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Side-Chain Anchoring Strategies for the Synthesis of Peptide Thioesters and Selenoesters

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Chemical Protein Synthesis

Part of the book series: Methods in Molecular Biology ((MIMB,volume 2530))

Abstract

Peptides bearing C-terminal thioester and selenoester functionalities are essential precursors for the chemical synthesis of larger proteins using ligation chemistry, including native chemical ligation (NCL) and diselenide-selenoester ligation (DSL). The use of a side-chain anchoring thioesterification or selenoesterification approach offers a robust method to access peptide thioesters or peptide selenoesters in excellent yields and in high purity. Importantly, this methodology overcomes solubility issues and epimerization of the C-terminal amino acid residue that can occur using solution-phase approaches. Detailed methods for the solid-phase synthesis of peptide thioesters and selenoesters using a side-chain anchoring approach are outlined in this article.

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Author information

Authors and Affiliations

  1. School of Chemistry, The University of Sydney, Sydney, NSW, Australia

    Lucas Kambanis & Sameer S. Kulkarni

  2. Australian Research Council Centre of Excellence for Innovations in Peptide and Protein Science, The University of Sydney, Sydney, NSW, Australia

    Lucas Kambanis, Sameer S. Kulkarni & Richard J. Payne

Authors
  1. Lucas Kambanis
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  2. Sameer S. Kulkarni
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  3. Richard J. Payne
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Corresponding author

Correspondence to Richard J. Payne .

Editor information

Editors and Affiliations

  1. Department of Chemistry, University of Hong Kong, Hong Kong, SAR, P. R, China

    Xuechen Li

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© 2022 The Author(s), under exclusive license to Springer Science+Business Media, LLC, part of Springer Nature

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Kambanis, L., Kulkarni, S.S., Payne, R.J. (2022). Side-Chain Anchoring Strategies for the Synthesis of Peptide Thioesters and Selenoesters. In: Li, X. (eds) Chemical Protein Synthesis. Methods in Molecular Biology, vol 2530. Humana, New York, NY. https://doi.org/10.1007/978-1-0716-2489-0_9

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  • DOI: https://doi.org/10.1007/978-1-0716-2489-0_9

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  • Publisher Name: Humana, New York, NY

  • Print ISBN: 978-1-0716-2488-3

  • Online ISBN: 978-1-0716-2489-0

  • eBook Packages: Springer Protocols

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