Stabilization of tandem dG-dA base pairs in DNA-hairpins: replacement of the canonical bases by 7-deaza-7-propynylpurines
Autor(en): | Seela, F Budow, S Shaikh, KI Jawalekar, AM |
Stichwörter: | Chemistry; Chemistry, Organic; DUPLEX DNA; FRAGMENTS; G.A MISMATCHES; NMR; OLIGONUCLEOTIDES; STABILITY; THERMODYNAMICS | Erscheinungsdatum: | 2005 | Herausgeber: | ROYAL SOC CHEMISTRY | Journal: | ORGANIC & BIOMOLECULAR CHEMISTRY | Volumen: | 3 | Ausgabe: | 23 | Startseite: | 4221 | Seitenende: | 4226 | Zusammenfassung: | 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. |
ISSN: | 14770520 | DOI: | 10.1039/b510444k |
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