Ultrafast Au(III)-Mediated Arylation of Cysteine.
Evan A DoudJames A R TildenJoseph W TreacyElaine Y ChaoHayden R MontgomeryGrace E KunkelEileen J OlivaresNima AdhamiTyler A KerrYu ChenArnold L RheingoldJoseph A LooChristopher G FrostKendall N HoukHeather D MaynardAlexander M SpokoynyPublished in: Journal of the American Chemical Society (2024)
Through mechanistic work and rational design, we have developed the fastest organometallic abiotic Cys bioconjugation. As a result, the developed organometallic Au(III) bioconjugation reagents enable selective labeling of Cys moieties down to picomolar concentrations and allow for the rapid construction of complex heterostructures from peptides, proteins, and oligonucleotides. This work showcases how organometallic chemistry can be interfaced with biomolecules and lead to a range of reactivities that are largely unmatched by classical organic chemistry tools.