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Synthesis and structure of novel potentially bioactive amphiphilic -O-(N)-glycosides

Carbohydrate-based surfactants are molecules with a sugar hydrophilic moiety and a hydrophobic tail, usually a hydrocarbon chain such as a fatty acid or alcohol. These glycosides have been synthesized and their structures were analyzed in terms of supramolecular arrangements as we see in recent literature. Also, they were proposed as potential therapeutic active molecules. The capability to interact with the lipid bilayer of biological membranes bring them a bioactive profile. In this presentation, we show the design and synthesis of carbohydrate derivatives with amphiphilic properties including a bioactive moiety, a Schiff base. Oxime ether function is an important structural motif in many famous drug scaffolds. Many anti-viral agents have the -C=N-O- function in their structures, for example, the kinase inhibitor "enviroxime" and the recently reported "EIDD-2801" glycoside that has shown broad anti-influenza virus activity. We present here the synthesis and structural analysis of novel -O-(N)-glycosides. The reaction of NHS with penta-O-acetyl-D-glucose or galactose in the presence of BF3.OEt2 gives the b anomer glycoside in a straightforward manner. Further hydrazinolysis and condensation with decanal give the desired products. Their complete structures, including the anomeric and E/Z double bond configurations, were determined by spectroscopic analysis.

Keywords: amphiphilic carbohydrates; -O-(N)-glycosides; NMR