A DNA-Conjugated Small Molecule Catalyst Enzyme Mimic for Site-Selective Ester Hydrolysis

Authors

Moira L. Flanagan, Smith College
A. Emilia Arguello, Smith College
Drew E. Colman, Smith College
Jiyeon Kim, Smith College
Jesse N. Krejci, Smith College
Shimu Liu, Smith College
Yueyu Yao, Smith College
Yu Zhang, Smith College
David J. Gorin, Smith CollegeFollow

Document Type

Article

Publication Date

1-10-2018

Publication Title

Chemical Science

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.

Issue

9

First Page

2105

Last Page

2112

DOI

10.1039/c7sc04554a

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

Comments

Archived as published.

Recommended Citation

Flanagan, Moira L.; Arguello, A. Emilia; Colman, Drew E.; Kim, Jiyeon; Krejci, Jesse N.; Liu, Shimu; Yao, Yueyu; Zhang, Yu; and Gorin, David J., "A DNA-Conjugated Small Molecule Catalyst Enzyme Mimic for Site-Selective Ester Hydrolysis" (2018). Chemistry: Faculty Publications, Smith College, Northampton, MA.
https://scholarworks.smith.edu/chm_facpubs/16