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Keywords:

  • amides;
  • cleavage reactions;
  • peptides;
  • solvolysis;
  • zinc
Thumbnail image of graphical abstract

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.