Pyrazolo[3,4-d]pyrimidine nucleic acids: adjustment of the dA-dT to the dG-dC base pair stability.
The pyrazolo[3,4-d]pyrimidine-4,6-diamine nucleosides 2b-d stabilize the dA-dT base pair significantly when the dA-residue is replaced. Oligonucleotide duplexes incorporating 2b-d show a 4-6 degrees C Tm increase per modification. The 7-bromo compound 2b harmonizes the stability of the dA-dT vs. the dG-dC pair. According to this the stability of such duplexes depends no longer on the base pair composition of a DNA molecule.
He
J
J
Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Osnabrück, Germany.
Becher
G
G
Budow
S
S
Seela
F
F
D020029:Base Pairing; D001483:Base Sequence; D002151:Calorimetry; D003839:Deoxyadenosines / Q000737:chemistry*; D003841:Deoxycytidine / Q000737:chemistry*; D003849:Deoxyguanosine / Q000737:chemistry*; D004355:Drug Stability; D009838:Oligodeoxyribonucleotides / Q000737:chemistry; D011720:Pyrazoles / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*; D013816:Thermodynamics; D013941:Thymine / Q000737:chemistry*
D003839:Deoxyadenosines; D009838:Oligodeoxyribonucleotides; D011720:Pyrazoles; D011743:Pyrimidines; D003841:Deoxycytidine; C014175:pyrazolo(3,4-d)pyrimidine; D003849:Deoxyguanosine; D013941:Thymine