C-Glycoside analogues of beta-galactosylceramide with a simple ceramide substitute: synthesis and binding to HIV-1 gp120

The synthesis and HIV-1 gp120 binding of C- and aza-C-glycoside analogues of beta-galactosylceramide (GalCer) that contain a simple C-17 hydrocarbon chain as a ceramide substitute are described. Both compounds originate from stearic acid, and a carbohydrate-derived thioacetal-alcohol, and their syntheses are potentially general for beta-C-galactosides and their aza-C-partners. They showed potent and specific affinity for gp120 in an assay based on the change of surface pressure when the glycolipid monolayers were exposed to solutions of gp120. Interestingly, the aza-C-glycoside exhibited a significantly higher affinity than GalCer, whereas the C-glycoside was as active as GalCer.