reviewChemical ReviewsMay 3, 2019Closed access

Native Chemical Ligation and Extended Methods: Mechanisms, Catalysis, Scope, and Limitations

Centre National de la Recherche Scientifique · Université de Lille · +4 more institutions

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Abstract

The native chemical ligation reaction (NCL) involves reacting a C-terminal peptide thioester with an N-terminal cysteinyl peptide to produce a native peptide bond between the two fragments. This reaction has considerably extended the size of polypeptides and proteins that can be produced by total synthesis and has also numerous applications in bioconjugation, polymer synthesis, material science, and micro- and nanotechnology research. The aim of the present review is to provide a thorough mechanistic overview of NCL and extended methods. The most relevant properties of peptide thioesters, Cys peptides, and common solvents, reagents, additives, and catalysts used for these ligations are presented. Mechanisms,…

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