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Tyrosine bioconjugation with hypervalent iodine.
Declas, Nina; Maynard, John R J; Menin, Laure; Gasilova, Natalia; Götze, Sebastian; Sprague, Jakob L; Stallforth, Pierre; Matile, Stefan; Waser, Jerome.
Afiliación
  • Declas N; Laboratory of Catalysis and Organic Synthesis, Institut des Sciences et Ingénierie Chimique, Ecole Polytechnique Fédérale de Lausanne CH-1015 Lausanne Switzerland jerome.waser@epfl.ch.
  • Maynard JRJ; Department of Organic Chemistry, University of Geneva 1211 Geneva Switzerland stefan.matile@unige.ch.
  • Menin L; Institut des Sciences et Ingénierie Chimique, Ecole Polytechnique Fédérale de Lausanne, EPFL 1015 Lausanne Switzerland.
  • Gasilova N; Institut des Sciences et Ingénierie Chimique, Ecole Polytechnique Fédérale de Lausanne, EPFL 1015 Lausanne Switzerland.
  • Götze S; Department of Paleobiotechnology, Leibniz Institute for Natural Product Research and Infection Biology, Hans Knöll Institute (HKI) 07745 Jena Germany.
  • Sprague JL; Department of Microbial Pathogenicity Mechanisms, Leibniz Institute for Natural Product Research and Infection Biology, Hans Knöll Institute (HKI) 07745 Jena Germany.
  • Stallforth P; Department of Paleobiotechnology, Leibniz Institute for Natural Product Research and Infection Biology, Hans Knöll Institute (HKI) 07745 Jena Germany.
  • Matile S; Department of Organic Chemistry, University of Geneva 1211 Geneva Switzerland stefan.matile@unige.ch.
  • Waser J; Laboratory of Catalysis and Organic Synthesis, Institut des Sciences et Ingénierie Chimique, Ecole Polytechnique Fédérale de Lausanne CH-1015 Lausanne Switzerland jerome.waser@epfl.ch.
Chem Sci ; 13(43): 12808-12817, 2022 Nov 09.
Article en En | MEDLINE | ID: mdl-36519034
Hypervalent iodine reagents have recently emerged as powerful tools for late-stage peptide and protein functionalization. Herein we report a tyrosine bioconjugation methodology for the introduction of hypervalent iodine onto biomolecules under physiological conditions. Tyrosine residues were engaged in a selective addition onto the alkynyl bond of ethynylbenziodoxolones (EBX), resulting in stable vinylbenziodoxolones (VBX) bioconjugates. The methodology was successfully applied to peptides and proteins and tolerated all other nucleophilic residues, with the exception of cysteine. The generated VBX were further functionalized by palladium-catalyzed cross-coupling and azide-alkyne cycloaddition reactions. The method could be successfully used to modify bioactive natural products and native streptavidin to enable thiol-mediated cellular uptake.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2022 Tipo del documento: Article Pais de publicación: Reino Unido
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Idioma: En Revista: Chem Sci Año: 2022 Tipo del documento: Article Pais de publicación: Reino Unido