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Dr. Yusuke Kita, Yuji Nishii, Takafumi Higuchi and Prof. Dr. Kazushi Mashima Zinc-Catalyzed Amide Cleavage and Esterification of β-Hydroxyethylamides Angewandte Chemie International Edition 51

Article first published online: 20 APR 2012 | DOI: 10.1002/anie.201201789

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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.

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