title: DNA-Catalyzed Introduction of Azide at Tyrosine for Peptide Modification.
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.
authors.affiliation: Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL, 61801, USA.
authors.forename: Puzhou
authors.identifier: 0000-0001-6636-4892
authors.initials: P
authors.lastname: Wang
authors.affiliation: Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, IL, 61801, USA. sks@illinois.edu.
authors.forename: Scott K
authors.identifier: 0000-0001-8166-3460
authors.initials: SK
authors.lastname: Silverman
mesh_terms: D001386:Azides / Q000737:chemistry / Q000378:metabolism*; D055162:Biocatalysis; D021881:DNA, Catalytic / Q000737:chemistry / Q000378:metabolism*; D008968:Molecular Conformation; D010455:Peptides / Q000737:chemistry / Q000378:metabolism*; D014443:Tyrosine / Q000737:chemistry / Q000378:metabolism*
chemical_list: D001386:Azides; D021881:DNA, Catalytic; D010455:Peptides; D014443:Tyrosine
keywords: DNA; deoxyribozymes; in vitro selection; peptide modification; peptides