Stabilization of tandem dG–dA base pairs in DNA-hairpins: replacement of the canonical bases by 7-deaza-7-propynylpurines
- 20 October 2005
- journal article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 3 (23) , 4221-4226
- https://doi.org/10.1039/b510444k
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.Keywords
This publication has 18 references indexed in Scilit:
- Oligonucleotides containing 7-propynyl-7-deazaguanine: synthesis and base pair stabilityTetrahedron, 2005
- Cleavage of fragments containing DNA mismatches by enzymic and chemical probesBiochemical Journal, 2003
- Propynyl groups in duplex DNA: stability of base pairs incorporating 7-substituted 8-aza-7-deazapurines or 5-substituted pyrimidinesNucleic Acids Research, 2002
- 7-Deazaadenine-DNA: Bulky 7-Iodo Substituents or Hydrophobic 7-Hexynyl Chains Are Well Accommodated in the Major Groove of Oligonucleotide DuplexesChemistry – A European Journal, 1998
- Stabilisation of duplex DNA by 7-halogenated 8-aza-7-deazaguaninesChemical Communications, 1998
- Palladium-Catalyzed Cross Coupling of 7-Iodo-2’-deoxytubercidin with Terminal AlkynesSynthesis, 1996
- The Thermal Stability of DNA Fragments With Tandem Mismatches at a d(CXYG)d(CY'X'G) SiteNucleic Acids Research, 1996
- Solution Structure of a GA Mismatch DNA Sequence, d(CCATGAATGG)2, Determined by 2D NMR and Structural Refinement MethodsBiochemistry, 1994
- Thermodynamics of DNA duplexes with adjacent G.cntdot.A mismatchesBiochemistry, 1991
- Kinetic basis of spontaneous mutationJournal of Molecular Biology, 1982