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Scientific article
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English

Tyrosine bioconjugation with hypervalent iodine

Published inChemical science, vol. 13, no. 43, p. 12808-12817
Publication date2022-11-21
First online date2022-10-12
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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Citation (ISO format)
DECLAS, Nina et al. Tyrosine bioconjugation with hypervalent iodine. In: Chemical science, 2022, vol. 13, n° 43, p. 12808–12817. doi: 10.1039/d2sc04558c
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ISSN of the journal2041-6520
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Technical informations

Creation11/10/2022 8:49:00 AM
First validation11/10/2022 8:49:00 AM
Update time03/16/2023 8:54:06 AM
Status update03/16/2023 8:54:05 AM
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