An Orthogonal Dynamic Covalent Chemistry Tool for Ring-Opening Polymerization of Cyclic Oligochalcogenides on Detachable Helical Peptide Templates.
Chemistry
; 28(33): e202200785, 2022 Jun 10.
Article
em En
| MEDLINE
| ID: mdl-35416345
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.
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MEDLINE
Assunto principal:
Peptídeos
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article