Site-Selective Functionalization of Methionine Residues via Photoredox Catalysis

Junyong Kim, Beryl X. Li, Richard Y.C. Huang, Jennifer X. Qiao, William R. Ewing, David W.C. Macmillan

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Bioconjugation technologies have revolutionized the practice of biology and medicine by allowing access to novel biomolecular scaffolds. New methods for residue-selective bioconjugation are highly sought to expand the toolbox for a variety of bioconjugation applications. Herein we report a site-selective methionine bioconjugation protocol that uses photoexcited lumiflavin to generate open-shell intermediates. This reduction-potential-gated strategy enables access to residues unavailable with traditional nucleophilicity-based conjugation methods. To demonstrate the versatility and robustness of this new protocol, we have modified various proteins and further utilized this functional handle to append diverse biological payloads.

Original languageEnglish (US)
Pages (from-to)21260-21266
Number of pages7
JournalJournal of the American Chemical Society
Volume142
Issue number51
DOIs
StatePublished - Dec 23 2020

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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