Novel nucleic acid architectures involving locked nucleic acid (LNA) and pyrene residues: Results from an Indo-Danish collaboration*
B. Ravindra Babu1, Raunak1,2, Mads D. Sørensen3, Patrick J. Hrdlicka1, Smriti Trikha1,2, Ashok K. Prasad2, Virinder S. Parmar2, and Jesper Wengel1,‡
1Nucleic Acid Center, Department of Chemistry, University of Southern Denmark, Campusvej 55, DK-5230 Odense M, Denmark; 2Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India; 3Department of Chemistry, University of Copenhagen, DK-2100 Copenhagen, Denmark
Abstract: We report herein our results for locked nucleic acid (LNA)-type oligonucleotides containing pyrene residues. Pyrene has a large hydrophobic and planar surface area and is therefore a potential intercalating unit; furthermore, it is interesting as a fluorescent tag when covalently bound to DNA. Synthesis and hybridization of conformationally locked universal base surrogates are described together with efficient interstrand communication as shown by the formation of pyrene excimer bands for duplexes containing 2'-N-(pyren-1-yl)methyl-2'-amino-LNA monomers positioned in a zipper-like manner within a DNA duplex.
*Paper based on a presentation at the 24th International Symposium on the Chemistry of Natural Products and the 4th International Congress on Biodiversity, held jointly in Delhi, India, 26-31 January 2004. Other presentations are published in this issue, pp. 1-344.