Responsive Glyco-Poly(2-oxazoline)s: Synthesis, Cloud Point Tuning and Lectin Binding

Kempe, Kristian; Weber, Christine; Babiuch, Krzysztof; Gottschaldt, Michael; Hoogenboom, Richard; Schubert, Ulrich S.

Abstract:

A new sugar-substituted 2-oxazoline monomer was prepared using the copper-catalyzed alkyne-azide cycloaddition (CuAAC) reaction. Its copolymerization with 2-ethyl-2-oxazoline as well as 2-(dec-9-enyl)-2-oxazoline, yielding well-defined copolymers with the possibility to tune the properties by thiol–ene “click” reactions, is described. Extensive solubility studies on the corresponding glycocopolymers demonstrated that the lower critical solution temperature behavior and pH-responsiveness of these copolymers can be adjusted in water and phosphate-buffered saline (PBS) depending on the choice of the thiol. By conjugation of 2,3,4,6-tetra-O-acetyl-1-thio-β-d-glucopyranose and subsequent deprotection of the sugar moieties, the hydrophilicity of the copolymer could be increased significantly, allowing a cloud-point tuning in the physiological range. Furthermore, the binding capability of the glycosylated copoly(2-oxazoline) to concanavalin A was investigated.

Year:

2011

Type of Publication:

Article

Journal:

Biomacromolecules

Volume:

12

Pages:

2591 - 2600