Exploring the Chemoselectivity towards Cysteine Arylation by Cyclometallated Au(III)Compounds: New Mechanistic Insights

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

doi:10.1002/cbic.202000262

Exploring the Chemoselectivity towards Cysteine Arylation by Cyclometallated Au(III)Compounds: New Mechanistic Insights

Sophie R. Thomas, Riccardo Bonsignore, Jorge Sanchez Escudero, Samuel M. Meier-Menches, Christopher M. Brown, Michael O. Wolf, Giampaolo Barone, Louis Y. P. Luk (Corresponding author), Angela Casini (Corresponding author)

Department of Analytical Chemistry

Publications: Contribution to journal › Article › Peer Reviewed

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: a european journal of chemical biology
Volume	21
Issue number	21
DOIs	https://doi.org/10.1002/cbic.202000262
Publication status	Published - 8 Jul 2020

Austrian Fields of Science 2012

106002 Biochemistry
106023 Molecular biology
301305 Medical chemistry

Keywords

chemoselectivity
cyclometallated gold complexes
cysteine arylation
mass spectrometry
peptides
GOLD(III) COMPLEXES
PROTEIN
FUNCTIONALIZATION
CATALYSIS
TOOL

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10.1002/cbic.202000262

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Thomas, S. R., Bonsignore, R., Sanchez Escudero, J., Meier-Menches, S. M., Brown, C. M., Wolf, M. O., Barone, G., Luk, L. Y. P., & Casini, A. (2020). Exploring the Chemoselectivity towards Cysteine Arylation by Cyclometallated Au(III)Compounds: New Mechanistic Insights. ChemBioChem: a european journal of chemical biology, 21(21), 3071-3076. https://doi.org/10.1002/cbic.202000262

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title = "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.",

keywords = "chemoselectivity, cyclometallated gold complexes, cysteine arylation, mass spectrometry, peptides, GOLD(III) COMPLEXES, PROTEIN, FUNCTIONALIZATION, CATALYSIS, TOOL",

author = "Thomas, {Sophie R.} and Riccardo Bonsignore and {Sanchez Escudero}, Jorge and Meier-Menches, {Samuel M.} and Brown, {Christopher M.} and Wolf, {Michael O.} and Giampaolo Barone and Luk, {Louis Y. P.} and Angela Casini",

note = "Publisher Copyright: {\textcopyright} 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA",

year = "2020",

month = jul,

day = "8",

doi = "10.1002/cbic.202000262",

language = "English",

volume = "21",

pages = "3071--3076",

journal = "ChemBioChem: a european journal of chemical biology",

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Thomas, SR, Bonsignore, R, Sanchez Escudero, J, Meier-Menches, SM, Brown, CM, Wolf, MO, Barone, G, Luk, LYP & Casini, A 2020, 'Exploring the Chemoselectivity towards Cysteine Arylation by Cyclometallated Au(III)Compounds: New Mechanistic Insights', ChemBioChem: a european journal of chemical biology, vol. 21, no. 21, pp. 3071-3076. https://doi.org/10.1002/cbic.202000262

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AU - Thomas, Sophie R.

AU - Bonsignore, Riccardo

AU - Sanchez Escudero, Jorge

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 - 2020/7/8

Y1 - 2020/7/8

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

KW - GOLD(III) COMPLEXES

KW - PROTEIN

KW - FUNCTIONALIZATION

KW - CATALYSIS

KW - TOOL

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DO - 10.1002/cbic.202000262

M3 - Article

SN - 1439-4227

VL - 21

SP - 3071

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JO - ChemBioChem: a european journal of chemical biology

JF - ChemBioChem: a european journal of chemical biology

IS - 21

ER -

Exploring the Chemoselectivity towards Cysteine Arylation by Cyclometallated Au(III)Compounds: New Mechanistic Insights

Abstract

Austrian Fields of Science 2012

Keywords

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