Reaction discovery enabled by DNA-templated synthesis and in vitro selection

Matthew W. Kanan, Mary M. Rozenman, Kaori Sakurai, Thomas M. Snyder and David R. Liu ()
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Matthew W. Kanan: Harvard University
Mary M. Rozenman: Harvard University
Kaori Sakurai: Harvard University
Thomas M. Snyder: Harvard University
David R. Liu: Harvard University

Nature, 2004, vol. 431, issue 7008, 545-549

Abstract: Abstract Current approaches to reaction discovery focus on one particular transformation. Typically, researchers choose substrates based on their predicted ability to serve as precursors for the target structure, then evaluate reaction conditions1,2,3,4,5,6 for their ability to effect product formation. This approach is ideal for addressing specific reactivity problems, but its focused nature might leave many areas of chemical reactivity unexplored. Here we report a reaction discovery approach that uses DNA-templated organic synthesis7,8,9,10 and in vitro selection to simultaneously evaluate many combinations of different substrates for bond-forming reactions in a single solution. Watson–Crick base pairing controls the effective molarities of substrates tethered to DNA strands; bond-forming substrate combinations are then revealed using in vitro selection for bond formation, PCR amplification and DNA microarray analysis. Using this approach, we discovered an efficient and mild carbon–carbon bond-forming reaction that generates an enone from an alkyne and alkene using an inorganic palladium catalyst. Although this approach is restricted to conditions and catalysts that are at least partially compatible with DNA, we expect that its versatility and efficiency will enable the discovery of additional reactions between a wide range of substrates.

Date: 2004
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DOI: 10.1038/nature02920

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