Synthesis, molecular modeling studies and properties of oligonucleotides containing 5-(1H-1,2,3-triazol-4-yl)-2'-deoxyuridine derivatives

CARB 62

Petr Kocalka, Nicolai Krog Andersen, nka@ifk.sdu.dk, and Poul Nielsen, pon@ifk.sdu.dk. Department of Physics and Chemistry, University of Southern Denmark, Campusvej 55, Odense, 5230, Denmark
A series of 5-(1H-1,2,3-triazol-4-yl)-2'-deoxyuridine derivatives (X, Y, Z) has been synthesized and incorporated into oligonucleotides. These modifications show increasing thermal stability towards complementary DNA and RNA strands upon multiple incorporations of up to +5.1 °C per. modification relative to the unmodified duplexes. Decreases in thermal stability is observed with single incorporation of the monomers with up to −5.1 °C per. modification relative to the unmodified duplex. Molecular modelling indicates that the high difference in thermal stability is due to extended π-π stacking offered by the triazole moieties (monomer X) as well as the added aromatic moieties in case of monomers Y and Z. The monomers X, Y and Z were evaluated for their biophysical properties in terms of thermal stability, circular dichroism (duplex type) and pKa-values.

 

General Posters
6:00 PM-8:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Carbohydrate Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007