2-Benzoylpyridine Ligand Complexation with Gold Critical for Propargyl Ester-Based Protein Labeling.
Chemistry
; 24(42): 10595-10600, 2018 Jul 25.
Article
em En
| MEDLINE
| ID: mdl-29791049
ABSTRACT
In previously reported work, AuIII complexes coordinated 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(sp2 )-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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01-internacional
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MEDLINE
Assunto principal:
Pargilina
/
Piridinas
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Ouro
Idioma:
En
Ano de publicação:
2018
Tipo de documento:
Article