This work is finantially supported by The Core Research for Evolutional Science and Technology (CREST), program of the Japan Science and Technology Agency (JST).
Zinc-Catalyzed Amide Cleavage and Esterification of β-Hydroxyethylamides†
Article first published online: 20 APR 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 23, pages 5723–5726, June 4, 2012
How to Cite
Kita, Y., Nishii, Y., Higuchi, T. and Mashima, K. (2012), Zinc-Catalyzed Amide Cleavage and Esterification of β-Hydroxyethylamides. Angew. Chem. Int. Ed., 51: 5723–5726. doi: 10.1002/anie.201201789
- Issue published online: 30 MAY 2012
- Article first published online: 20 APR 2012
- Manuscript Received: 6 MAR 2012
- Japan Science and Technology Agency (JST)
- cleavage reactions;
Snipping tool: Zn(OTf)2 is an efficient catalyst for selective cleavage of amides bearing a β-hydroxyethyl group on the nitrogen atom. The mechanism involves an N,O-acyl rearrangement and transesterification. This new catalytic system can be applied to sequence-specific peptide bond scission at the amine side of a serine residue. Tf=trifluoromethanesulfonyl.