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Issue 83, 2018
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Synthesis of selenocysteine-containing cyclic peptides via tandem N-to-S acyl migration and intramolecular selenocysteine-mediated native chemical ligation

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Abstract

Selenocysteine-containing cyclic 8-mer peptides, which were designed to mimic the plausible catalytic tetrad of glutathione peroxidase, were successfully synthesized in one pot via tandem N-to-S acyl migration of N-alkylcysteine (NAC)-containing selenopeptides and intramolecular selenocysteine-mediated native chemical ligation (Sec-NCL) of the generated thioesters.

Graphical abstract: Synthesis of selenocysteine-containing cyclic peptides via tandem N-to-S acyl migration and intramolecular selenocysteine-mediated native chemical ligation

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Article information


Submitted
22 Aug 2018
Accepted
24 Sep 2018
First published
25 Sep 2018

Chem. Commun., 2018,54, 11737-11740
Article type
Communication

Synthesis of selenocysteine-containing cyclic peptides via tandem N-to-S acyl migration and intramolecular selenocysteine-mediated native chemical ligation

S. Shimodaira, T. Takei, H. Hojo and M. Iwaoka, Chem. Commun., 2018, 54, 11737
DOI: 10.1039/C8CC06805D

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