Synthesis, Conformational Studies, Binding Assessment and Liposome Insertion of a Thioether-Bridged Mimetic of the Antigen GM3 Ganglioside Lactone

We report the conformational analysis and synthesis of a spiro glycoside, a thioether-bridged mimetic of GM3 lactone, which is a conformational analogue of the parent lactone with a manno residue that replaces the sialic portion. The synthesis, we have developed capitalizes on an unconventional strategy to achieve the tricyclic spiro unit, and can feature any lactone-like gangliosidic derivative.