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  • Title: Oligonucleotide charge reversal: 2'-O-lysylaminohexyl modified oligonucleotides.
    Author: Winkler J, Noe CR.
    Journal: Nucleosides Nucleotides Nucleic Acids; 2007; 26(8-9):939-42. PubMed ID: 18058513.
    Abstract:
    A novel cationic building nucleoside building block designed for antisense and siRNA oligonucleotides is presented. Protected L-lysine was coupled to 2'-O-aminohexyluridine and the resulting nucleoside was phosphitylated for automated oligonucleotide synthesis. An increasing number of these 2'-O-lysylaminohexyl nucleosides lowered the melting temperature of desoxy-thymidine homododecamers, but the decrease was lower than that for DNA/RNA hybrids. Incubation with an exonuclease showed the exceptionally high resistance against enzymatic degradation. CD spectrometry revealed a gradual transition towards an A-type oligonucleotide structure. Based on these data, the cationic building block is particularly suited for gapmer antisense as well as siRNA oligonucleotides.
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