Journal
CHEMICAL COMMUNICATIONS
Volume 57, Issue 16, Pages 2081-2084Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0cc07747j
Keywords
-
Categories
Funding
- Australian Research Council [DP180101804, DP150100692]
- University of Melbourne
- Albert Shimmins Fund Award
Ask authors/readers for more resources
This study presents a novel macrolactonisation strategy using Ag(i)-promoted conversion of peptide thioamides to isoimide intermediates, which undergo site-selective intramolecular acyl transfer to generate the macrolactone.
Macrolactonisation of peptides to generate cyclic depsipeptides is often challenging due to the low nucleophilicity of hydroxyl groups, epimerisation, cyclodimerisation, and potential acyl transfer reactions of the ester. Herein, we report a novel macrolactonisation strategy employing a Ag(i)-promoted conversion of peptide thioamides to isoimide intermediates, which undergo site-selective intramolecular acyl transfer to serine/threonine side chains to generate the macrolactone.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available