Gold-promoted arylation of biomolecules: selenocysteine chemoselective modification by cyclometallated gold(III) compounds - Université de Pau et des Pays de l'Adour Accéder directement au contenu
Poster De Conférence Année : 2024

Gold-promoted arylation of biomolecules: selenocysteine chemoselective modification by cyclometallated gold(III) compounds

Résumé

A low pKa (5.2), high polarizable volume (3.8 Å), and proneness to oxidation under ambient conditions make selenocysteine (Sec, U) a unique, natural reactive handle present in most organisms across all domains of life1. Sec modification offers a unique and unexplored potential for site-selective modification and probing of proteins. Our investigation is focused on the use of cyclometallated gold(III) compounds for the chemoselective arylation of selenobiomolecules2. Here, the ability of several organometallic gold(III) compounds to promote the C-Se coupling in the active sites of Glutathion Peroxidase and Thiroedoxin Reductase was studied by liquid chromatography coupled to electrospray tandem mass spectrometry. The conditions enabling the selective arylation of Se over S were found in selenoproteins, containing both Sec and Cys. Moreover, in competitive experiments, selenopeptides are preferentially arylated by gold(III) compounds, even in the presence of large excess of their Cys counterparts.
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Dates et versions

hal-04524762 , version 1 (28-03-2024)

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  • HAL Id : hal-04524762 , version 1

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Ioannis Kanavos, Douglas Hideki Nakahata, Raphael Enoque Ferraz de Paiva, Luisa Ronga. Gold-promoted arylation of biomolecules: selenocysteine chemoselective modification by cyclometallated gold(III) compounds. BioNEXT: AEBIN young Researchers Symposium, Mar 2024, San Sebastian, Spain. ⟨hal-04524762⟩
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