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Cyclic Poly(α-peptoid)s by Lithium bis(trimethylsilyl)amide (LiHMDS)-Mediated Ring-Expansion Polymerization: Simple Access to Bioactive Backbones

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.
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https://hal.archives-ouvertes.fr/hal-03173586
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Submitted on : Thursday, March 18, 2021 - 3:33:06 PM
Last modification on : Thursday, December 2, 2021 - 2:10:04 PM
Long-term archiving on: : Monday, June 21, 2021 - 8:46:18 AM

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Pedro Salas-Ambrosio, Antoine Tronnet, Marc Since, Sandra Bourgeade-Delmas, Jean-Luc Stigliani, et al.. Cyclic Poly(α-peptoid)s by Lithium bis(trimethylsilyl)amide (LiHMDS)-Mediated Ring-Expansion Polymerization: Simple Access to Bioactive Backbones. Journal of the American Chemical Society, American Chemical Society, 2021, 143 (10), pp.3697-3702. ⟨10.1021/jacs.0c13231⟩. ⟨hal-03173586⟩

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