Zwitterionic oligonucleotides: a study on binding properties of 2'-O-aminohexyl modifications |
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Authors: | Noe Christian R Winkler Johannes Urban Ernst Gilbert Matthias Haberhauer Georg Brunar Helmut |
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Affiliation: | Department für Medizinische/Pharmazeutische Chemie, Universit?t Wien, Pharmaziezentrum, Althanstrasse 14, Wien 1090, Austria. christian.noe@univie.ac.at |
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Abstract: | 2'-O-Aminohexyl side chains provide excellent conditions for zwitterionic interstrand and intrastrand interactions of oligonucleotides. 2'-O-Aminoalkylated phosphoramidites of adenosine and uridine were synthesized and incorporated in increasing number into homo adenosine and homo uridine/thymidine dodecamers, respectively. CD spectra of these dodecamers with complementary sense DNA exhibited a B-DNA type structure. While duplex stability values of all tested oligonucleotides were lower than those of the native oligonucleotides, they were significantly higher than those of 2'-O-heptyl modified oligonucleotides. The destabilization amounted to 0.9, 1.5, and 2.7 degrees C per modification for 2'-O-aminohexyl adenosine, 2'-O-aminohexyl uridine, and 2'-O-heptyl adenosine substitutions. These findings are pointing to a duplex stabilizing effect of the interaction of side chain amino groups with backbone phosphoric acid. |
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