DNA-Catalyzed Introduction of Azide at Tyrosine for Peptide Modification

Puzhou Wang, Scott K. Silverman

Research output: Contribution to journalArticlepeer-review

Abstract

We show that DNA enzymes (deoxyribozymes) can introduce azide functional groups at tyrosine residues in peptide substrates. Using in vitro selection, we identified deoxyribozymes that transfer the 2′-azido-2′-deoxyadenosine 5′-monophosphoryl group (2′-Az-dAMP) from the analogous 5′-triphosphate (2′-Az-dATP) onto the tyrosine hydroxyl group of a peptide, which is either tethered to a DNA anchor or free. Some of the new deoxyribozymes are general with regard to the amino acid residues surrounding the tyrosine, while other DNA enzymes are sequence-selective. We use one of the new deoxyribozymes to modify free peptide substrates by attaching PEG moieties and fluorescent labels.

Original languageEnglish (US)
Pages (from-to)10052-10056
Number of pages5
JournalAngewandte Chemie - International Edition
Volume55
Issue number34
DOIs
StatePublished - Aug 16 2016

Keywords

  • DNA
  • deoxyribozymes
  • in vitro selection
  • peptide modification
  • peptides

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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