501334-99-2Relevant academic research and scientific papers
The effect of a non-nucleosidic phenanthrene building block on DNA duplex stability
Langenegger, Simon M.,Haener, Robert
, p. 3414 - 3421 (2002)
Oligonucleotides containing a phenanthrene-derived, non-nucleosidic building block with flexible linkers were synthesized. The effect of the phenanthrene moiety on duplex stability at different positions was investigated. Placement of two phenanthrene residues in opposite positions had a slightly positive effect on duplex stability. This positive effect was further increased, when two phenanthrene pairs were juxtaposed. In contrast, introduction of a single phenanthrene unit opposite to an adenosine or a thymidine led to a destabilization of the duplex. A model of a phenanthrene-modified duplex is proposed.
Phenanthrene-derived DNA hairpin mimics
Stutz, Alfred,Langenegger, Simon M.,Haener, Robert
, p. 3156 - 3163 (2007/10/03)
Self-complementary oligodeoxynucleotides containing 3,6-disubstituted phenanthrenes adopt highly stable, hairpin-like structures. The thermodynamic stability of the hairpin mimics depends on the overall length of the phenanthrene building block. Hairpin loops composed of a phenanthrene-3,6-dicarboxamide and ethylene linkers were found to be optimal. The hairpin mimics are more stable than the analogous hairpins containing either a dT4 or dA4 tetraloop. Model studies indicate that the thermodynamic stability of the hairpin mimics is primarily due to aromatic stacking of the phenanthrene-3,6-dicarboxamide onto the adjoining base pair of the DNA duplex.
