2-aza-2 `-deoxyadenosine: Synthesis, base-pairing selectivity, and stacking properties of oligonucleotides

Autor(en): Sugiyama, T
Schweinberger, E
Kazimierczuk, Z
Ramzaeva, N
Rosemeyer, H 
Seela, F
Stichwörter: 2-aza-2 `-deoxyadenosine; 2-AZAPURINES; Chemistry; Chemistry, Multidisciplinary; DERIVATIVES; DNA; DNA structures; duplex stability; GLYCOSYLATION; IMIDAZOLE NUCLEOSIDES; MOLECULES; NMR; nucleosides; oligonucleosides; RECOGNITION; RNA; STABILITY
Erscheinungsdatum: 2000
Herausgeber: WILEY-V C H VERLAG GMBH
Journal: CHEMISTRY-A EUROPEAN JOURNAL
Volumen: 6
Ausgabe: 2
Startseite: 369
Seitenende: 378
Zusammenfassung: 
2-Aza-2'-deoxyadenosine (2, z(2)A(d)) is synthesized via its 1,N-6-etheno derivative 7 and enzymatically deaminated to 2-aza-2'-deoxyinosine (3). Compound 2 is converted into the phosphoramidite building block 10b. This is employed in solid-phase oligonucleotide synthesis. The 2-azapurine base forms a strong base pair with guanine, but a much weaker one with adenine, thymine, and cytosine. Oligonucleotide duplexes with dangling nucleotide residues, such as 2-aza-2'-deoxyadenosine and 7-deaza-2'-deoxyadenosine (4, c(7)A(d)), either on one or both termini, are synthesized, and the thermal stability of the duplexes is correlated with the hydrophobic properties of the dangling nucleotide residues.
ISSN: 09476539
DOI: 10.1002/(SICI)1521-3765(20000117)6:2<369::AID-CHEM369>3.3.CO;2-U

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