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Synthesis of Antimicrobial Lipopeptides Using the “CLipPA” Thiol-Ene Reaction

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Peptide Synthesis

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

Abstract

Cysteine Lipidation on a Peptide or Amino acid (CLipPA) technology provides a facile method for the lipidation of unprotected peptides containing a free thiol group by using a “click” radical-initiated thiol-ene reaction to effect addition to a vinyl ester. The methodology is highly versatile, leading to high conversion rates while maintaining excellent chemoselectivity and tolerance for a large variety of peptide substrates and functional groups. Herein we describe the simple general procedure for the synthesis of a focused library of bioactive S-lipidated antimicrobial peptides via late-stage derivatization using solution-phase CLipPA lipidation.

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Author information

Authors and Affiliations

  1. School of Chemical Sciences, The University of Auckland, Auckland, New Zealand

    Yann O. Hermant, Alan J. Cameron, Paul W. R. Harris & Margaret A. Brimble

  2. The Maurice Wilkins Centre for Molecular Biodiscovery, The University of Auckland, Auckland, New Zealand

    Yann O. Hermant, Alan J. Cameron, Paul W. R. Harris & Margaret A. Brimble

  3. School of Biological Sciences, The University of Auckland, Auckland, New Zealand

    Yann O. Hermant, Alan J. Cameron, Paul W. R. Harris & Margaret A. Brimble

Authors
  1. Yann O. Hermant
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  2. Alan J. Cameron
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  3. Paul W. R. Harris
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  4. Margaret A. Brimble
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Corresponding author

Correspondence to Margaret A. Brimble .

Editor information

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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Hermant, Y.O., Cameron, A.J., Harris, P.W.R., Brimble, M.A. (2020). Synthesis of Antimicrobial Lipopeptides Using the “CLipPA” Thiol-Ene Reaction. 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_18

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  • DOI: https://doi.org/10.1007/978-1-0716-0227-0_18

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  • Publisher Name: Humana, New York, NY

  • Print ISBN: 978-1-0716-0226-3

  • Online ISBN: 978-1-0716-0227-0

  • eBook Packages: Springer Protocols

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