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Safety-catch linkers for Fmoc solid-phase synthesis of peptide thioesters and hydrazides by amide-to-imide activation
Journal of Peptide Science  (IF1.905),  Pub Date : 2021-09-09, DOI: 10.1002/psc.3364
Maciej P. Paprocki, Jakob E. Rasmussen, Kasper K. Sørensen, Knud J. Jensen

The use of C-terminal peptide thioesters and hydrazides in synthetic protein chemistry has inspired the search for optimal solid-phase peptide synthesis (SPPS) strategies for their assembly. However, peptide thioesters are not directly accessible by conventional Fmoc-SPPS owing to the nucleophilicity of the secondary amine required for Fmoc removal. Here, we report the mild and effective activation of the pGlu linker and a new safety-catch linker that was used for the convenient synthesis of peptide thioesters and hydrazides via efficient amide-to-imide activation followed by nucleophilic displacement.