A New Method for Synthesis of Peptide Thioesters via Irreversible N-to-S Acyl Transfer

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• 作者：Ji-Shen Zheng ; Xin Chen ; Shan Tang ; Hao-Nan Chang ; Feng-Liang Wang ; Chao Zuo
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：September 19, 2014
• 年：2014
• 卷：16
• 期：18
• 页码：4908-4911
• 全文大小：375K
• ISSN：1523-7052

文摘

A new synthetic method for peptide thioesters is described using Fmoc solid-phase peptide synthesis (Fmoc-SPPS). This method employs a novel enamide motif to facilitate irreversible intramolecular N-to-S acyl migration, which can efficiently afford the desired peptide thioesters (3 h, 30 掳C) under the final trifluoroacetic acid (TFA) cleavage conditions. The acyl-transfer-mediated approach for synthesis of peptide thioesters tolerated different C-terminal residues and was used to synthesize human C鈥揅 motif chemokine 11 (hCCL11) via native chemical ligation.