6-Aza-2 `-deoxyisocytidine: Synthesis, properties of oligonucleotides, and base-pair stability adjustment of DNA with parallel strand orientation

Autor(en): Seela, F
He, Y
Stichwörter: 2'-DEOXYISOGUANOSINE; Chemistry; Chemistry, Organic; ENZYMATIC INCORPORATION; ISOCYTIDINE; ISOGUANINE; ISOGUANOSINE; NUCLEOSIDES; OLIGODEOXYNUCLEOTIDES; PHOSPHORAMIDITE; RNA DUPLEXES; SPECTROSCOPY
Erscheinungsdatum: 2003
Herausgeber: AMER CHEMICAL SOC
Journal: JOURNAL OF ORGANIC CHEMISTRY
Volumen: 68
Ausgabe: 2
Startseite: 367
Seitenende: 377
Zusammenfassung: 
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. The glycosylic 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 show an enhanced stability against the T-exonuclease snake-venom phosphodiesterase. The duplexes containing 6-azapyrimidine nucleosides 1a or 1b have lower T-m values than duplexes containing 2a or 2b with either antiparallel or parallel chain orientation. This was used to adjust the stability of the tridentate m(5)iC(d)-dG base pair to the level of the bidentate reverse Watson-Crick dA-dT pair.
ISSN: 00223263
DOI: 10.1021/jo020507n

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