Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 28, Issue 33, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202200785
Keywords
diselenides; disulfides; dynamers; orthogonal dynamic covalent chemistry; ring-opening dynamic covalent polymerization; templated polymerization
Categories
Funding
- University of Geneva
- National Centre for Competence in Research (NCCR) Chemical Biology
- NCCR Molecular Systems Engineering
- Swiss NSF [200020 204175, 51NF40-185898, 51NF40182895]
- Universite de Geneve
- Swiss National Science Foundation (SNF) [200020_204175, 51NF40-185898] Funding Source: Swiss National Science Foundation (SNF)
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A model system is introduced as a tool for orthogonal templation of dynamic covalent ring-opening polymerization. The tool shows high templation efficiency at the level of short model oligomers and promises to be useful for intractable or unknown cyclic dynamic covalent monomers.
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.
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