Exploring the Chemoselectivity towards Cysteine Arylation by Cyclometallated AuIII Compounds: New Mechanistic Insights.
Sophie R ThomasRiccardo BonsignoreJorge Sánchez EscuderoSamuel M Meier-MenchesChristopher M BrownMichael O WolfGiampaolo BaroneLouis Y P LukAngela CasiniPublished in: Chembiochem : a European journal of chemical biology (2020)
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.
Keyphrases
- density functional theory
- mass spectrometry
- liquid chromatography
- molecular dynamics
- high resolution
- high resolution mass spectrometry
- tandem mass spectrometry
- simultaneous determination
- high performance liquid chromatography
- ms ms
- gas chromatography
- fluorescent probe
- capillary electrophoresis
- living cells
- solid phase extraction
- atomic force microscopy
- single molecule
- amino acid