Synthetic glycopolymers are promising candidates for biomedical applications and for investigation of carbohydrate-protein interactions [1]. Polypeptide-based glycopolymers are under investigation as structural mimics of natural glycoproteins with their ability to form secondary structures. Especially stimuli-responsive structural switches are very attractive for the design of �smart� polymeric materials. We have combined the versatility and stimuli-responsiveness of a well-known pH-sensitive polypeptide, i.e. poly(a,L-glutamic acid) (PGA), with the biological activity of sugars by direct glycosylation of PGA. For the synthesis we used a facile aqueous amide coupling approach, where the coupling reaction is conducted in water without any buffer or additive except for the coupling agent itself [2]. Thus the sugar density can be adjusted very easily. This coupling strategy has the potential to be applied to already existing polymeric architectures and materials containing PGA.We studied the secondary structure (e.g. the helix-coil transition), the aggregation behavior and the biological activity of different partially glycosylated PGAs. Circular dichroism (CD) spectroscopy revealed a strong correlation between sugar density and helicity. Preliminary tests for the biological activity demonstrated specific binding of the glycopolypeptides with lectins. Further lectin binding tests were carried out using a quartz crystal microbalance with dissipation monitoring (QCM-D).This work was supported by the IUPAC Transnational Call in Polymer Chemistry and the German Research Foundation (DFG)[1] S.G. Spain, N.R. Cameron, Polym. Chem. 2011  , 2, 60-68.[2] R. Mildner, H. Menzel, J. Polym. Sci. Part A: Polym. Chem. 2013  , 51, 3925-3931.

pH-Responsive, synthetic glycopolypeptides and their interaction with lectins

247th National Meeting (2014)

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