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Exploring the Chemoselectivity towards Cysteine Arylation by Cyclometallated Au III Compounds: New Mechanistic Insights
Author(s) -
Thomas Sophie R.,
Bonsignore Riccardo,
Sánchez Escudero Jorge,
MeierMenches Samuel M.,
Brown Christopher M.,
Wolf Michael O.,
Barone Giampaolo,
Luk Louis Y. P.,
Casini Angela
Publication year - 2020
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.202000262
Subject(s) - chemoselectivity , chemistry , cysteine , electrospray ionization , mass spectrometry , density functional theory , computational chemistry , accelerator mass spectrometry , molecular mechanics , electrospray mass spectrometry , quantum chemical , combinatorial chemistry , high resolution , stereochemistry , molecule , electrospray , organic chemistry , catalysis , chromatography , molecular dynamics , enzyme , remote sensing , geology
To gain more insight into the factors controlling efficient cysteine arylation by cyclometallated 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 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.