Expanding the Toolbox of Chemoselective Modifications of Protein-Like Polymers at Methionine Residues

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Rosselin, Marie | Xiao, Ye | Belhomme, Ludovic | Lecommandoux, Sébastien | Garanger, Elisabeth

Edité par CCSD ; Washington, D.C : American Chemical Society -

International audience. Selective modifications at methionyl residues in proteins have attracted particular attention in recent years. Previously described methods to chemoselectively modify the methionine side chain in elastin-like polypeptides (ELPs) involved nucleophilic addition using alkyl halides or epoxides yielding a sulfonium group with a positive charge strongly affecting ELPs’ physicochemical properties, in particular their thermal responsiveness. We herein explored the recently reported ReACT method (Redox-Activated Chemical Tagging) based on the use of oxaziridine derivatives, yielding an uncharged sulfimide as an alternative route for chemoselective modifications of methionine-containing ELPs in aqueous medium. The different synthetic strategies are herein compared in order to provide a furnished toolbox for further biorthogonal postmodifications of any protein polymers.

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