Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 14, Issue 22, Pages 6640-6645Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200800514
Keywords
excimers; fluorescence oligonucleotides; self-assembly; stacking interactions
Categories
Ask authors/readers for more resources
Perylene-3,4:9,10-tetracarboxylic acid bisimides (PBs) were incorporated synthetically into oligonucleotides by using automated DNA building-block chemistry. The 2'-deoxyribofuranoside of the natural nucleosides was replaced by (S)-aminopropan-2,3-diol as an acyclic linker between the phosphodiester bridges that is tethered to one of the imide nitrogen atoms of the PB dye. The S configuration of this linker was chosen to mimic the stereochemical situation at the 3'position of the natural 2'-deoxyribofur-anosides. By using this strategy, up to six PB dyes were incorporated in the middle of 18-mer DNA duplexes by using interstrand alternating sequences of PBs with thymines or an abasic site analogue. Both PB dimers and PB hexamers as artificial base substitutions inside the duplexes yield characteristic excimer-type fluorescence. The stacking properties of the PB chromophores are modulated by the presence or absence of thymines opposite the PB modification site in the counterstrand. The interstrand PB dimers can be regarded as hydrophobically interacting base pairs, which display a characteristic fluorescence readout signal. Hence, for the PB hexamers, we proposed a zipperlike recognition motif that is formed inside duplex DNA. The PB zipper shows characteristic excimer-type emission as a fluorescence readout signal for the pairing interaction.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available