학술논문

Revisiting N-to-O Acyl Shift for Synthesisof Natural Product-like Cyclic Depsipeptides.
Document Type
Article
Source
Organic Letters. Dec2014, Vol. 16 Issue 23, p6088-6091. 4p.
Subject
*ACYL shifts
*DEPSIPEPTIDES synthesis
*THREONINE
*CYCLIC peptides
*NATURAL products
*SCAFFOLD proteins
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]