Cyclic Poly(α-peptoid)s by Lithium bis(trimethylsilyl)amide (LiHMDS)-Mediated Ring-Expansion Polymerization: Simple Access to Bioactive Backbones
Pedro Salas‐Ambrosio, Antoine Tronnet, Marc Since, Sandra Bourgeade‐Delmas, Jean‐Luc Stigliani, Amélie Vax, Sébastien Lecommandoux, Bruno Dupuy, Pierre Verhaeghe, Colin Bonduelle
Abstract
Cyclic polymers display unique physicochemical and biological properties. However, their development is often limited by their challenging preparation. In this work, we present a simple route to cyclic poly(α-peptoids) from N-alkylated-N-carboxyanhydrides (NNCA) using LiHMDS promoted ring-expansion polymerization (REP) in DMF. This new method allows the unprecedented use of lysine-like monomers in REP to design bioactive macrocycles bearing pharmaceutical potential against Clostridioides difficile, a bacterium responsible for nosocomial infections.
Topics & Concepts
ChemistryPeptoidAmidePolymerizationLithium (medication)TrimethylsilylCombinatorial chemistryMonomerCyclic peptidePolymer chemistryRing (chemistry)Organic chemistryPolymerPeptideBiochemistryMedicineEndocrinologyChemical Synthesis and AnalysisClick Chemistry and ApplicationsAntimicrobial agents and applications