Enabling N-to-C Ser/Thr Ligation for Convergent Protein Synthesis via Combining Chemical Ligation Approaches

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• 作者：Chi Lung Lee ; Han Liu ; Clarence T. T. Wong ; Hoi Yee Chow ; Xuechen Li
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：August 24, 2016
• 年：2016
• 卷：138
• 期：33
• 页码：10477-10484
• 全文大小：609K
• 年卷期：0
• ISSN：1520-5126

文摘

In this article, Ser/Thr ligation^on/off has been realized to enable N-to-C successive peptide ligations using a salicylaldehyde semicarbazone (SAL^off) group by in situ activation with pyruvic acid of the peptide SAL^off ester into the peptide salicylaldehyde (SAL^on) ester. In addition, a peptide with a C-terminal thioester and N-terminal Ser or Thr as the middle peptide segment can undergo one-pot Ser/Thr ligation and native chemical ligation in the N-to-C direction. The utility of this combined ligation strategy in the N-to-C direction has been showcased through the convergent assembly of a human cytokine protein sequence, GlcNAcylated interleukin-25.