A concise chemical synthesis of a fluorescent βGal-(1,4)-S-βGlc-Cer derivative and its enzymatic elongation by glycosyltransferases

A straightforward chemical synthesis of lyso-lactosylceramide with the terminal galactose linked to glucose through a β-S-glycosidic bond is reported. The product is labeled on the amino-group with tetramethylrhodamine enabling its ultrasensitive detection in capillary electrophoresis using laser-induced fluorescence. The fluorescent product disaccharide is resistant to hydrolysis by glycosidases but is shown to remain as an acceptor substrate for glycosyltransferases for the conversion into the trisaccharides GM3 and Gb3.