2-aza-2'-deoxyadenosine: synthesis, base-pairing selectivity, and stacking properties of oligonucleotides.
2-Aza-2'-deoxyadenosine (2, z2Ad) is synthesized via its 1,N6-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, c7Ad), 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.
Sugiyama
T
T
Laboratorium für Organische und Bioorganische Chemie Institut für Chemie, Fachbereich Biologie/Chemie, Universität Osnabrück, Germany.
Schweinberger
E
E
Kazimierczuk
Z
Z
Ramzaeva
N
N
Rosemeyer
H
H
Seela
F
F
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D020029:Base Pairing; D001483:Base Sequence; D007288:Inosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D009690:Nucleic Acid Conformation; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry; D013816:Thermodynamics
C113508:2-azido-2'-deoxyinosine; D001386:Azides; D009841:Oligonucleotides; C045138:2-azaadenosine; D007288:Inosine; D000241:Adenosine