Synthesis of Functionalized Lipids, and Their Use for a Tunable Hydrophobization of Nucleosides and Nucleic Acids

Abstract

Two series of functionalized single and double side-chained lipid molecules (Schemes 1 and 2) were prepared. The compounds carry either terminal COOH, OH, or halogen substituents. Moreover, the double side-chained lipid 18 carries an internal alkyne functionality. The latter compound was used to hydrophobize thymidine at N(3) by base-catalyzed alkylation. Additionally, fully protected thymidine, 32, was N(3)-alkylated with the double side-chained alcohol 9 applying Mitsunobu reaction conditions.