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Exploring the Chemoselectivity towards Cysteine Arylation by Cyclometallated Au^III Compounds: New Mechanistic Insights.

ABSTRACT: 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.

SUBMITTER: Thomas SR

PROVIDER: S-EPMC7689846 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Exploring the Chemoselectivity towards Cysteine Arylation by Cyclometallated AuIII Compounds: New Mechanistic Insights.

Thomas Sophie R SR Bonsignore Riccardo R Sánchez Escudero Jorge J Meier-Menches Samuel M SM Brown Christopher M CM Wolf Michael O MO Barone Giampaolo G Luk Louis Y P LYP Casini Angela A

Chembiochem : a European journal of chemical biology 20200708 21

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 seco ...[more]

PMID: 32511840

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