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ferricyanide-Promoted Oxidative Activation and Ligation of Protein Thioacids in Neutral Aqueous Media

CCS Chemistry 2024年第8期6卷 2031-2043页

作者： Guo-Chao Chu Lu-Jun Liang Rui Zhao Yan-Yan Guo Chun-Tong Li Chong Zuo Huasong Ai Xiao Hua Zi-Chen Li Yi-Ming Li Lei Liu NewCornerstone Science Laboratory Tsinghua-Peking Center for Life SciencesMinistry of Education Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical BiologyCenter for Synthetic and Systems BiologyDepartment of ChemistryTsinghua UniversityBeijing 100084 School of Food and Biological Engineering Hefei University of TechnologyHefei 230009 Center for BioAnalytical Chemistry Hefei National Laboratory of Physical Science at MicroscaleUniversity of Science and Technology of ChinaHefei 230026 Department of Chemistry University of Science and Technology of ChinaHefei 230026

ferricyanide-promoted oxidative activation of Nacylatedα-aminothioacids for amide bond formation withα-aminonitriles was recently shown to be a plausible pathway for prebiotic peptide *** we describe the finding that by adding sodium azide and thiols,ferricyanide oxidation can elicit highly efficient and clean conversion of fully unprotected peptide or protein thioacids in neutral aqueous media to the corresponding *** transformation enables the development of ferricyanide-promoted thioacid-based native chemical ligation(NCL)as a new redox-based method for chemical protein synthesis,which does not need to change pH and is therefore operationally easy for ligation at small *** effectiveness of the ferricyanide-promoted thioacid-based NCL was illustrated by synthesis of an ISG15-modified MDA5 segment under nondenaturing conditions and synthesis of an acetylated ubiquitin(Ub)-modified histone H2A through an N-to-C sequential *** work broadens the concept of on-demand oxidative activation strategy for protein ligation and provides a new useful supplement to the repertoire of methods for chemical protein synthesis,particularly for studies on proteins carrying Ub family modifications.

关键词： chemical protein synthesis protein thioacid ferricyanide oxidation native chemical ligation ubiquitin family modifications

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