@article{BorovaSchluttNickeletal.2022,
  author    = {Borova, Solomiia and Schlutt, Christine and Nickel, Joachim and Luxenhofer, Robert},
  title     = {A Transient Initiator for Polypeptoids Postpolymerization α-Functionalization via Activation of a Thioester Group},
  series = {Macromolecular Chemistry and Physics},
  volume    = {223},
  journal   = {Macromolecular Chemistry and Physics},
  number    = {3},
  doi       = {10.1002/macp.202100331},
  url       = {http://nbn-resolving.de/urn:nbn:de:bvb:20-opus-257587},
  year      = {2022},
  abstract  = {Here, a postpolymerization modification method for an α-terminal functionalized poly-(N-methyl-glycine), also known as polysarcosine, is introduced. 4-(Methylthio)phenyl piperidine-4-carboxylate as an initiator for the ring-opening polymerization of N-methyl-glycine-N-carboxyanhydride followed by oxidation of the thioester group to yield an α-terminal reactive 4-(methylsulfonyl)phenyl piperidine-4-carboxylate polymer is utilized. This represents an activated carboxylic acid terminus, allowing straightforward modification with nucleophiles under mild reaction conditions and provides the possibility to introduce a wide variety of nucleophiles as exemplified using small molecules, fluorescent dyes, and model proteins. The new initiator yielded polymers with well-defined molar mass, low dispersity, and high end-group fidelity, as observed by gel permeation chromatography, nuclear magnetic resonance spectroscopy, and matrix-assisted laser desorption/ionization time-of-flight mass spectroscopy. The introduced method can be of great interest for bioconjugation, but requires optimization, especially for protein conjugation.},
  language  = {en}
}