Optoglycomics: Synthesis and Function of Photochromic Glycoconjugates

Abstract

Optoglycomics describes an emerging research field in which photoswitchable glycoconjugates are employed to probe and control carbohydrate–protein interactions with light. In most cases, azobenzene serves as the photoswitchable chromophore, which can be reversibly isomerized between its E and Z state, thereby substantially altering the spatial presentation of conjugated glycans. This light-induced conformational change can modulate the affinity of glycan ligands for their receptors and the inhibitory properties of glycosidase and glycosyltransferase inhibitors. Furthermore, glycosylated surfaces, including the cellular glycocalyx, as well as other glycosylated supramolecular assemblies, can be manipulated with the high spatial and temporal precision afforded by light. Although optoglycomics is still in its infancy, the remarkable success of photopharmacology suggests that it has the potential to become a powerful tool for investigating the still not conclusively understood complexity of glycobiology and to inspire new diagnostic and therapeutic strategies for glycan-associated diseases.