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

ASJC Scopus subject areas

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

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    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