The National Institutes of General Medical Sciences, Department of Health and Human Services supported this investigation through grant no. GM066153. Dr. Gary Allred of Synthonix provided many of the boronic acids used in our studies.
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Communication
A Copper-Catalyzed, pH-Neutral Construction of High-Enantiopurity Peptidyl Ketones from Peptidic S-Acylthiosalicylamides in Air at Room Temperature†
Article first published online: 14 JAN 2009
DOI: 10.1002/anie.200804524
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Liebeskind, Lanny S., Yang, H. and Li, H. (2009), A Copper-Catalyzed, pH-Neutral Construction of High-Enantiopurity Peptidyl Ketones from Peptidic S-Acylthiosalicylamides in Air at Room Temperature. Angew. Chem. Int. Ed., 48: 1417–1421. doi: 10.1002/anie.200804524
- †
Publication History
- Issue published online: 30 JAN 2009
- Article first published online: 14 JAN 2009
- Manuscript Received: 14 SEP 2008
Funded by
- National Institutes of General Medical Sciences, Department of Health and Human Services. Grant Number: GM066153
Keywords:
- copper;
- cross-coupling;
- peptidomimetics;
- protein modifications;
- synthetic methods
Abstract
A copper-catalyzed transformation of peptidic thiol esters and boronic acids gives peptidyl ketones and takes place in DMF or DMF/H2O at room temperature in air (see scheme). This aerobic reaction only occurs at a thiol ester group capable of coordinating to Cu through its appendage on the sulfur center and is not hampered by racemization of the reactants or products.