title: 2-aza-2'-deoxyadenosine: synthesis, base-pairing selectivity, and stacking properties of oligonucleotides.
abstract: 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.
authors.affiliation: Laboratorium für Organische und Bioorganische Chemie Institut für Chemie, Fachbereich Biologie/Chemie, Universität Osnabrück, Germany.
authors.forename: T
authors.initials: T
authors.lastname: Sugiyama
authors.forename: E
authors.initials: E
authors.lastname: Schweinberger
authors.forename: Z
authors.initials: Z
authors.lastname: Kazimierczuk
authors.forename: N
authors.initials: N
authors.lastname: Ramzaeva
authors.forename: H
authors.initials: H
authors.lastname: Rosemeyer
authors.forename: F
authors.initials: F
authors.lastname: Seela
mesh_terms: 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
chemical_list: C113508:2-azido-2'-deoxyinosine; D001386:Azides; D009841:Oligonucleotides; C045138:2-azaadenosine; D007288:Inosine; D000241:Adenosine