DNA-Catalyzed Introduction of Azide at Tyrosine for Peptide Modification

Puzhou Wang, Scott K Silverman

Research output: Contribution to journalArticle

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 - Jan 1 2016

Fingerprint

Catalytic DNA
Azides
Peptides
Tyrosine
DNA
Enzymes
Substrates
Anchors
Hydroxyl Radical
Functional groups
Polyethylene glycols
Amino acids
Labels
Amino Acids

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

DNA-Catalyzed Introduction of Azide at Tyrosine for Peptide Modification. / Wang, Puzhou; Silverman, Scott K.

In: Angewandte Chemie - International Edition, Vol. 55, No. 34, 01.01.2016, p. 10052-10056.

Research output: Contribution to journalArticle

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