DNAzyme-Catalyzed Site-Specific N-Acylation of DNA Oligonucleotide Nucleobases

Morgan M. Kennebeck, Caroline K. Kaminsky, Maria A. Massa, Prakriti K. Das, Robert D. Boyd, Michelle Bishka, J. Tomas Tricarico, Scott K. Silverman

Research output: Contribution to journalArticlepeer-review


We used in vitro selection to identify DNAzymes that acylate the exocyclic nucleobase amines of cytidine, guanosine, and adenosine in DNA oligonucleotides. The acyl donor was the 2,3,5,6-tetrafluorophenyl ester (TFPE) of a 5′-carboxyl oligonucleotide. Yields are as high as >95 % in 6 h. Several of the N-acylation DNAzymes are catalytically active with RNA rather than DNA oligonucleotide substrates, and eight of nine DNAzymes for modifying C are site-specific (>95 %) for one particular substrate nucleotide. These findings expand the catalytic ability of DNA to include site-specific N-acylation of oligonucleotide nucleobases. Future efforts will investigate the DNA and RNA substrate sequence generality of DNAzymes for oligonucleotide nucleobase N-acylation, toward a universal approach for site-specific oligonucleotide modification.

Original languageEnglish (US)
Article numbere202317565
JournalAngewandte Chemie - International Edition
Issue number7
StatePublished - Feb 12 2024


  • Deoxyribozymes
  • in Vitro Selection
  • Nucleic Acids
  • Oligonucleotides
  • Ribozymes

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry


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