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Issue 38, 2017
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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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Supplementary files

Article information


Submitted
07 Sep 2017
Accepted
08 Sep 2017
First published
08 Sep 2017

Org. Biomol. Chem., 2017,15, 8140-8144
Article type
Paper

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

E. Antonatou, Y. Verleysen and A. Madder, Org. Biomol. Chem., 2017, 15, 8140
DOI: 10.1039/C7OB02245J

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