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  1. Laurent, Q.; Sakai, N.; Matile, S. “An Orthogonal Dynamic Covalent Chemistry Tool for Ring-Opening Polymerization of Cyclic Oligochalcogenides on Detachable Helical Peptide Templates” Chem. Eur. J. 2022, 28, e202200785

A model system is introduced as a general tool to elaborate on orthogonal templation of dynamic covalent ring-opening polymerization (ODC-TROP).  The tool consists of 3 10 helical peptides as unprecedented templates and semicarbazones as orthogonal dynamic covalent linkers.  With difficult-to-control 1,2-dithiolanes, ODC-TROP on the level of short model oligomers occurs with high templation efficiency, increasing and diminishing upon helix stabilization and denaturation, respectively.  Further, an anti-templated conjugate with mispositioned monomers gave reduced templation upon helix twisting.  Even with the “unpolymerizable” 1,2-diselenolanes, initial studies already afford mild templation efficiency.  These proof-of-principle results promise that the here introduced tool, recyclable and enabling late-stage side chain modification, will be useful to realize ODC-TROP of intractable or unknown cyclic dynamic covalent monomers for dynamer materials as well as cellular uptake and signaling applications.

DOI: 10.1002/chem.202200785 

open archive unige:161908 • pdf