Revisiting N-to-O Acyl Shift for Synthesis of Natural Product-like Cyclic Depsipeptides
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- 作者：Joshua Schwochert ; Cameron Pye ; Christopher Ahlbach ; Yashar Abdollahian ; Kathleen Farley ; Bhagyashree Khunte ; Chris Limberakis ; Amit S. Kalgutkar ; Heather Eng ; Michael J. Shapiro ; Alan M. Mathiowetz ; David A. Price ; Spiros Liras ; R. Scott Lokey
- 刊名：Organic Letters
- 出版年：2014
- 出版时间：December 5, 2014
- 年：2014
- 卷：16
- 期：23
- 页码：6088-6091
- 全文大小：278K
- ISSN：1523-7052
文摘
Despite the prevalence of head-to-side chain threonine linkages in natural products, their incorporation has been underexplored in synthetic cyclic peptides. Herein we investigate a cyclic peptide scaffold able to undergo an N鈥?i>O acyl rearrangement. Upon acylation of the amine with diverse carboxylic acids, the resulting cyclic depsipeptides displayed favorable cellular permeability and a conformation similar to the parent peptide. The rearrangement was found to be scaffold and conformation dependent as evidenced by molecular dynamics experiments.