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Abstract
To gain more insight into the factors controlling efficient cysteine arylation by cyclometallated AuIII complexes, the reaction between selected gold compounds and different peptides was investigated by high‐resolution liquid chromatography electrospray ionization mass spectrometry (HR‐LC‐ESI‐MS). The deduced mechanisms of C−S cross‐coupling, also supported by density functional theory (DFT) and quantum mechanics/molecular mechanics (QM/MM) calculations, evidenced the key role of secondary peptidic gold binding sites in favouring the process of reductive elimination.
Highlights
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To gain more insight into the factors controlling efficient cysteine arylation by cyclometallated AuIII complexes, the reaction between selected gold compounds and different peptides was investigated by high-resolution liquid chromatography electrospray ionization mass spectrometry (HR-LC-ESIMS)
Some examples have appeared concerning the use of gold compounds for selective bioorthogonal transformations through C C or C X (X = heteroatom) bond formation for different applications in chemical biology.[1e]. Many of the investigations exploit the propensity of both AuIII and AuI ions to activate alkynes towards nucleophilic addition for catalysis
Summary
Exploring the Chemoselectivity towards Cysteine Arylation by Cyclometallated AuIII Compounds: New Mechanistic. Some examples have appeared concerning the use of gold compounds for selective bioorthogonal transformations through C C or C X (X = heteroatom) bond formation for different applications in chemical biology.[1e] Many of the investigations exploit the propensity of both AuIII and AuI ions to activate alkynes towards nucleophilic addition for catalysis. In this context, selective cysteine arylation using organogold reagents represents another important example of metalmediated bioconjugation reactions.
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