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Biron, Éric

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Biron

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Éric

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Université Laval. Faculté de pharmacie

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ncf11849118

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  • PublicationRestreint
    Synthetic Strategies for Macrocyclic Peptides
    (John Wiley & Sons, 2017-08-18) Biron, Éric; Vézina-Dawod, Simon; Bédard, François
    Peptide macrocycles form an outstanding class of natural and synthetic bioactive compounds. This chapter discusses synthetic strategies for the final ring‐closing reaction by the widely employed and versatile processes of lactamization, lactonization, and disulfide bridge formation. According to the nature of the chemical bond found in the backbone, cyclic peptides can be classified in two major categories: homodetic peptides and heterodetic peptides. In principle, all methods suitable for peptide bond formation can be applied for head‐to‐tail macrocyclization of linear peptides; however the reaction usually proceeds more slowly than the corresponding bimolecular version. During synthesis design, the C‐terminal amino acid of the linear precursor and the coupling reagent should be carefully chosen to minimize epimerization at the C‐terminal residue during cyclization. In many cases, the solution‐phase strategy is the best choice for performing the macrocyclization step, especially when larger quantities of cyclic peptide are required.