Poly(2‐ethyl‐2‐oxazoline) featuring a central amino moiety

GND
1258308029
Affiliation
Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena
Dirauf, Michael;
Affiliation
Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena
Fritz, Nicole;
GND
123955769
ORCID
0000-0003-4210-2956
Affiliation
Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena
Gottschaldt, Michael;
GND
1027788505
ORCID
0000-0003-0712-5255
Affiliation
Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena
Weber, Christine;
GND
113792077
ORCID
0000-0003-4978-4670
Affiliation
Laboratory of Organic and Macromolecular Chemistry (IOMC), Friedrich Schiller University Jena
Schubert, Ulrich S.

Abstract The incorporation of an amino group into a bifunctional initiator for the cationic ring‐opening polymerization (CROP) is achieved in a two‐step reaction. Detailed kinetic studies using 2‐ethyl‐2‐oxazoline demonstrate the initiators’ eligibility for the CROP yielding well‐defined polymers featuring molar masses of about 2000 g mol –1 . Deprotection of the phthalimide moiety subsequent to polymerization enables the introduction of a cyclooctyne group in central position of the polymer which is further exploited in a strain‐promoted alkyne‐azide click reaction (SpAAC) with a Fmoc‐protected azido lysine representing a commonly used binding motif for site specific polymer–protein/peptide conjugation. In‐depth characterization via electrospray ionization mass spectrometry (ESI) confirms the success of all post polymerization modification steps.

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