title: Activity-Based Proteome Profiling Probes Based on Woodward's Reagent K with Distinct Target Selectivity.
abstract: Woodward's reagent K (WRK) is a reactive heterocyclic compound that has been employed in protein chemistry to covalently and unspecifically label proteins at nucleophilic amino acids, notably at histidine and cysteine. We have developed a panel of WRK-derived activity-based probes and show that surprisingly and unexpectedly, these probes are fairly selective for a few proteins in the human proteome. The WRK-derived probes show unique reactivity towards the catalytic N-terminal proline in the macrophage migration inhibitory factor (MIF) and can be used to label and, if equipped with a fluorophore, to image MIF activities in living cells.
authors.affiliation: Max Planck Institute of Molecular Physiology, Otto-Hahn-Strasse 11, Dortmund, Germany.
authors.forename: Yong
authors.initials: Y
authors.lastname: Qian
authors.affiliation: Max Planck Institute of Molecular Physiology, Otto-Hahn-Strasse 11, Dortmund, Germany.
authors.forename: Marc
authors.initials: M
authors.lastname: Schürmann
authors.affiliation: Max Planck Institute of Molecular Physiology, Otto-Hahn-Strasse 11, Dortmund, Germany.
authors.forename: Petra
authors.initials: P
authors.lastname: Janning
authors.affiliation: Department of Chemistry, Chemical Biology Centre (KBC), Umeå University, 90187, Umeå, Sweden. christian.hedberg@umu.se.
authors.forename: Christian
authors.initials: C
authors.lastname: Hedberg
authors.affiliation: Max Planck Institute of Molecular Physiology, Otto-Hahn-Strasse 11, Dortmund, Germany. herbert.waldmann@mpi-dortmund.mpg.de.|Technical University Dortmund, Department of Chemistry and Chemical Biology, Otto-Hahn-Strasse 6, Dortmund, Germany. herbert.waldmann@mpi-dortmund.mpg.de.
authors.forename: Herbert
authors.initials: H
authors.lastname: Waldmann
mesh_terms: D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D006367:HeLa Cells; D006801:Humans; D007555:Isoxazoles / Q000737:chemistry*; D008263:Macrophage Migration-Inhibitory Factors / Q000037:antagonists & inhibitors / Q000737:chemistry / Q000378:metabolism*; D008856:Microscopy, Fluorescence; D011392:Proline / Q000737:chemistry; D020543:Proteome / Q000032:analysis / Q000737:chemistry*; D034622:RNA Interference; D034741:RNA, Small Interfering / Q000378:metabolism; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D007555:Isoxazoles; D008263:Macrophage Migration-Inhibitory Factors; D020543:Proteome; D034741:RNA, Small Interfering; C009686:N-ethyl-5-phenylisoxazolium-3'-sulfonate; D011392:Proline
keywords: activity-based probes; fluorescent imaging; protein labeling; proteomics