?Glycopolymers with pendant carbohydrates on a polypeptide backbone, therefore named glycopolypeptides, are a new class of biomimetic materials inspired by natural glycoproteins. The preparation of these polymers involves recent progresses made with N-carboxyanhydride (NCA) controlled ring-opening polymerization (ROP)as well as efficient chemical ligation (�click chemistry�). The purpose of glycopolypeptides is to mimic the chemical structure of glycoproteins to better understand, by using a simplified model, physicochemical or biological properties of natural glycoproteins and then, to take advantage of the fundamental principles of their structure�function relationships. Herein, we present two methodologies to synthesize linear or tree-like amphiphilic macromolecules fully based on amino acid and carbohydrate building blocks by using the chemical ligation of different kinds of saccharides onto polypeptidic backbones obtained by polymer chemistry. (1,2) These biomimetic materials have presented interesting self-assembly behaviours in solution leading to nanoparticles with sizes below 100 nm and displaying sugars moieties at their surface. Among these nanoparticles, glycopeptosomes were observed: these vesicles are interesting synthetic mimic of viruses. (3) Lectins targeting was therefore achieved with different nanomaterials made of glycopolypeptides to interact with sugar-binding proteins involved in serious disease such as AIDS or cancer.REFERENCES 1- C. Bonduelle et al., Chem. Commun., 2012, 48 , 8353-8355.2- J. Huang et al. J. Am. Chem. Soc., 2012, 134 , 119-122.3- C. Schatz et al. Angew. Chem. Int. Ed., 2009, 48 , 2572-2575

Synthetic glycopolypeptides as biomimetic analogs of natural glycoproteins

246th National Meeting (2013)

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