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Tyrosine bioconjugation with hypervalent iodine.

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.

SUBMITTER: Declas N

PROVIDER: S-EPMC9645396 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

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Tyrosine bioconjugation with hypervalent iodine.

Declas Nina N Maynard John R J JRJ Menin Laure L Gasilova Natalia N Götze Sebastian S Sprague Jakob L JL Stallforth Pierre P Matile Stefan S Waser Jerome J

Chemical science 20221012 43

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 p ...[more]

PMID: 36519034

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