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Issue 64, 2018
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Peptide self-cleavage at a canaline residue: application to a solubilizing tag system for native chemical ligation

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Abstract

Canaline (Can) is a non-proteinogenic amino acid containing an aminooxy group in its side chain. Can-containing peptides can be synthesized by standard Fmoc SPPS using Fmoc-Can(2-Cl-Trt). Here, for the first time, a Can residue within a peptide sequence was found to spontaneously cleave the main chain amide bond under slightly acidic conditions (pH 4–5). Contrastingly, Can-containing peptides are completely stable under the acidic conditions for HPLC purification (pH ca. 2) and under the neutral conditions for native chemical ligation (NCL). Taking advantage of these unique pH-dependent properties of Can, a novel solubilizing tag system for NCL-mediated protein synthesis using (Lys/Arg)n-Can was developed.

Graphical abstract: Peptide self-cleavage at a canaline residue: application to a solubilizing tag system for native chemical ligation

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Publication details

The article was received on 08 Jun 2018, accepted on 16 Jul 2018 and first published on 17 Jul 2018


Article type: Communication
DOI: 10.1039/C8CC04579H
Citation: Chem. Commun., 2018,54, 8861-8864

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    Peptide self-cleavage at a canaline residue: application to a solubilizing tag system for native chemical ligation

    S. Tsuda, H. Nishio and T. Yoshiya, Chem. Commun., 2018, 54, 8861
    DOI: 10.1039/C8CC04579H

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