학술논문
Revisiting N-to-O Acyl Shift for Synthesisof Natural Product-like Cyclic Depsipeptides.
Document Type
Article
Author
Source
Subject
*ACYL shifts
*DEPSIPEPTIDES synthesis
*THREONINE
*CYCLIC peptides
*NATURAL products
*SCAFFOLD proteins
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Language
ISSN
1523-7060
Abstract
Despitethe prevalence of head-to-side chain threonine linkagesin natural products, their incorporation has been underexplored insynthetic cyclic peptides. Herein we investigate a cyclic peptidescaffold able to undergo an N–Oacyl rearrangement. Upon acylation of the amine with diverse carboxylicacids, the resulting cyclic depsipeptides displayed favorable cellularpermeability and a conformation similar to the parent peptide. Therearrangement was found to be scaffold and conformation dependentas evidenced by molecular dynamics experiments. [ABSTRACT FROM AUTHOR]