Small-molecule DNA hybrids (SMDH's): Syntheses and recognition properties

ORGN 764

Brian R. Stepp, b-stepp@northwestern.edu, Julianne Gibbs Davis, j-gibbs1@northwestern.edu, Dorothea Li Feng Koh, dotkoh@northwestern.edu, and SonBinh T. Nguyen, stn@northwestern.edu. Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, IL 60208-3113
A series of rigid small-molecules based on phenylacetylene motifs have been synthesized, and subsequently functionalized with oligonucleotide strands to form small-molecule DNA hybrids (SMDH's)(Figure). As models for elucidating the origin of sharp-melting in organic polymer materials, these SMDH's have been designed such that the number and orientation of oligonucleotides on an individual unit can be controlled and tuned. Aggregates are formed when an SMDH is exposed to its complementarily functionalized SMDH or a polymer-DNA hybrid possessing complementary DNA strands. The effect of the number of strands and their orientation on the thermal and recognition properties of these aggregates will be compared to that of free-DNA duplexes.