Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 42, Pages 10595-10600Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201802058
Keywords
alkynes; amides; cross coupling; gold catalysis; protein conjugation
Categories
Funding
- JSPS KAKENHI [JP16H03287, JP16K13104, JP15H05843]
- Russian Government Program of Competitive Growth of Kazan Federal University among World's Leading Academic Centers
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In previously reported work, Au-III complexes co-ordinated with 2-benzoylpyridine ligand, BPy-Au, were prebound to a protein and used to discover a novel protein-directed labeling approach with propargyl ester functional groups. In this work, further examination discovered that gold catalysts devoid of the 2-benzoylpyridine ligand (e.g., NaAuCl4) had significantly reduced levels of protein labeling. Mechanistic investigations then revealed that BPy-Au and propargyl esters undergo a rare example of C(sp(2))-C(sp) aryl-alkynyl cross-coupling, likely through spontaneous reductive elimination. Overall, these observations appear to suggest that BPy-Au-mediated, propargyl ester-based protein labeling acts via an activated ester intermediate, which contributes to our understanding of this process and will aid the expansion/optimization of gold-catalyst usage in future bioconjugation applications, especially in vivo.
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