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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