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Updated: May 17, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Bending rigid molecular rods: formation of oligoproline macrocycles
Conor C G Scully1, Vishal Rai, Gennadiy Poda
1Davenport Research Laboratories, Department of Chemistry, University of Toronto, Ontario, Canada.
Abstract:
Bent but not broken: cyclic oligoprolines are accessed in a reaction that effectively bends rigid oligoproline peptides (see scheme; TBDMS=tert-butyldimethylsilyl). The stitching is accomplished during macrocyclization enabled by aziridine aldehydes and isocyanides. Molecular modeling studies suggest that electrostatic attraction between the termini of the linear peptide is pivotal for macrocyclization. The macrocycles were studied by circular dichroism with a polyproline II structure being observed in larger macrocycles.
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