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

Chi Lung Lee; Han Liu; Clarence T.T. Wong; Hoi Yee Chow; Xuechen Li

doi:10.1021/jacs.6b04238

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

Chi Lung Lee, Han Liu, Clarence T.T. Wong, Hoi Yee Chow, Xuechen Li

Research output: Journal article publication › Journal article › Academic research › peer-review

72 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	10477-10484
Number of pages	8
Journal	Journal of the American Chemical Society
Volume	138
Issue number	33
DOIs	https://doi.org/10.1021/jacs.6b04238
Publication status	Published - 24 Aug 2016
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/jacs.6b04238

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abstract = "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.",

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AU - Lee, Chi Lung

AU - Liu, Han

AU - Wong, Clarence T.T.

AU - Chow, Hoi Yee

AU - Li, Xuechen

PY - 2016/8/24

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AB - 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.

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

Abstract

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