Chemoenzymatic synthesis of dendritic sialyl Lewisx

Add time:08/21/2019    Source:sciencedirect.com

Traditional structure activity relationship studies (SAR) have led to the development of numerous sialyl Lewisx analogs in the search for potential antiinflammatory agents. However, these methods do not take into account cluster or multivalent effects. Reported herein is the chemoenzymatic synthesis of di-, tetra-, and octa-valent sLex ligands scaffolded on dendrimers. Hypervalent l-lysine cores with covalently attached 2-acetamido-2-deoxy-d-glucose (N-acetylglucosamine, GlcNAc) residues were chemically prepared and enzymatically transformed into sLex-containing dendrimers so that multivalency, and its role in selectin-sLex interactions may be evaluated. This work constitutes another successful enzymatic synthesis of sLex and represents the first example of GlcNAc elongation on a synthetic dendrimer scaffold. These sLex dendrimers are currently being investigated as selectin antagonists.

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