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Protecting Groups in Peptide Synthesis

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Peptide Synthesis

Part of the book series: Methods in Molecular Biology ((MIMB,volume 2103))

Abstract

The protection of amino acid reactive functionalities including the α-amino group, the side chain (amines, carboxylic acids, alcohols, and thiols), or the carboxylic acid terminus is an essential strategy in peptide chemistry. This is mandatory to prevent polymerization of the amino acids and to minimize undesirable side reactions during the synthetic process. Proper protecting group manipulation strategies can maximize the yield of the desired product or allow the construction of complex peptide-based structures. Thus, the compatibility and orthogonality of each protecting group are key to achieve the proper control of molecular structure. Herein, we describe some common protecting groups and their general unmasking methods, in order to mask and expose amine, carboxylic acid, alcohol, and thiol functionalities to achieve the synthesis of peptides and related molecules.

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Acknowledgments

This work was funded by the National Institute of Health-NIGMS, the Nebraska Center for Molecular Target Discovery and Development (1P20GM121316-01A1, PI: Robert Lewis, Project Leader, M.C.-S.), and the American Chemical Society, PRF# 57434-DNI7 (M.C.-S.).

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Authors and Affiliations

  1. Department of Pharmaceutical Sciences, College of Pharmacy, University of Nebraska Medical Center, Omaha, NE, USA

    Martin Conda-Sheridan & Maddeboina Krishnaiah

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  1. Martin Conda-Sheridan
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  2. Maddeboina Krishnaiah
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Correspondence to Martin Conda-Sheridan .

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Editors and Affiliations

  1. School of Chemistry and Molecular Biosciences, The University of Queensland, St. Lucia, QLD, Australia

    Waleed M. Hussein

  2. School of Chemistry and Molecular Biosciences, The University of Queensland, St. Lucia, QLD, Australia

    Mariusz Skwarczynski

  3. School of Chemistry and Molecular Biosciences, The University of Queensland, St. Lucia, QLD, Australia

    Istvan Toth

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Conda-Sheridan, M., Krishnaiah, M. (2020). Protecting Groups in Peptide Synthesis. In: Hussein, W., Skwarczynski, M., Toth, I. (eds) Peptide Synthesis. Methods in Molecular Biology, vol 2103. Humana, New York, NY. https://doi.org/10.1007/978-1-0716-0227-0_7

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  • DOI: https://doi.org/10.1007/978-1-0716-0227-0_7

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