DNA-Catalyzed Amide Hydrolysis

Cong Zhou, Joshua L. Avins, Paul C. Klauser, Benjamin M. Brandsen, Yujeong Lee, Scott K Silverman

Research output: Contribution to journalArticle

Abstract

DNA catalysts (deoxyribozymes) for a variety of reactions have been identified by in vitro selection. However, for certain reactions this identification has not been achieved. One important example is DNA-catalyzed amide hydrolysis, for which a previous selection experiment instead led to DNA-catalyzed DNA phosphodiester hydrolysis. Subsequent efforts in which the selection strategy deliberately avoided phosphodiester hydrolysis led to DNA-catalyzed ester and aromatic amide hydrolysis, but aliphatic amide hydrolysis has been elusive. In the present study, we show that including modified nucleotides that bear protein-like functional groups (any one of primary amino, carboxyl, or primary hydroxyl) enables identification of amide-hydrolyzing deoxyribozymes. In one case, the same deoxyribozyme sequence without the modifications still retains substantial catalytic activity. Overall, these findings establish the utility of introducing protein-like functional groups into deoxyribozymes for identifying new catalytic function. The results also suggest the longer-term feasibility of deoxyribozymes as artificial proteases.

Original languageEnglish (US)
Pages (from-to)2106-2109
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number7
DOIs
StatePublished - Mar 2 2016

Fingerprint

Catalytic DNA
Amides
hydrolysis
Hydrolysis
DNA
Functional groups
functional group
Proteins
protein
Nucleotides
Hydroxyl Radical
ester
Catalyst activity
Esters
Peptide Hydrolases
catalyst
Catalysts
experiment
Experiments

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Zhou, C., Avins, J. L., Klauser, P. C., Brandsen, B. M., Lee, Y., & Silverman, S. K. (2016). DNA-Catalyzed Amide Hydrolysis. Journal of the American Chemical Society, 138(7), 2106-2109. https://doi.org/10.1021/jacs.5b12647

DNA-Catalyzed Amide Hydrolysis. / Zhou, Cong; Avins, Joshua L.; Klauser, Paul C.; Brandsen, Benjamin M.; Lee, Yujeong; Silverman, Scott K.

In: Journal of the American Chemical Society, Vol. 138, No. 7, 02.03.2016, p. 2106-2109.

Research output: Contribution to journalArticle

Zhou, C, Avins, JL, Klauser, PC, Brandsen, BM, Lee, Y & Silverman, SK 2016, 'DNA-Catalyzed Amide Hydrolysis', Journal of the American Chemical Society, vol. 138, no. 7, pp. 2106-2109. https://doi.org/10.1021/jacs.5b12647
Zhou C, Avins JL, Klauser PC, Brandsen BM, Lee Y, Silverman SK. DNA-Catalyzed Amide Hydrolysis. Journal of the American Chemical Society. 2016 Mar 2;138(7):2106-2109. https://doi.org/10.1021/jacs.5b12647
Zhou, Cong ; Avins, Joshua L. ; Klauser, Paul C. ; Brandsen, Benjamin M. ; Lee, Yujeong ; Silverman, Scott K. / DNA-Catalyzed Amide Hydrolysis. In: Journal of the American Chemical Society. 2016 ; Vol. 138, No. 7. pp. 2106-2109.
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