Macrocyclic peptides used as drugs

Article By:

Daly, Norelle L. School of Pharmacy and Molecular Sciences, James Cook University, Smithfield, Cairns, Queensland, Australia.

Last reviewed:2014

DOI:https://doi.org/10.1036/1097-8542.YB150950

Macrocyclic peptides are a remarkably diverse family of peptides found in a range of organisms, including bacteria, plants, fungi, and mammals. The common feature defining macrocyclic peptides is a ring structure, but a range of linkages can be involved, including N-terminus–to–C-terminus (head-to-tail), head–to–side-chain, side-chain–to–tail, and side-chain–to–side-chain linkages. These different linkages result in a wide array of structures. In addition, the peptide sizes vary significantly, with peptides ranging from less than 10 residues to proteins of approximately 70 residues. Nonnative residues, which can enhance biological stability, are often present in the smaller peptides, whereas the larger peptides tend to have predominantly standard residues. This distinction is a reflection of the fact that smaller peptides are often biosynthesized by nonribosomal pathways, whereas larger macrocyclic peptides are generally gene-encoded.

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