Linkage-Editing Pseudo-Glycans: A Reductive α-Fluorovinyl--Glycosylation Strategy to Create Glycan Analogs with Altered Biological Activities.

The acetal (-glycoside) bonds of glycans and glycoconjugates are chemically and biologically vulnerable, and therefore -glycosides are of interest as more stable analogs. We hypothesized that, if the -glycoside linkage plays a vital role in glycan function, the biological activities of -glycoside analogs would vary depending on their substituents. Based on this idea, we adopted a "linkage-editing strategy" for the creation of glycan analogs (pseudo-glycans).