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Singlet oxygen-mediated one-pot chemoselective peptide–peptide ligation

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Abstract

We here describe a furan oxidation based site-specific chemical ligation approach using unprotected peptide segments. This approach involves two steps: after photooxidation of a furan-containing peptide, ligation is achieved by reaction of the unmasked keto–enal with C- or N-terminal α-nucleophilic moieties of the second peptide such as hydrazine or hydrazide to form a pyridazinium or pyrrolidinone linkage respectively.

Graphical abstract: Singlet oxygen-mediated one-pot chemoselective peptide–peptide ligation

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Publication details

The article was received on 07 Sep 2017, accepted on 08 Sep 2017 and first published on 08 Sep 2017


Article type: Paper
DOI: 10.1039/C7OB02245J
Citation: Org. Biomol. Chem., 2017, Advance Article
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    Singlet oxygen-mediated one-pot chemoselective peptide–peptide ligation

    E. Antonatou, Y. Verleysen and A. Madder, Org. Biomol. Chem., 2017, Advance Article , DOI: 10.1039/C7OB02245J

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