Formation and Rearrangement of Homoserine Depsipeptides and Depsiproteins in the α‐Ketoacid–Hydroxylamine Ligation with 5‐Oxaproline |
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| Authors: | Thomas G Wucherpfennig Florian Rohrbacher Dr Vijaya R Pattabiraman Prof?Dr Jeffrey W Bode |
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| Institution: | 1. Laboratorium für Organische Chemie, Department of Chemistry and Applied Biosciences, ETH Zürich, 8093 Zürich (Switzerland) http://www.bode.ethz.ch;2. Institute of Transformative Bio‐Molecules (WPI‐ITbM), Nagoya University, Chikusa, Nagoya 464‐8602 (Japan) http://www.itbm.nagoya‐u.ac.jp |
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| Abstract: | 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. |
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| Keywords: | chemoselectivity depsipeptides ligation proteins reaction mechanisms |
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