Cyclic Poly(α-peptoid)s by Lithium bis(trimethylsilyl)amide (LiHMDS)-Mediated Ring-Expansion Polymerization: Simple Access to Bioactive Backbones
- 2 March 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 143 (10), 3697-3702
- https://doi.org/10.1021/jacs.0c13231
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(alpha-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.Funding Information
- Agence Nationale de la Recherche (ANR-17-CE07-0039-01)
This publication has 34 references indexed in Scilit:
- The synthesis, properties and potential applications of cyclic polymersNature Chemistry, 2020
- Tuneable enhancement of the salt and thermal stability of polymeric micelles by cyclized amphiphilesNature Communications, 2013
- Topology-Directed Control on Thermal Stability: Micelles Formed from Linear and Cyclized Amphiphilic Block CopolymersJournal of the American Chemical Society, 2010
- Cyclic polymers: Synthetic strategies and physical propertiesJournal of Polymer Science Part A: Polymer Chemistry, 2009
- Synthesis and Degradation Behavior of Cyclic Poly(ε-caprolactone)Macromolecules, 2009
- Synthetic approaches for the preparation of cyclic polymersChemical Society Reviews, 2009
- Controlled ring-opening polymerisation of cyclic esters: polymer blocks in self-assembled nanostructuresChemical Communications, 2008
- Zwitterionic Polymerization of Lactide to Cyclic Poly(Lactide) by Using N‐Heterocyclic Carbene OrganocatalystsAngewandte Chemie, 2007
- Scattering Properties of Rod−Coil and Once-Broken Rod Block CopolymersMacromolecules, 2001
- Static and dynamic scattering from cyclic diblock copolymer chains in solutionMacromolecular Symposia, 1994