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| - 6-Aza-2‘-deoxyisocytidine: Synthesis, Properties ofOligonucleotides, and Base-Pair Stability Adjustment of DNA withParallel Strand Orientation
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| - 6-Aza-5-methyl-2‘-deoxyisocytidine (1a) and 6-aza-2‘-deoxyisocytidine (1b) have been synthesized,converted into phosphoramidite building blocks, and incorporated into oligodeoxynucleotides. Theglycosylic bond stability of 1a,b under acidic conditions increases compared to that of 5-methyl-2‘-deoxyisocytidine (2a) and 2‘-deoxyisocytidine (2b). Oligonucleotides incorporating 1a or 1b showan enhanced stability against the 3‘-exonuclease snake-venom phosphodiesterase. The duplexescontaining 6-azapyrimidine nucleosides 1a or 1b have lower Tm values than duplexes containing2a or 2b with either antiparallel or parallel chain orientation. This was used to adjust the stabilityof the tridentate m5iCd-dG base pair to the level of the bidentate reverse Watson−Crick dA-dTpair.
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