Selecting one reagent from a mixture: Exploiting replication networks in dynamic covalent chemistry

ORGN 211

Douglas Philp, and Jan W Sadownik. School of Chemistry, University of St Andrews, North Haugh, St Andrews, KY16 9ST, United Kingdom
Dynamic covalent chemistry offers an opportunity to develop synthetic protocols that incorporate a degree of error checking through the dynamic and reversible association of the components of a target structure through covalent bonds. The limited number of organic reactions that form covalent bonds and that are also completely reversible under mild conditions hampers the development of this field. In addition, the ability of systems to select and amplify one species over all others in an equilibrating mixture is limited in approaches which consider only the thermodynamics of the system. We have developed a new dynamic exchange reaction and incorporated it within synthetic replicating systems. The coupling of dynamic exchange and replication creates systems capable of selecting and amplifying single molecular species from complex mixtures with selectivities of better than 15:1.

Molecular Recognition and Self-Assembly
8:30 AM-11:50 AM, Monday, August 18, 2008 Pennsylvania Convention Center -- 202 A/B, Oral

Division of Organic Chemistry

The 236th ACS National Meeting, Philadelphia, PA, August 17-21, 2008