The role of carbohydrates in biochemical processes is essential for living matter, because of their importance in signaling, energy (storage) and metabolism. Depending on their function, carbohydrates are included into larger constructs, such as proteins (glycoproteins), lipids (glycolipids) or other functionalities (glycoside). By mimicking these natural products based on synthetic constructs decorated with carbohydrates, it is possible to control biological interactions, such as cell uptake, specific interactions or interference with biochemical processes. To this end, one can use polymers that act as a carrier for the carbohydrate and in this work we have chosen poly(2-ethyl-2-oxazoline) (PEtOx). Such poly(2-alkyl-2-oxazoline)s (PAOx) are regarded as pseudo peptides because of their structural similarity to peptides. Moreover these polymers are invisible for the immune system, the so-called stealth effect, which is an important asset if they are used in the body. PAOx can be prepared by living cationic ring opening polymerization (CROP) of the 2-oxazoline monomer yielding well-defined polymers. Via partial hydrolysis of PEtOx, a copolymer of PEtOx and poly (ethylene imine) PEI is obtained. In the current work, we have exploited these PEtOx-PEI copolymers for the preparation of glycopolymers by reductive amination with the open forms of glucose and mannose. The aldehyde of the open for carbohydrates can attach to the secondary amines of PEI by imine formation, which is subsequently reduced to a stable tertiary amine. The ratio of PEtOx and carbohydrates is systematically varied and the glycoconjugates solution behavior is examined in detail by dynamic light scattering (DLS) revealing polymers that are present as unimers, polymers that exhibit lower critical solution temperature behavior and polymers that always agglomerate into microparticles.

Sweet polymers by combination of carbohydrates and poly(2-ethyl-2-oxazoline)s

248th National Meeting (2014)

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