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An Orthogonal Dynamic Covalent Chemistry Tool for Ring-Opening Polymerization of Cyclic Oligochalcogenides on Detachable Helical Peptide Templates

Published inChemistry, vol. 28, no. 33, e202200785
Publication date2022-05-04
First online date2022-04-13
Abstract

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 310 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.

eng
Keywords
  • diselenides
  • disulfides
  • dynamers
  • orthogonal dynamic covalent chemistry
  • ring-opening dynamic covalent polymerization
  • templated polymerization
Research group
Citation (ISO format)
LAURENT, Quentin François Antoine, SAKAI, Naomi, MATILE, Stefan. An Orthogonal Dynamic Covalent Chemistry Tool for Ring-Opening Polymerization of Cyclic Oligochalcogenides on Detachable Helical Peptide Templates. In: Chemistry, 2022, vol. 28, n° 33, p. e202200785. doi: 10.1002/chem.202200785
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ISSN of the journal0947-6539
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Creation07/04/2022 2:45:00 PM
First validation07/04/2022 2:45:00 PM
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