Efficient Synthesis of Muramic and Glucuronic Acid Glycodendrimers as Potent Dengue Virus Antagonists

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1st EuroCarb Young Researcher (ECYR) Workshop

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Mini symposium: Glycobiology at the LUMC and beyond

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Efficient Synthesis of Muramic and Glucuronic Acid Glycodendrimers as Potent Dengue Virus Antagonists

Maria J Hernaiz 1 , Algredo H Cabanillas 2 , García-Oliva Cecilia 1 , Pilar Hoyos 1 , Almudena Perona 1 , Angel Rumbero 2

1 Complutense University, Madrid, Spain, 2 Autonoma University , Madrid, Spain

Carbohydrates are involved in many important pathological processes, such as bacterial and viral infections. Most of these activities depend on carbohydrate-protein interactions. Biomolecules exhibit multiple carbohydrates, which stablish multivalent interactions increasing the binding strengths to proteins [1]. In this work, we present the preparation of novel glucuronic and muramic acid glycodendrimers as potential active compounds in the treatment of Dengue virus [2]. In a first step we prepared three aromatic scaffolds functionalized with a terminal dialkyne, trialkyne and tetraalkyne, as well as muramic and glucuronic acid derivatives, functionalized with an azide group through optimized synthetic strategies. Those carbohydrate derivatives were coupled to scaffold etinyl groups by click chemistry, affording the desired glycodendrimers with high yields and under sustainable conditions.

In addition, enzymatic approaches have been explored in order to achieve new disaccharides based on those structures. In this way, different commercial glycosidases were screened, employing N-acetylglucosamine as acceptor and the muramic and glucuronic acids derivatives as donors in the presence of green solvents.

Finally Surface Plasmon Resonance (SPR) studies have demonstrated that the new glycodendrimers obtained bind efficiently to the Dengue virus envelope protein. These interactions have been also simulated and explained by molecular modelling studies. These studies confirm that efficient chemical synthesis of glycodendrimers can be brought easily offering a versatile strategy to find new active compounds again Dengue virus.

Preparation of muramic acid and glucuronic acid glycodendrimers

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