Tyrosine bioconjugation with hypervalent iodine (original) (raw)
* Corresponding authors
a Laboratory of Catalysis and Organic Synthesis, Institut des Sciences et Ingénierie Chimique, Ecole Polytechnique Fédérale de Lausanne, Lausanne, Switzerland
E-mail: jerome.waser@epfl.ch
b Department of Organic Chemistry, University of Geneva, 1211 Geneva, Switzerland
E-mail: stefan.matile@unige.ch
c Institut des Sciences et Ingénierie Chimique, Ecole Polytechnique Fédérale de Lausanne, EPFL, 1015 Lausanne, Switzerland
d Department of Paleobiotechnology, Leibniz Institute for Natural Product Research and Infection Biology, Hans Knöll Institute (HKI), 07745 Jena, Germany
e Department of Microbial Pathogenicity Mechanisms, Leibniz Institute for Natural Product Research and Infection Biology, Hans Knöll Institute (HKI), 07745 Jena, Germany
Abstract
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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DOI
https://doi.org/10.1039/D2SC04558C
Article type
Edge Article
Submitted
15 Aug 2022
Accepted
03 Oct 2022
First published
12 Oct 2022
This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry
Download Citation
Chem. Sci., 2022,13, 12808-12817
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Tyrosine bioconjugation with hypervalent iodine
N. Declas, J. R. J. Maynard, L. Menin, N. Gasilova, S. Götze, J. L. Sprague, P. Stallforth, S. Matile and J. Waser,Chem. Sci., 2022, 13, 12808DOI: 10.1039/D2SC04558C
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