Parallel DNA containing pyrazolo[3,4-D]pyrimidine analogues of isoguanine.
The phosphoramidites of 8-aza-7-deaza-2'-deoxyisoguanosine (1a) and its bromo derivative 1b as well as of 6-aza-2'-deoxyisocytidine and its 5-methyl derivative (3a,b) were synthesized. Parallel-stranded duplexes containing the nucleosides 1a,b show a significantly enhanced duplex stability compared to those containing 2'-deoxyisoguanosine.
Seela
F
F
Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastr. 7, D-49076 Osnabrück, Germany.
Kröschel
R
R
He
Y
Y
D004247:DNA / Q000737:chemistry; D003849:Deoxyguanosine / Q000138:chemical synthesis / Q000737:chemistry*; D006147:Guanine / Q000031:analogs & derivatives* / Q000737:chemistry*; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry; D011720:Pyrazoles / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*
D009841:Oligonucleotides; D009943:Organophosphorus Compounds; D011720:Pyrazoles; D011743:Pyrimidines; C434331:phosphoramidite; D006147:Guanine; D004247:DNA; C008183:isoguanine; D003849:Deoxyguanosine