Enzyme-Catalyzed Macrocyclization of Long Unprotected Peptides

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• 作者：Chi Zhang ; Peng Dai ; Alexander M. Spokoyny ; Bradley L. Pentelute
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：July 18, 2014
• 年：2014
• 卷：16
• 期：14
• 页码：3652-3655
• 全文大小：292K
• ISSN：1523-7052

文摘

A glutathione S-transferase (GST) catalyzed macrocyclization reaction for peptides up to 40 amino acids in length is reported. GST catalyzes the selective S_NAr reaction between an N-terminal glutathione (GSH, 纬-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.