ArticleFrontiers in chemistry2014
Realizing serine/threonine ligation: scope and limitations and mechanistic implication thereof.
Article in Frontiers in chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 35 citations in OpenAlex.
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- Preparation of Peptide C-Terminal Salicylaldehyde Ester Surrogates via a Hydrazide-Based Oxidation and Phenolysis Strategy.Methods in molecular biology (Clifton, N.J.) · 2025Article
- An Enabling Peptide Ligation Induced by Thiol-Salicylaldehyde Ester for Chemical Protein Synthesis.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Chemische Synthese und Semisynthese von lipidierten Proteinen.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Review
- Chemical Synthesis and Semisynthesis of Lipidated Proteins.Angewandte Chemie (International ed. in English) · 2022Review
- Enabling chemical protein (semi)synthesisChemical science · 2022Article
- An explorative study towards the chemical synthesis of the immunoglobulin G1 Fc CH3 domain.Journal of peptide science : an official publication of the European Peptide Society · 2018Article
- Fully Synthetic Granulocyte Colony-Stimulating Factor Enabled by Isonitrile-Mediated Coupling of Large, Side-Chain-Unprotected Peptides.Journal of the American Chemical Society · 2015Article
- Chemical and biological tools for the preparation of modified histone proteins.Topics in current chemistry · 2015Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Serine/Threonine ligation (STL) has emerged as an alternative tool for protein chemical synthesis, bioconjugations as well as macrocyclization of peptides of various sizes. Owning to the high abundance of Ser/Thr residues in natural peptides and proteins, STL is expected to find a wide range of applications in chemical biology research. Herein, we have fully investigated the compatibility of the STL strategy for X-Ser/Thr ligation sites, where X is any of the 20 naturally occurring amino acids. Our studies have shown that 17 amino acids are suitable for ligation, while Asp, Glu, and Lys are not compatible. Among the working 17 C-terminal amino acids, the retarded reaction resulted from the bulky β-branched amino acid (Thr, Val, and Ile) is not seen under the current ligation condition. We have also investigated the chemoselectivity involving the amino group of the internal lysine which may compete with the N-terminal Ser/Thr for reaction with the C-terminal salicylaldehyde (SAL) ester aldehyde group. The result suggested that the free internal amino group does not adversely slow down the ligation rate.
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