Synthesis of Nucleosides with 2′‐Fixed Lipid Anchors and Their Behavior in Phospholipid Membranes

Abstract

Abstract Various new nucleosides bearing one or two lipophilic groups at the 2′‐position have been synthesized. The lipophilic substituents were attached to a 2′‐hydroxy, 2′‐amino, or 2′‐thio function. These lipophilic nucleosides anchor in large unilamellar POPC vesicles serving as phospholipid membrane models. The insertion of these molecules into the membranes was investigated by NMR techniques. For comparison, nucleosides with two or three lipophilic groups at the 2′‐, 3′‐, or 5′‐positions have also been studied.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)