Exploring the Chemoselectivity towards Cysteine Arylation by Cyclometallated Au(III)Compounds: New Mechanistic Insights
- Author(s)
- Sophie R. Thomas, Riccardo Bonsignore, Jorge Sanchez Escudero, Samuel M. Meier-Menches, Christopher M. Brown, Michael O. Wolf, Giampaolo Barone, Louis Y. P. Luk, Angela Casini
- 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.
- Organisation(s)
- Department of Analytical Chemistry
- External organisation(s)
- Cardiff University, University of British Columbia (UBC), Università degli Studi di Palermo, Technische Universität München
- Journal
- ChemBioChem: a european journal of chemical biology
- Volume
- 21
- Pages
- 3071-3076
- No. of pages
- 6
- ISSN
- 1439-4227
- DOI
- https://doi.org/10.1002/cbic.202000262
- Publication date
- 07-2020
- Peer reviewed
- Yes
- Austrian Fields of Science 2012
- 106002 Biochemistry, 106023 Molecular biology, 301305 Medical chemistry
- Keywords
- ASJC Scopus subject areas
- Molecular Medicine, Molecular Biology, Biochemistry, Organic Chemistry
- Portal url
- https://ucrisportal.univie.ac.at/en/publications/959e3016-e6c2-4ab0-a34e-e8aaa5e9d34e