TY  - JOUR
A1  - Liebscher, Julia
A1  - Teßmar, Joerg Karl
A1  - Groll, Jürgen
T1  - In Situ Polymer Analogue Generation of Azlactone Functions at Poly(oxazoline)s for Peptide Conjugation
JF  - Macromolecular Chemistry and Physics
N2  - The physical and chemical stability of peptides for biomedical applications can be greatly enhanced through the conjugation of polymers. A well‐known but rather underemployed selective coupling functionality is the azlactone group, which readily reacts with a number of different nucleophiles without the need for activation and the formation of any by‐products. For example, azlactone functional polymers are used to react with peptides and proteins, rich in amino and thiol groups, to form polymeric beads for affinity‐based column chromatography. So far, side chain functional azlactone polymers have been mainly synthesized by radical polymerization using 2‐vinyl‐4,4‐dimethyl azlactone together with different acrylate monomers. Here, a new azlactone precursor equipped with a functional thiol is presented, which can be attached to any vinyl functional polymer by thiol–ene chemistry. Subsequently, the formation of the reactive azlactone ring can be performed in situ at high conversion rate without the need for illumination. This approach is tested on an azlactone side functional poly(2‐oxazoline) by coupling amine containing molecules including a model peptide and is proven via \(^1\)H NMR spectroscopy, IR spectroscopy, as well as HPLC measurements.
KW  - azlactone
KW  - peptide conjugation
KW  - polymer-analogue functionalization
KW  - polyoxazoline
Y1  - 2020
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-208147
VL  - 221
IS  - 1
ER  -