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A New Highly Versatile Handle for Chemistry on a Solid Support: The Pipecolic Linker†

Authors

  • Dr. Nicolas Masurier,

    Corresponding author
    1. Institut des Biomolécules Max Mousseron IBMM, UMR CNRS 5247, 15 avenue Charles Flahault, 34000 Montpellier (France), Fax: (+33) 467548654
    • Institut des Biomolécules Max Mousseron IBMM, UMR CNRS 5247, 15 avenue Charles Flahault, 34000 Montpellier (France), Fax: (+33) 467548654
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  • Dr. Paweł Zajdel,

    1. Department of Medicinal Chemistry, Jagiellonian University Medical College, 9 Medyczna Street, 30-688 Kraków (Poland)
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  • Dr. Pascal Verdié,

    1. Institut des Biomolécules Max Mousseron IBMM, UMR CNRS 5247, 15 avenue Charles Flahault, 34000 Montpellier (France), Fax: (+33) 467548654
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  • Prof. Maciej Pawłowski,

    1. Department of Medicinal Chemistry, Jagiellonian University Medical College, 9 Medyczna Street, 30-688 Kraków (Poland)
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  • Dr. Muriel Amblard,

    1. Institut des Biomolécules Max Mousseron IBMM, UMR CNRS 5247, 15 avenue Charles Flahault, 34000 Montpellier (France), Fax: (+33) 467548654
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  • Prof. Jean Martinez,

    1. Institut des Biomolécules Max Mousseron IBMM, UMR CNRS 5247, 15 avenue Charles Flahault, 34000 Montpellier (France), Fax: (+33) 467548654
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  • Prof. Gilles Subra

    1. Institut des Biomolécules Max Mousseron IBMM, UMR CNRS 5247, 15 avenue Charles Flahault, 34000 Montpellier (France), Fax: (+33) 467548654
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  • †

    Part 2; for Part 1, see: P. Zajdel, G. Nomezine, N. Masurier, M. Amblard, M. Pawłowski, J. Martinez, G. Subra, Chem. Eur. J. 2010, 16, 7547–7553.

Abstract

original image

The versatility of the pipecolic linker (Pip-linker) is illustrated by the synthesis of modified amino acids, C-terminal-modified pseudopeptides, and cyclic peptides, through side-chain anchoring of a lysine residue (see figure). Introduction of the first residue was easily accomplished and the Pip-linker revealed to be robust enough to support various chemical modifications.

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Article Information

DOI

10.1002/chem.201201452

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Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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Keywords

  • C-terminal peptide alcohols;
  • cyclic peptides;
  • pipecolic linker;
  • solid-phase synthesis;
  • ureidopeptides

Publication History

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  • Version of record online:
  • Manuscript Received:

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  • IBMM

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  2. 2Prabhakar Cherkupally, Gerardo A. Acosta, Suhas Ramesh, Beatriz G. De la Torre, Thavendran Govender, Hendrik G. Kruger, Fernando Albericio, Solid-phase peptide synthesis (SPPS), C-terminal vs. side-chain anchoring: a reality or a myth, Amino Acids, 2014, 46, 8, 1827CrossRef
  3. 3N.K. Terrett, Combinatorial Chemistry Online, Combinatorial Chemistry - an Online Journal, 2013, 15, 4, 13CrossRef
  4. 4Paweł Zajdel, Nicolas Masurier, Vittorio Canale, Pascal Verdie, Muriel Amblard, Maciej Pawłowski, Jean Martinez, Gilles Subra, The pipecolic linker—an acid-labile handle for derivatization of secondary amines on a solid-support. Part 3, Tetrahedron Letters, 2013, 54, 8, 998CrossRef
  5. 5Mirna El Khatib, Mohamed Elagawany, Eray Çalışkan, Emily Faith Davis, Hassan M. Faidallah, Said A. El-feky, Alan R. Katritzky, Total synthesis of cyclic heptapeptide Rolloamide B, Chemical Communications, 2013, 49, 26, 2631CrossRef