title: Formylbenzene diazonium hexafluorophosphate reagent for tyrosine-selective modification of proteins and the introduction of a bioorthogonal aldehyde.
abstract: 4-Formylbenzene diazonium hexafluorophosphate (FBDP) is a novel bench-stable crystalline diazonium salt that reacts selectively with tyrosine to install a bioorthogonal aldehyde functionality. Model studies with N-acyl-tyrosine methylamide allowed us to identify conditions optimal for tyrosine ligation reactions with small peptides and proteins. FBDP-based conjugation was used for the facile introduction of small molecule tags, poly(ethylene glycol) chains (PEGylation), and functional small molecules onto model proteins and to label the surface of living cells.
authors.affiliation: Departments of Chemistry and Molecular Biology, The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Rd., La Jolla, CA 92037, USA.
authors.forename: Julia
authors.initials: J
authors.lastname: Gavrilyuk
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Ban
authors.forename: Masanobu
authors.initials: M
authors.lastname: Nagano
authors.forename: Wataru
authors.initials: W
authors.lastname: Hakamata
authors.forename: Carlos F
authors.initials: CF
authors.lastname: Barbas
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000577:Amides / Q000737:chemistry; D000818:Animals; D019921:Biotinylation; D002417:Cattle; D003979:Diazonium Compounds / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents / Q000737:chemistry*; D008958:Models, Molecular; D009842:Oligopeptides / Q000032:analysis / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry*; D011506:Proteins / Q000032:analysis / Q000737:chemistry*; D013194:Staining and Labeling / Q000379:methods*; D014443:Tyrosine / Q000737:chemistry*
chemical_list: D000447:Aldehydes; D000577:Amides; D003979:Diazonium Compounds; D007202:Indicators and Reagents; D009842:Oligopeptides; D010710:Phosphates; D011506:Proteins; D014443:Tyrosine