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A DNA-conjugated small molecule catalyst enzyme mimic for site-selective ester hydrolysis

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Abstract

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.

Graphical abstract: A DNA-conjugated small molecule catalyst enzyme mimic for site-selective ester hydrolysis

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Publication details

The article was received on 20 Oct 2017, accepted on 10 Jan 2018 and first published on 15 Jan 2018


Article type: Edge Article
DOI: 10.1039/C7SC04554A
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY license
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    A DNA-conjugated small molecule catalyst enzyme mimic for site-selective ester hydrolysis

    Moira L. Flanagan, A. E. Arguello, D. E. Colman, J. Kim, J. N. Krejci, S. Liu, Y. Yao, Y. Zhang and D. J. Gorin, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C7SC04554A

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