6533b7d4fe1ef96bd1262a02
RESEARCH PRODUCT
Exploring the Chemoselectivity towards Cysteine Arylation by Cyclometallated Au III Compounds: New Mechanistic Insights
Samuel M. Meier-menchesSophie R. ThomasRiccardo BonsignoreAngela CasiniMichael O. WolfGiampaolo BaroneLouis Y. P. LukJorge Sánchez EscuderoChristopher M. Brownsubject
010405 organic chemistryChemistryElectrospray ionizationOrganic Chemistrycyclometallated gold complexes010402 general chemistryMass spectrometry01 natural sciencesBiochemistryCombinatorial chemistryMolecular mechanicsReductive elimination0104 chemical sciencesddc:cysteine arylationGold CompoundschemoselectivitySettore CHIM/03 - Chimica Generale E InorganicapeptidesMolecular MedicineDensity functional theoryChemoselectivityMolecular BiologyCysteinemass spectrometrydescription
To gain more insight into the factors controlling the efficient cysteine arylation by cyclometalated Au(III) 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 deducted 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2020-01-01 |