Journal
CHEMICAL SCIENCE
Volume 9, Issue 8, Pages 2105-2112Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7sc04554a
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Funding
- National Science Foundation [CAREER 1554814]
- TriLink BioTechnologies
- Research Corporation Cottrell College Science Award
- Smith College
- McKinley Honors Fellowship
- Tomlinson funds
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1554814] Funding Source: National Science Foundation
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The challenge of site-selectivity must be overcome in many chemical research contexts, including selective functionalization in complex natural products and labeling of one biomolecule in a living system. Synthetic catalysts incorporating molecular recognition domains can mimic naturally-occurring enzymes to direct a chemical reaction to a particular instance of a functional group. We propose that DNA-conjugated small molecule catalysts (DCats), prepared by tethering a small molecule catalyst to a DNA aptamer, are a promising class of reagents for site-selective transformations. Specifically, a DNA-imidazole conjugate able to increase the rate of ester hydrolysis in a target ester by >100-fold compared with equimolar untethered imidazole was developed. Other esters are unaffected. Furthermore, DCat-catalyzed hydrolysis follows enzyme-like kinetics and a stimuli-responsive variant of the DCat enables programmable turn on of the desired reaction.
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