Stabilization of tandem dG-dA base pairs in DNA-hairpins: replacement of the canonical bases by 7-deaza-7-propynylpurines |
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Authors: | Seela Frank Budow Simone Shaikh Khalil I Jawalekar Anup M |
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Institution: | Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universit?t Osnabrück, Barbarastrasse 7, 49069 Osnabrück, Germany. Frank.Seela@uni-osnabrueck.de |
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Abstract: | The stabilizing effect of 7-propynylated 7-deazapurine nucleosides on DNA-hairpins and DNA-duplexes containing d(GA) mismatches was investigated. The corresponding oligonucleotides were synthesized using solid-phase synthesis. For this purpose, the phosphoramidite of 7-deaza-7-propynyl-2'-deoxyadenosine (3c) was prepared. The incorporation of 3c instead of dA into the tandem d(GA) base pair of a DNA-hairpin alters the secondary structure, but has a positive effect on the duplex stability. A complete replacement of the canonical nucleosides of the tandem d(GA) base pair by 3c and 7-deaza-7-propynyl-2'-deoxyguanosine results in a significant base pair stabilization. |
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