Oligonucleotides containing pyrazolo[3,4-d]pyrimidines: 8-Aza-7-deazaadenines with bulky substituents in the 2- or 7-position.
The synthesis of the 2'-deoxyadenosine analogues 1b, 2b, and 3c modified at the 7- and/or 2-position is described. The effect of 7-chloro and 2-methylthio groups on the duplex stability is evaluated. For that, the nucleosides 1b, 2b, and 3c were converted to the corresponding phosphoramidites 15, 19, and 22, which were employed in the solid-phase oligonucleotide synthesis. In oligonucleotide duplexes, compound 1b forms stable base pairs with dT, of which the separated 1b-dT base pairs contribute stronger than that of the consecutive base pairs. Compound 2b shows universal base pairing properties while its N8 isomer 3c forms duplexes with lower stability.
Seela
Frank
F
Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universitdät Osnabrück, Osnabrück, Germany. frank.seela@uni-osnabrueck.de
Jawalekar
Anup M
AM
Sun
Lijuan
L
Leonard
Peter
P
D000225:Adenine / Q000031:analogs & derivatives / Q000737:chemistry*; D020029:Base Pairing; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D011720:Pyrazoles; D011743:Pyrimidines
D009838:Oligodeoxyribonucleotides; D011720:Pyrazoles; D011743:Pyrimidines; C014175:pyrazolo(3,4-d)pyrimidine; D000225:Adenine