Protecting groups in peptide synthesis

Martin Conda-Sheridan, Maddeboina Krishnaiah

Research output: Chapter in Book/Report/Conference proceedingChapter

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.

Original languageEnglish (US)
Title of host publicationMethods in Molecular Biology
PublisherHumana Press Inc.
Pages111-128
Number of pages18
DOIs
StatePublished - 2020

Publication series

NameMethods in Molecular Biology
Volume2103
ISSN (Print)1064-3745
ISSN (Electronic)1940-6029

Keywords

  • Amino acid side chains
  • Amino acids
  • Protecting groups
  • Protection of amines
  • Solid-phase peptide synthesis

ASJC Scopus subject areas

  • Molecular Biology
  • Genetics

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  • Cite this

    Conda-Sheridan, M., & Krishnaiah, M. (2020). Protecting groups in peptide synthesis. In Methods in Molecular Biology (pp. 111-128). (Methods in Molecular Biology; Vol. 2103). Humana Press Inc.. https://doi.org/10.1007/978-1-0716-0227-0_7