Synthesis and Glycan-Protein Interaction Studies of Se -Sialosides by 77 Se NMR

Organic Letters
Tatsuya SuzukiHiromune Ando

Abstract

To expand the potential of Se-carbohydrates for multifunctional mimicry of sugars, herein we addressed the synthesis of the highly challenging and biologically significant Se-glycosides of sialic acid (Se-sialosides). An α-sialyl selenolate anion generated in situ smoothly reacted with electrophiles to give α-Se-sialosides as single stereoisomers. A Se-sialoside was sequentially incorporated with selenium, producing a triseleno-sialoside. This molecule was used as a 77Se NMR-active handle for studying glycan-protein interaction, revealing different binding profiles of sialic acid binding proteins.

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