Side-chain cysteine-functionalized poly(2-oxazoline)s for multiple peptide conjugation by native chemical ligation

Biomacromolecules
Michael SchmitzJürgen Groll

Abstract

We prepared statistical copolymers composed of 2-methyl-2-oxazoline (MeOx) in combination with 2-butenyl-2-oxazoline (BuOx) or 2-decenyl-2-oxazoline (DecOx) as a basis for polymer analogous introduction of 1,2-aminothiol moieties at the side chain. MeOx provides hydrophilicity as well as cyto- and hemocompatibility, whereas the alkene groups of BuOx and DecOx serve for functionalization with a thiofunctional thiazolidine by UV-mediated thiol-ene reaction. After deprotection the cysteine content in functionalized poly(2-oxazoline) (POx) is quantified by NMR and a modified trinitrobenzenesulfonic acid assay. The luminescent cell viability assay shows no negative influence of cysteine-functionalized POx (cys-POx) concerning cell viability and cell number. cys-POx was used for multiple chemically orthogonal couplings with thioester-terminated peptides through native chemical ligation (NCL), which was performed and confirmed by NMR and MALDI-ToF measurements.

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Citations

Jan 12, 2016·Biomacromolecules·Kristi S Anseth, Harm-Anton Klok
Jan 13, 2016·Macromolecular Bioscience·Jonas F NawrothRobert Luxenhofer
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Jun 28, 2017·Biomacromolecules·Thomas LorsonRobert Luxenhofer
Feb 2, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Stéphane W DuchironLuc Avérous
May 8, 2018·Macromolecular Bioscience·Tim R DargavilleRichard Hoogenboom
Apr 8, 2020·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Julia BlöhbaumJürgen Groll
Dec 7, 2018·Journal of the American Chemical Society·Bart VerbraekenRichard Hoogenboom
Jul 24, 2018·Langmuir : the ACS Journal of Surfaces and Colloids·Pei TangJulien E Gautrot

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