Back
Synthesis of Polymers Containing Potassium Acyltrifluoroborates (KATs) and Post-polymerization Ligation and Conjugation.
Journal article

Synthesis of Polymers Containing Potassium Acyltrifluoroborates (KATs) and Post-polymerization Ligation and Conjugation.

  • Schauenburg D Laboratorium für Organische Chemie, Department of Chemistry and Applied biosciences, ETH Zürich, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.
  • Divandari M Laboratory for Surface Science and Technology, Department of Materials, ETH Zurich, Vladimir-Prelog-Weg 5, 8093, Zürich, Switzerland.
  • Neumann K Laboratorium für Organische Chemie, Department of Chemistry and Applied biosciences, ETH Zürich, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.
  • Spiegel CA Laboratorium für Organische Chemie, Department of Chemistry and Applied biosciences, ETH Zürich, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.
  • Hackett T Laboratory for Surface Science and Technology, Department of Materials, ETH Zurich, Vladimir-Prelog-Weg 5, 8093, Zürich, Switzerland.
  • Dzeng YC Laboratorium für Organische Chemie, Department of Chemistry and Applied biosciences, ETH Zürich, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.
  • Spencer ND Laboratory for Surface Science and Technology, Department of Materials, ETH Zurich, Vladimir-Prelog-Weg 5, 8093, Zürich, Switzerland.
  • Bode JW Laboratorium für Organische Chemie, Department of Chemistry and Applied biosciences, ETH Zürich, Vladimir-Prelog-Weg 3, 8093, Zürich, Switzerland.
Show more…
  • 2020-05-08
Published in:
  • Angewandte Chemie (International ed. in English). - 2020
ATRP
KAT ligation
RAFT
antibiotics
post-polymerization modification
English We report the synthesis of monomers for atom-transfer radical polymerization (ATRP) and a reversible addition-fragmentation chain transfer (RAFT) agent bearing trifluoroborate iminiums (TIMs), which are quantitatively converted into potassium acyltrifluoroborates (KATs) after polymerization. The resulting KAT-containing polymers are suitable for rapid amide-forming ligations for both post-polymerization modification and polymer conjugation. The polymer conjugation occurs rapidly, even under dilute (micromolar) aqueous conditions at ambient temperatures, thereby enabling the synthesis of a variety of linear and star-shaped block copolymers. In addition, we applied post-polymerization modification to the covalent linking of a photocaged cyclic antibiotic (gramicidin S) to the side chains of the KAT-containing copolymer. Cellular assays revealed that the polymer-antibiotic conjugate is biocompatible and provides efficient light-controlled release of the antibiotic on demand.
Language
  • English
Open access status
closed
Identifiers
Persistent URL
https://sonar.ch/global/documents/283443
Statistics
Document views: 21 File downloads: