds1, Stephen P Argent1
1School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, United Kingdom.
Abstract:
An improved method for the synthesis of noncanonical cyclopropane amino acids from common laboratory reagents is described, avoiding the use of neurotoxic oxidants or precious metal catalysts. Intramolecular isocyanate trapping via a Hofmann rearrangement permits the synthesis of bicyclic carbamates in an enantioenriched and diastereopure manner. Subsequent ring-opening of these species allows access to cyclopropane amino acids which can be further functionalized via oxidation and SN2 pathways and incorporated into peptides via solid-phase peptide synthesis.
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