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J Nat Prod. 2019 Aug 23;82(8):2152-2158. doi: 10.1021/acs.jnatprod.9b00111. Epub 2019 Aug 8.

An Orbitide from Ratibida columnifera Seed Containing 16 Amino Acid Residues.

Author information

1
School of Molecular Sciences , The University of Western Australia , 35 Stirling Highway , Crawley , WA 6009 , Australia.
2
Faculty of Medicine, School of Biomedical Sciences , The University of Queensland , Brisbane , QLD 4072 , Australia.

Abstract

Cyclic peptides are abundant in plants and have attracted interest due to their bioactivity and potential as drug scaffolds. Orbitides are head-to-tail cyclic peptides that are ribosomally synthesized, post-translationally modified, and lack disulfide bonds. All known orbitides contain 5-12 amino acid residues. Here we describe PLP-53, a novel orbitide from the seed of Ratibida columnifera. PLP-53 consists of 16 amino acids, four residues larger than any known orbitide. NMR structural studies showed that, compared to previously characterized orbitides, PLP-53 is more flexible and, under the studied conditions, did not adopt a single ordered conformation based on analysis of NOEs and chemical shifts.

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