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Article Dans Une Revue ACS Macro Letters Année : 2019

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

Résumé

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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Dates et versions

hal-02397850 , version 1 (17-04-2020)

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Marie Rosselin, Ye Xiao, Ludovic Belhomme, Sébastien Lecommandoux, Elisabeth Garanger. Expanding the Toolbox of Chemoselective Modifications of Protein-Like Polymers at Methionine Residues. ACS Macro Letters, 2019, 8 (12), pp.1648-1653. ⟨10.1021/acsmacrolett.9b00862⟩. ⟨hal-02397850⟩
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