title: Arginine selective reagents for ligation to peptides and proteins.
abstract: A new class of arginine-specific bioconjugation reagents for protein labeling has been developed. This method utilizes a triazolyl-phenylglyoxal group on the probe molecule that reacts selectively with the guandinyl group of Arg residues in a protein or peptide. The reaction proceeds in neutral to basic bicarbonate buffers and is selective for arginine residues in peptides and folded proteins. Importantly, the triazolyl-phenylglyoxal group can be introduced into complex molecules containing alkyne groups using CuAAC chemistry, providing a robust approach for the generation of phenylglyoxal reactive groups into molecules to be covalently attached onto the surface of proteins. Copyright © 2016 European Peptide Society and John Wiley & Sons, Ltd.
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Rd., San Diego, CA, 92037, USA.
authors.forename: Darren A
authors.initials: DA
authors.lastname: Thompson
authors.affiliation: University of California, San Diego, 9500 Gilman Dr, San Diego, CA, 92093, USA.
authors.forename: Raymond
authors.initials: R
authors.lastname: Ng
authors.affiliation: Department of Chemistry, The Scripps Research Institute, 10550 N. Torrey Pines Rd., San Diego, CA, 92037, USA.
authors.forename: Philip E
authors.initials: PE
authors.lastname: Dawson
mesh_terms: D001120:Arginine / Q000378:metabolism*; D007202:Indicators and Reagents; D015335:Molecular Probes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D010658:Phenylglyoxal / Q000737:chemistry; D017510:Protein Folding; D011506:Proteins / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
chemical_list: D007202:Indicators and Reagents; D015335:Molecular Probes; D010455:Peptides; D011506:Proteins; D014230:Triazoles; D001120:Arginine; D010658:Phenylglyoxal
keywords: arginine; bioconjugation; chemical ligation; triazole