Base-modified oligonucleotides with increased duplex stability: pyrazolo[3,4-d] pyrimidines replacing purines.
Oligonucleotides incorporating 8-aza-7-dazapurines (pyrazolo[3,4-d]pyrimidines) were synthesized. The corresponding nucleosides were prepared and were converted into phosphoramidites. The oligonucleotide duplex stability was studied and was compared to that of the parent compounds containing the canonical purine nucleosides. The presence of 7-halogeno or 7-alkynyl substituents increases the duplex stability significantly.
Seela
Frank
F
Laboratorium für Organishe und Bioorganische Chemie, Institut für Chemie, Unversität Osnabrück, Germany.
He
Yang
Y
He
Junlin
J
Becher
Georg
G
Kröschel
Rita
R
Zulauf
Matthias
M
Leonard
Peter
P
D001483:Base Sequence; D002855:Chromatography, Thin Layer; D019906:Nuclear Magnetic Resonance, Biomolecular; D009841:Oligonucleotides / Q000737:chemistry*; D011687:Purines / Q000737:chemistry*; D011720:Pyrazoles / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*; D013816:Thermodynamics
D009841:Oligonucleotides; D011687:Purines; D011720:Pyrazoles; D011743:Pyrimidines; C014175:pyrazolo(3,4-d)pyrimidine