A Cyclopropene Electrophile that Targets Glutathione S‐Transferase Omega‐1 in Cells. (26th July 2019)

• Record Type: Journal Article
• Authors: Wørmer, Gustav J.; Hansen, Bente K.; Palmfeldt, Johan; Poulsen, Thomas B.
• Is Part Of: Angewandte Chemie. Volume 131:Number 34(2019)
• Page Start: 12044
• Page End: 12048
• Publication Date: 2019-07-26
• Subjects: Bioorthogonale Chemie -- Chemische Proteomik -- Cyclopropen -- Elektrophile -- GSTO1-Inhibition; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201907520
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: Cyclopropenes are an important new addition to the portfolio of functional groups that can be used for bioorthogonal couplings. The inert nature of these highly strained compounds in complex biological systems is almost counterintuitive given their established electrophilic properties in organic synthesis. Here we provide the first demonstration of a cyclopropene that is capable of direct conjugation to protein targets in cells and show that this compound preferentially alkylates the active site cysteine of glutathione S‐transferase omega‐1 (GSTO1). Abstract : Reaktivdreieck : Das erste Beispiel eines Cyclopropens mit kovalenter Reaktivität in Zellen wird vorgestellt. Die Sonde reagiert mit Thiolen in vitro durch Fragmentierung des Cyclopropenrings und alkyliert das aktive Cystein der Glutathion‐S‐Transferase Omega‐1 in Zellen.