Synthesis of a Fluorescent Sulfatide for the Study of CD1 Antigen Binding Properties

A fluorescent derivative of sulfatide, labeled with a dansyl probe at position 6 of galactose, was prepared through a glycosylation reaction between a 6-O-functionalized galactose donor and 3-O-benzoyl-azidosphingosine. The sphingoid acceptor was obtained in high yield through exploitation of a highly stereoselective nucleophilic addition of pentadecyne to 2,3-O-cyclohexylidene-D-glyceraldehyde. The fluorescent sulfatide binds to soluble recombinant human CD1a and is a valuable tool for the study of CD1 antigen binding properties. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)