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Ultrafast Au(III)-Mediated Arylation of Cysteine.

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Affiliations

  • 1. Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095, United States.
      Authors
    • Doud EA 1
    • Treacy JW 1
    • Chao EY 1
    • Montgomery HR 1
    • Kunkel GE 1
    • Olivares EJ 1
    • Adhami N 1
    • Kerr TA 1
    • Chen Y 1
    • Loo JA 1
    • Houk KN 1
    • Maynard HD 1
    • Spokoyny AM 1
    (13 authors)
  • 2. Department of Chemistry, University of Bath, Claverton Down, BA2 7AY Bath, U.K.
      Authors
    • Tilden JAR 2
    • Frost CG 2
    (2 authors)
  • 3. Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, California 92093, United States.
      Authors
    • Rheingold AL 3
    (1 author)

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Journal of the American Chemical Society, 24 Apr 2024, 146(18):12365-12374
https://doi.org/10.1021/jacs.3c12170 PMID: 38656163 

Free full text available after 08 May 2025

Abstract 

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.

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Read article at publisher's site: https://doi.org/10.1021/jacs.3c12170

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Funding 

Funders who supported this work.

California NanoSystems Institute

    Division of Chemistry (2)

    NIGMS NIH HHS (3)

    National Institute of General Medical Sciences (2)