Expanding the Toolbox of Chemoselective Modifications of Protein-Like Polymers at Methionine Residues,ACS Macro Letters

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Expanding the Toolbox of Chemoselective Modifications of Protein-Like Polymers at Methionine Residues
ACS Macro Letters ( IF 5.1 ) Pub Date : 2019-12-05 , DOI: 10.1021/acsmacrolett.9b00862
Marie Rosselin ₁ , Ye Xiao ₁ , Ludovic Belhomme ₁ , Sébastien Lecommandoux ₁ , Elisabeth Garanger ₁

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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.

中文翻译：

扩展在蛋氨酸残基上对蛋白质类聚合物进行化学选择性修饰的工具箱

近年来，蛋白质中甲硫氨酰残基的选择性修饰引起了人们的特别关注。先前描述的化学选择性修饰弹性蛋白样多肽 (ELP) 中蛋氨酸侧链的方法涉及使用卤代烷或环氧化物进行亲核加成，产生具有正电荷的锍基团，强烈影响 ELP 的物理化学性质，特别是它们的热响应性。我们在此探索了最近报道的 ReACT 方法（氧化还原活化化学标记），该方法基于使用恶氮丙啶衍生物，产生不带电荷的硫酰亚胺作为在水性介质中化学选择性修饰含蛋氨酸 ELP 的替代途径。

更新日期：2019-12-05

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