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.
Highlights
While the vast inventory of natural products finds its limits in the finiteness of biosynthetic pathways [1], the synthesis of non-natural analogues has no boundaries [2]
Their excellent biomimetic properties have been confirmed by a recent study in which abiotic hexamer cyclopeptoids evoked potent cytotoxic activities against cancer cell lines [12]
We report the design and synthesis of structural congeners of cyclic octamer depsipeptides bassianolide (Bs, 1) [13,14], verticilide A1 (VtA1, 2) [15,16] and
Summary
While the vast inventory of natural products finds its limits in the finiteness of biosynthetic pathways [1], the synthesis of non-natural analogues has no boundaries [2] For their distinct conformational properties [3], their excellent biostabilities [4] and straightforward modular construction [5], peptoids (i.e., oligomers of N-substituted glycines) [6] represent a formidable class of biomimetic compounds with striking bio- and pharmacological activities [7,8]. Cyclic peptoids hold a special status for their intrinsic ability to adopt compact folded conformations [9,10] and exhibit conspicuous therapeutic properties [9,11] Their excellent biomimetic properties have been confirmed by a recent study in which abiotic hexamer cyclopeptoids (mimicking depsipeptide mycotoxins of the enniatins class) evoked potent cytotoxic activities against cancer cell lines [12]. We will evaluate both the advantages and drawbacks related to the use of cyclic peptoids as natural products mimics
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