2′‐Linking of Lipids and Other Functions to Uridine through 1,2,3‐Triazoles and Membrane Anchoring of the Amphiphilic Products

Abstract

Abstract A straightforward synthesis of 2′‐functionalized uridines was developed based on a Cu‐catalyzed cycloaddition of 2′‐azido‐2′‐deoxyuridine and functionalized alkynes. The functions comprise biochemically important groups such as lipids, a fluorescent marker (Cy5 analogue), pentaacetylglucose, lysine and biotin, and are linked to the 2′‐position of uridine by a 1,2,3‐triazole ring. A number of NMR spectroscopic investigations revealed that the lipidated 2′‐triazolyl‐2′‐deoxyuridines anchor themselves in the phospholipid membranes without affecting the molecular order in the double layers; the polar moieties – uracil, ribose and triazole – are located in the lipid/water interface of the membrane.