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Thirteen decades of peptide synthesis: key developments in solid phase peptide synthesis and amide bond formation utilized in peptide ligation

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Abstract

A historical overview of peptide chemistry from T. Curtius to E. Fischer to M. Bergmann and L. Zervas is first presented. Next, the fundamentals of peptide synthesis with a focus on solid phase peptide synthesis by R. B. Merrifield are described. Immobilization strategies to attach the first amino acid to the resin, coupling strategies in stepwise peptide chain elongation, and approaches to synthesize difficult peptide sequences are also shown. A brief comparison between tert-butyloxycarbonyl (Boc)/benzyl (Bzl) strategy and 9-fluorenylmethoxycarbonyl (Fmoc)/tert-butyl (t -Bu) strategy utilized in solid phase peptide synthesis is given with an emphasis on the latter. Finally, the review focuses on the discovery and development of peptide ligation and the latest advances in this field including native amide bond formation strategies, these include the native chemical ligation, α-ketoacid–hydroxylamine ligation, and serine/threonine ligation which are the most commonly used chemoselective ligation methods that provide amide bond at the ligation site. This review provides an overview of the literature concerning the most important advances in the chemical synthesis of proteins and peptides covering the period from 1882 to 2017.

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Acknowledgements

The author gratefully acknowledges the financial support by Scientific Research Support Fund (SRSF) of Jordan within the Grant (Project MPH/2/03/2012). Furthermore, Dr. Michaela Mühlberg (Royal Society of Chemistry), Prof. Dr. Feras Alali (University of Qatar), and Eng. Rakeen Abuhanih (GMA Jordan) are thanked for careful proofreading and for the helpful discussions. The author also wishes to thank Prof. Dr. Christian P. R. Hackenberger (Leibniz—Institut für Molekulare Pharmakologie (FMP) and Humboldt Universität zu Berlin) for his valuable notes during the preparation of the manuscript.

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  1. Department of Chemistry, Faculty of Science, Al-Balqa Applied University, P.O. Box 19117, Al-Salt, Jordan

    Da’san M. M. Jaradat

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Handling Editor: J. D. Wade.

In memory of professors Theodor Curtius and Emil Fischer, the founders of peptide chemistry.

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Jaradat, D.M.M. Thirteen decades of peptide synthesis: key developments in solid phase peptide synthesis and amide bond formation utilized in peptide ligation. Amino Acids 50, 39–68 (2018). https://doi.org/10.1007/s00726-017-2516-0

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