Formation and Rearrangement of Homoserine Depsipeptides and Depsiproteins in the α‐Ketoacid–Hydroxylamine Ligation with 5‐Oxaproline1. Issue 45 (22nd September 2014)

• Record Type: Journal Article
• Authors: Wucherpfennig, Thomas G.; Rohrbacher, Florian; Pattabiraman, Vijaya R.; Bode, Jeffrey W.
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 45(2014)
• Page Start: 12244
• Page End: 12247
• Publication Date: 2014-09-22
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201406097
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The primary products of the chemical ligation of α‐ketoacids and 5‐oxaproline peptides are esters, rather than the previously reported amides. The depsipeptide product rapidly rearranges to the amide in basic buffers. The formation of esters sheds light on possible mechanisms for the type II KAHA ligations and opens an avenue for the chemical synthesis of depsiproteins.</p> </abstract>