New tocopherol derivatives for functionalization of amino or carboxyl groups with lipid anchors

Abstract

Lipid anchors play an important biological role in natural proteins in particular in lipid membrane anchoring. This principle was extended to nonnatural nucleic acids, peptide nucleic acids (PNA) and peptides. In order to provide new lipophilic anchors for the introduction into peptide nucleic acids (PNA) or peptides, a number of new α-tocopherol derivatives were synthesized containing carboxylic acids, amino groups or alkyne groups as linking sites. Amongst them are compounds with one or with two tocopherol units. Sonogashira reaction turned out to be a useful tool in these approaches. The products were characterized by NMR-spectroscopy and MS. An unusual phenomenon was found in 2-propargylamino-4,6-difluorotriazine that exhibits two different chemical shifts in the 19 F-NMR spectrum for the two fluoro atoms.