Poly(2-ethyl-2-oxazoline) Featuring a Central Amino Moiety

Dirauf, Michael; Fritz, Nicole; Gottschaldt, Michael; Weber, Christine; 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.

Year:

2021

Type of Publication:

Article

Journal:

Macromolecular Chemistry and Physics

Volume:

42

Pages:

2100132

DOI:

https://doi.org/10.1002/marc.202100132