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Molecules 2018, 23(7), 1779; https://doi.org/10.3390/molecules23071779

Cyclic Octamer Peptoids: Simplified Isosters of Bioactive Fungal Cyclodepsipeptides

1
Department of Chemistry and Biology “A. Zambelli”, University of Salerno, Via Giovanni Paolo II, 132, 84084 Fisciano, Italy
2
Graduate School of Bioresources, Mie University, 1577 Kurimamachiya-cho, Tsu 514-8507, Japan
*
Authors to whom correspondence should be addressed.
Received: 6 July 2018 / Revised: 13 July 2018 / Accepted: 14 July 2018 / Published: 19 July 2018
(This article belongs to the Special Issue Cyclic Peptides)
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Abstract

Cyclic peptoids have recently emerged as an important class of bioactive scaffolds with unique conformational properties and excellent metabolic stabilities. In this paper, we describe the design and synthesis of novel cyclic octamer peptoids as simplified isosters of mycotoxin depsipeptides bassianolide, verticilide A1, PF1022A and PF1022B. We also examine their complexing abilities in the presence of sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (TFPB) salt and explore their general insecticidal activity. Finally, we discuss the possible relationship between structural features of free and Na+-complexed cyclic octamer peptoids and bioactivities in light of conformational isomerism, a crucial factor affecting cyclic peptoids’ biomimetic potentials. View Full-Text
Keywords: cyclic peptoids; cyclodepsipeptides; insecticidal activity; conformational isomerism; structure-based design; peptidomimetics cyclic peptoids; cyclodepsipeptides; insecticidal activity; conformational isomerism; structure-based design; peptidomimetics
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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D’Amato, A.; Della Sala, G.; Izzo, I.; Costabile, C.; Masuda, Y.; De Riccardis, F. Cyclic Octamer Peptoids: Simplified Isosters of Bioactive Fungal Cyclodepsipeptides. Molecules 2018, 23, 1779.

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