Development of a fluorescent probe for the study of the sponge-derived simplexide immunological properties

Simplexide is a glycolipid of marine origin, endowed with immunological properties, composed of a long chain secondary alcohol glycosylated by an α-d-glucosyl-(1→4)-β-d-galactosyl disaccharide residue. Herein we describe the preparation of a fluorescent derivative of simplexide, labeled at position 6 of the distal glucose with a dansyl group, as a probe for future studies on the mechanism by which simplexide affects the immune system. Fluorescent simplexide was prepared from a 6″-amino functionalized compound, which in turn was obtained through a highly efficient glycosylation between the preformed activated disaccharide and the long chain secondary alcohol 18-pentatriacontanol.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Marine active compounds. ► Synthesis of a fluorescent glycolipid. ► Stereoselective glycosylation with a long-chain secondary alcohol.