title: Selective irreversible chemical tagging of cysteine with 3-arylpropiolonitriles.
abstract: Exquisite chemoselectivity for cysteine has been found for a novel class of remarkably hydrolytically stable reagents, 3-arylpropiolonitriles (APN). The efficacy of the APN-mediated tagging was benchmarked against other cysteine-selective methodologies in a model study on a series of traceable amino acid derivatives. The selectivity of the methodology was further explored on peptide mixtures obtained by trypsin digestion of lysozyme. Additionally, the superior stability of APN-cysteine conjugates in aqueous media, human plasma, and living cells makes this new thiol-click reaction a promising methodology for applications in bioconjugation.
authors.affiliation: Laboratory of Functional Chemo-Systems and §Laboratory V-SAT (CAMB UMR 7199, CNRS), Labex Medalis, University of Strasbourg , 74 Route du Rhin, 67401 Illkirch-Graffenstaden, France.
authors.forename: Oleksandr
authors.initials: O
authors.lastname: Koniev
authors.forename: Geoffray
authors.initials: G
authors.lastname: Leriche
authors.forename: Marc
authors.initials: M
authors.lastname: Nothisen
authors.forename: Jean-Serge
authors.initials: JS
authors.lastname: Remy
authors.forename: Jean-Marc
authors.initials: JM
authors.lastname: Strub
authors.forename: Christine
authors.initials: C
authors.lastname: Schaeffer-Reiss
authors.forename: Alain
authors.initials: A
authors.lastname: Van Dorsselaer
authors.forename: Rachid
authors.initials: R
authors.lastname: Baati
authors.forename: Alain
authors.initials: A
authors.lastname: Wagner
mesh_terms: D000595:Amino Acid Sequence; D002853:Chromatography, Liquid; D003545:Cysteine / Q000737:chemistry*; D006801:Humans; D008956:Models, Chemical; D008969:Molecular Sequence Data; D009113:Muramidase / Q000737:chemistry; D009570:Nitriles / Q000737:chemistry*; D053719:Tandem Mass Spectrometry
chemical_list: D009570:Nitriles; D009113:Muramidase; D003545:Cysteine