ORGN 32 |
| Small-molecule DNA hybrids (SMDHs) comprised of an organic core surrounded by single stranded DNAs can be constructed in a modular fashion using three different strategies: traditional phosphoramidite synthesis, amide formation, and [azide + acetylene] “click” chemistry. Using Sonogashira coupling, halogenated molecular cores with varying geometries can be readily coupled to versatile acetylene-based small-molecule linkers possessing the appropriate functionalities for subsequent functionalization with DNA. The linker modules have been synthesized with alcohol, acetylene, and carboxylic acid terminal groups, which will react selectively with phosphoramidite-, azide-, and amide-functionalized DNA to form SMDHs with phosphate, triazole, and amide linkages, respectively (Figure). The modular feature of this approach allows for the facile tuning of the number of DNA strands around a rigid core as well as the angles between neighboring DNA strands. The well-defined geometry of the resulting hybrids makes possible a systematic evaluation of the parameters that govern the cooperative melting properties in DNA-hybrids. Such knowledge can then be used in the construction of new materials for diagnostics and molecular-switch applications.
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Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Sunday, August 19, 2007 BCEC -- 254 A/B, Oral
Division of Organic Chemistry |
