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

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

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-media...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2018-10, Vol.54 (83), p.11737-11740
Hauptverfasser: Shimodaira, Shingo, Takei, Toshiki, Hojo, Hironobu, Iwaoka, Michio
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Chemical synthesis
Glutathione
Migration
Organic chemistry
Peptides
Peroxidase
Thioesters
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Zusammenfassung: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc06805d