Abstract
Sialic acids are glycans with importance in normal functioning and multiple disease states such as cancer. Unfortunately, the glycosidic bonds connecting sialic acids together or to other sugars are labile and can break down under relatively mild conditions. Herein we report the green solution phase synthesis of glycomimetics of oligosialic acid containing N-acylhydrazide inter-residue linkages. These glycomimetics are resistant to both acid/base-catalyzed and enzyme-mediated degradation. Because of this stability, these oligosaccharides have potential applications in drug development, or additionally, as powerful tools in understanding normal/diseased states.
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•Green, iterative microwave synthesis of glycomimetic sialic acid oligosaccharides.•N-acylhydrazide inter-residue linkages are stable to cleavage.•Sialic acids are important carbohydrates in normal and disease states.•Stable glycomimetic sialic acid oligosaccharides have potential in pharmaceutical development.