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

Sophie R. Thomas; Riccardo Bonsignore; Jorge Sánchez Escudero; Samuel M. Meier‐Menches; Christopher M. Brown; Michael O. Wolf; Giampaolo Barone; Louis Y. P. Luk; Angela Casini

doi:10.1002/cbic.202000262

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

Sophie R. Thomas
, Riccardo Bonsignore
, Jorge Sánchez Escudero
, Samuel M. Meier‐Menches
, Christopher M. Brown
, Michael O. Wolf
, Giampaolo Barone
, Louis Y. P. Luk
, Angela Casini

School of Chemistry, Pharmacy and Pharmacology

Research output: Contribution to journal › Article › peer-review

31 Citations (Scopus)

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.

Original language	English
Pages (from-to)	3071-3076
Number of pages	6
Journal	ChemBioChem
Volume	21
Issue number	21
Early online date	8 Jul 2020
DOIs	https://doi.org/10.1002/cbic.202000262
Publication status	Published - 2 Nov 2020

Keywords

chemoselectivity
cyclometallated gold complexes
cysteine arylation
mass spectrometry
peptides

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ChemBioChem - 2020 - Thomas - Exploring the Chemoselectivity towards Cysteine Arylation by Cyclometallated AuIII Compounds Final published version, 1.36 MBLicence: CC BY

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title = "Exploring the Chemoselectivity towards Cysteine Arylation by Cyclometallated AuIII 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.",

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doi = "10.1002/cbic.202000262",

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AU - Thomas, Sophie R.

AU - Bonsignore, Riccardo

AU - Escudero, Jorge Sánchez

AU - Meier‐Menches, Samuel M.

AU - Brown, Christopher M.

AU - Wolf, Michael O.

AU - Barone, Giampaolo

AU - Luk, Louis Y. P.

AU - Casini, Angela

PY - 2020/11/2

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N2 - 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.

AB - 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.

KW - chemoselectivity

KW - cyclometallated gold complexes

KW - cysteine arylation

KW - mass spectrometry

KW - peptides

UR - https://www.scopus.com/pages/publications/85087631308

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JO - ChemBioChem

JF - ChemBioChem

IS - 21

ER -

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

Abstract

Keywords

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