Wikipedia defines a cyclic peptide as a polypeptide chain wherein the amino terminus and the carboxyl terminus, amino terminus and sidechain, carboxyl terminus and sidechain or sidechain and sidechain are linked to form a ring.  The awkwardness of this definition reflects the multitude of ways that peptide-like sequences can cross-link to form macrocycles.  Together with the great diversity of non-standard amino acid monomers, the myriad topologies and architectures available to cyclic peptides enable the  chemical diversity that has resulted in their prevalence amongst natural products and synthetic small molecule libraries.  In this presentation, we consider some of the informatics challenges of recognizing and representing homodetic and heterodetic peptides, stapled peptides, disulfide bridge patterns and other polycyclic peptides.  Amongst the complications are that covalently cross-linked sidechains may have multiple possible (degenerate) primary sequences, requiring the selection of a preferred canonical form during biological registration.  This talk will present examples and statistics drawn from the PubChem and ChEMBL databases.

Classification, representation, and analysis of cyclic peptides and peptide-like analogs

248th National Meeting (2014)

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