Synthesis and galectin-binding activities of mercaptododecyl glycosides containing a terminal β-galactosyl group

Mercaptododecyl glycosides containing a terminal β-galactosyl group were prepared from d-galactose or from d-lactose via hexa-O-acetyl-lactal (10) as a key intermediate. Interactions of these glycolipids (5 kinds) and galectins (β-galactoside binding lectins, 6 species) were evaluated by surface plasmon resonance (SPR) method. High binding responses were observed for the lactoside, 2-deoxy-lactoside, and lactosaminide with some galectins (Gal-3, -4, -8), whereas the galactoside and 2,3-dideoxy-lactoside showed low binding activities.

Graphical abstractSynthesis of 12-mercaptododecyl β-galactoside-terminated glycosides and their galectin-binding activities evaluated by SPR measurements are described.Figure optionsDownload full-size imageDownload as PowerPoint slide