Synthesis of bioactive and stabilized cyclic peptides by macrocyclization using C(sp3)–H activation

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Synthesis of bioactive and stabilized cyclic peptides by macrocyclization using C(sp3)-H activation.

Cyclic peptides have attracted increasing attention in recent years due to their ability to inhibit protein-protein interactions. Current strategies to prepare cyclic peptides often rely on functional amino acid side chains or the incorporation of unnatural amino acids, thus limiting their structural diversity. Here, we describe the development of a highly versatile peptide macrocyclization str...

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Synthesis of bioactive and stabilized cyclic peptides by macrocyclization using C(sp3)–H activation† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc05530c Click here for additional data file.

Cyclic peptides have attracted increasing attention in recent years due to their ability to inhibit protein– protein interactions. Current strategies to prepare cyclic peptides often rely on functional amino acid side chains or the incorporation of unnatural amino acids, thus limiting their structural diversity. Here, we describe the development of a highly versatile peptide macrocyclization st...

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Enzyme-Catalyzed Macrocyclization of Long Unprotected Peptides

A glutathione S-transferase (GST) catalyzed macrocyclization reaction for peptides up to 40 amino acids in length is reported. GST catalyzes the selective S(N)Ar reaction between an N-terminal glutathione (GSH, γ-Glu-Cys-Gly) tag and a C-terminal perfluoroaryl-modified cysteine on the same polypeptide chain. Cyclic peptides ranging from 9 to 24 residues were quantitatively produced within 2 h i...

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ژورنال

عنوان ژورنال: Chemical Science

سال: 2017

ISSN: 2041-6520,2041-6539

DOI: 10.1039/c6sc05530c