title: Aqueous oxidative Heck reaction as a protein-labeling strategy.
abstract: An increasing number of chemical reactions are being employed for bio-orthogonal ligation of detection labels to protein-bound functional groups. Several of these strategies, however, are limited in their application to pure proteins and are ineffective in complex biological samples such as cell lysates. Here we present the palladium-catalyzed oxidative Heck reaction as a new and robust bio-orthogonal strategy for linking functionalized arylboronic acids to protein-bound alkenes in high yields and with excellent chemoselectivity even in the presence of complex protein mixtures from living cells. Advantageously, this reaction proceeds under aerobic conditions, whereas most other metal-catalyzed reactions require inert atmosphere.
authors.affiliation: Department of Pharmaceutical Gene Modulation, University of Groningen, Antonius Deusinglaan 1, 9713 AV Groningen (The Netherlands).
authors.forename: Maria Eleni
authors.initials: ME
authors.lastname: Ourailidou
authors.forename: Jan-Ytzen
authors.initials: JY
authors.lastname: van der Meer
authors.forename: Bert-Jan
authors.initials: BJ
authors.lastname: Baas
authors.forename: Margot
authors.initials: M
authors.lastname: Jeronimus-Stratingh
authors.forename: Aditya L
authors.initials: AL
authors.lastname: Gottumukkala
authors.forename: Gerrit J
authors.initials: GJ
authors.lastname: Poelarends
authors.forename: Adriaan J
authors.initials: AJ
authors.lastname: Minnaard
authors.forename: Frank J
authors.initials: FJ
authors.lastname: Dekker
mesh_terms: D000475:Alkenes / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry; D002384:Catalysis; D008958:Models, Molecular; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D011487:Protein Conformation; D011506:Proteins / Q000737:chemistry*; D013194:Staining and Labeling / Q000379:methods*; D013379:Substrate Specificity; D014867:Water / Q000737:chemistry*
chemical_list: D000475:Alkenes; D001897:Boronic Acids; D011506:Proteins; D014867:Water; D010165:Palladium
keywords: Heck reaction; cross-coupling; homogeneous catalysis; palladium; protein modifications