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Native Chemical Ligation and Extended Methods: Mechanisms, Catalysis, Scope, and Limitations
Vangelis Agouridas1, Ouafâa El Mahdi2, Vincent Diemer1
1UMR CNRS 8204, Centre d'Immunité et d'Infection de Lille , University of Lille, CNRS, Institut Pasteur de Lille , F-59000 Lille , France.
Chemical Reviews
|May 4, 2019
Summary
Native chemical ligation (NCL) enables peptide synthesis by joining peptide thioesters and cysteinyl peptides. This review details NCL mechanisms, limitations, and advanced methods using surrogates for broader applications.
Area of Science:
- Chemical Biology
- Organic Chemistry
- Biochemistry
Background:
- Native chemical ligation (NCL) is a key reaction for synthesizing large peptides and proteins.
- NCL has broad applications in bioconjugation, polymer synthesis, and nanotechnology.
Purpose of the Study:
- To provide a comprehensive mechanistic overview of NCL and its extended methodologies.
- To discuss the properties of key components and reagents used in NCL.
- To explore limitations and advanced strategies in peptide synthesis.
Main Methods:
- Review of mechanistic insights from computational and physical chemistry studies.
- Analysis of peptide thioesters, cysteinyl peptides, solvents, reagents, and catalysts.
- Examination of acyl shift systems and thiol-based auxiliaries.
Main Results:
- Detailed mechanistic understanding of NCL and related reactions.
- Discussion of factors influencing selectivity and reactivity.
- Presentation of thioester and selenoester surrogates and their mechanisms.
Conclusions:
- NCL is a powerful tool for peptide synthesis and bioconjugation.
- Understanding reaction mechanisms is crucial for optimizing NCL and developing new methods.
- Advanced surrogates and auxiliaries expand the scope and efficiency of NCL.
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