Nucleosides and nucleotides. 153. Effects of 2'α- and 2'-β-bromo-2'- deoxyadenosine on oligonucleotide hybridization and nuclease stability

Article abstract of DOI:10.1016/S0960-894X(96)00277-6

1-(2-Bromo-2-deoxy-β-D-ribofuranosyl)adenine (1) and 1-(2-bromo-2- deoxy-β-D-arabinofuranosyl)adenine (2) were incorporated into DNA pentadecamers. The oligonucleotides containing 1 destabilized DNA/DNA and DNA/RNA duplex formation. However, the oligonucleotides containing 2 slightly stabilized DNA/DNA duplex formation, although they decreased the stability of DNA/RNA duplexes. Furthermore, the oligonucleotide containing 2 was more resistant to snake venom phosphodiesterase than an unmodified oligonucleotide (dA)₁₅ and the oligonucleotide containing 1.