Exosomes are 40-160 nm-sized vesicles secreted by most types of cells as vehicles for intercellular trafficking of cellular components. This property has stimulated a broad interest in exosomes as a natural drug vehicles. Recent research has highlighted the important role of exosome glycosylation in their biology, from their biosynthesis and cargo recruitment to their interaction with the recipient cell and their biodistribution. Considering the importance of glycans for exosome targeting capacity, we aim to produce exosomes as a potential tool for drug delivery in inflammatory and cancer therapy by glycoengineering their surface. We produced mesenchymal stem cell derived exosomes, known for their ability to modulate the immune system, and covalently attached sialyl LewisX tetrasaccharide, a molecule with high affinity to E-selectin, a lectin overexpressed in the endothelia of inflamed tissues and also tumors. We synthesized sialyl LewisX via a combination of chemical and chemo-enzymatic reactions. On the other hand, exosomes were purified, characterized and functionalized with different equivalents of the glycan. After checking the functionalization, the internalization of functionalised exosomes was studied using cells expressing E-selectin. For future work, the idea is to use these vesicles to perform in vivo biodistribution assays in inflammatory or metastatic mice model.