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Title: A DNA-conjugated small molecule catalyst enzyme mimic for site-selective ester hydrolysis
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.  more » « less
Award ID(s):
1554814
PAR ID:
10430677
Author(s) / Creator(s):
; ; ; ; ; ; ; ;
Date Published:
Journal Name:
Chemical Science
Volume:
9
Issue:
8
ISSN:
2041-6520
Page Range / eLocation ID:
2105 to 2112
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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