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Tyrosine bioconjugation with hypervalent iodine.

Nina Declas1, John R J Maynard2, Laure Menin3

  • 1Laboratory of Catalysis and Organic Synthesis, Institut des Sciences et Ingénierie Chimique, Ecole Polytechnique Fédérale de Lausanne CH-1015 Lausanne Switzerland jerome.waser@epfl.ch.

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|December 15, 2022
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Summary

We developed a new method for modifying peptides and proteins using hypervalent iodine reagents under physiological conditions. This tyrosine bioconjugation introduces stable vinylbenziodoxolones (VBX) for further functionalization and cellular uptake.

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Area of Science:

  • Biochemistry
  • Organic Chemistry
  • Chemical Biology

Background:

  • Hypervalent iodine reagents are increasingly used for late-stage functionalization of peptides and proteins.
  • Developing selective and efficient bioconjugation methods under physiological conditions is crucial for biological applications.

Purpose of the Study:

  • To establish a novel tyrosine bioconjugation methodology using hypervalent iodine.
  • To enable the introduction of hypervalent iodine onto biomolecules under physiological conditions.
  • To demonstrate the utility of the generated bioconjugates for further functionalization and biological applications.

Main Methods:

  • Selective addition of tyrosine residues to ethynylbenziodoxolones (EBX).
  • Formation of stable vinylbenziodoxolones (VBX) bioconjugates.
  • Subsequent functionalization of VBX via palladium-catalyzed cross-coupling and click chemistry (azide-alkyne cycloaddition).

Main Results:

  • Successful tyrosine bioconjugation methodology reported.
  • Stable VBX bioconjugates formed under physiological conditions.
  • Method tolerated most nucleophilic residues except cysteine.
  • VBX conjugates were effectively modified using cross-coupling and click chemistry.
  • Application to natural products and streptavidin enabled thiol-mediated cellular uptake.

Conclusions:

  • A versatile tyrosine bioconjugation method using hypervalent iodine reagents was developed.
  • The method allows for late-stage functionalization of peptides and proteins under mild conditions.
  • The generated VBX bioconjugates serve as versatile platforms for further chemical modifications and biological applications.