Enzyme-Catalyzed Macrocyclization of Long Unprotected Peptides
Author(s)Zhang, Chi; Dai, Peng; Spokoyny, Alexander M.; Pentelute, Bradley L.
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A glutathione S-transferase (GST) catalyzed macrocyclization reaction for peptides up to 40 amino acids in length is reported. GST catalyzes the selective SNAr 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 in aqueous pH = 8 buffer at room temperature. The reaction was highly selective for cyclization at the GSH tag, enabling the combination of GST-catalyzed ligation with native chemical ligation to generate a large 40-residue peptide macrocycle.
DepartmentMassachusetts Institute of Technology. Department of Chemistry
American Chemical Society (ACS)
Zhang, Chi, Peng Dai, Alexander M. Spokoyny, and Bradley L. Pentelute. “Enzyme-Catalyzed Macrocyclization of Long Unprotected Peptides.” Organic Letters 16, no. 14 (July 18, 2014): 3652–3655.
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