Synthesis and transmembrane transport studies by NMR of a glucosyl phospholipid of thymidine

A phosphotriester derivative of thymidine, glucose, and hexadecanol was prepared by the nucleophilic displacement of 1-bromohexadecane by 6-glucopyranosyl 5'-thymidinyl phosphate. This compound was synthesized as a model of a transport molecule related to dolichyl 1-glucose phosphate. Its structure and interaction with large unilamellar vesicles were studied by super(1)H, super(13)C, and super(31)P NMR spectroscopy: the detection of the phosphotriester of thymidine inside the vesicles implied its transfer across the lipid bilayer, in contrast with its phosphodiester precursors which either did not interact with the membrane or alter the lipid layer.