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

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journal contribution
posted on 01.08.2016, 00:00 by Chi Lung Lee, Han Liu, Clarence T. T. Wong, Hoi Yee Chow, Xuechen Li
In this article, Ser/Thr ligationon/off has been realized to enable N-to-C successive peptide ligations using a salicylaldehyde semicarbazone (SALoff) group by in situ activation with pyruvic acid of the peptide SALoff ester into the peptide salicylaldehyde (SALon) 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.