Convergent synthesis of structurally diverse mucin-like deoxyglycoside probes.

Abstract

The efficient synthesis of complex glycan ligands is essential to enable studies of glycan-protein recognition, as the study of glycan-mediated interactions unlocks our understanding of complex biological processes. The stereoselective synthesis of deoxy glycosides remains a significant challenge due to the absence of neighbouring-group participation and competing reaction pathways. In this work we report the convergent, stereoselective synthesis of eight structurally diverse carbohydrate ligands, incorporating 2-deoxy, 6-deoxy, N-acetyl and neuraminic acid motifs. Our synthetic strategy involves the use of a variety of common glycosyl acceptors and donors, allowing the convergent synthesis of each compound using robust synthetic methods. These azido-linked glycans provide a versatile platform for bioconjugation and will allow future studies into their roles in glycan-mediated interactions.

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