Structure of synthetic bis-sialyllactosyl-caldarchaeol (BSC), lactosyl-sialyllactosyl-caldarchaeol (LSC), and bis-lactosyl-caldarchaeol (BLC) derived from tritiated caldarchaeol (A). Asterisks denote position of tritium label. To check whether caldarchaeol derivatives are stretched across the lipid bilayer, BSC-containing liposomes were incubated with varying amounts of neuraminidase (B). Second lane from right shows LSC used here for reference and obtained as described in Materials and Methods. The right-most lane depicts neuraminidase treatment of BSC in TDC micelles. Following neuraminidase treatment as described in Materials and Methods, the products were separated by TLC and visualized and quantified by phosphoimaging. All assays were carried out in triplicate, and the results agreed within 5%. L, liposomal assay; M, micellar assay; R, reference.