Terminal lipophilization of a unique DNA dodecamer by various nucleolipid headgroups: Their incorporation into artificial lipid bilayers and hydrodynamic properties

• Emma Werz and
• Helmut Rosemeyer

Beilstein J. Org. Chem. 2015, 11, 913–929, doi:10.3762/bjoc.11.103

• -2-oleoyl-sn-glycero-3-phosphoethanolamine (POPE), was studied by single molecule fluorescence spectroscopy and microscopy with the help of an optically transparent microfluidic sample carrier with perfusion capabilities. The incorporation of the lipo-oligonucleotides into the bilayer was studied

• lipo-oligonucleotides. Keywords: lipid bilayer; lipo-oligonucleotides; nucleic acids; nucleolipids; Introduction For proper cell function, the biosynthetic lipophilization of proteins and carbohydrates, such as palmitoylation and farnesylation, is of decisive importance [1]. The same seems to be true

• for bacterial tRNAs [2], which was postulated recently and substantiated by the finding of geranylated tRNAs. Therefore a continuously growing interest in so-called lipo-oligonucleotides (LONs) [3][4][5][6] can be observed. In a preceding manuscript [7] we described the base-specific DNA duplex

Specific DNA duplex formation at an artificial lipid bilayer: fluorescence microscopy after Sybr Green I staining

• Emma Werz and
• Helmut Rosemeyer

Beilstein J. Org. Chem. 2014, 10, 2307–2321, doi:10.3762/bjoc.10.240

• -biosynthetic lipophilization of various biomolecules such as of proteins and carbohydrates is of decisive importance for the correct function of the cell [1]. With the recent discovery of geranylated tRNAs in bacteria [2] the interest in so-called lipo-oligonucleotides (LONs) has grown tremendously [3][4]. The

• immobilization of lipo-oligonucleotides carrying a racemic bis(hexadecyloxy)propan-1-yl tag (1a) at the 5’-termini at an artificial lipid bilayer–water phase boundary. These were prepared using the cyanoethyl phosphoramidite 1b. A specific duplex formation with complementary cyanine-5 (Cy5)-labelled DNA strands

• , in order to see if this dye stains the complementary DNA strands 4 + 5, which are known to form a duplex at the bilayer membrane [19]. Firstly, we evaluated the optimal measuring conditions such as the volume, the Sybr Green I concentration as well as of the lipo-oligonucleotides. At this point we