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

Author:
ShimodairaPresent address: Institute for Basic Science (IBS), Center for Catalytic Hydrocarbon Functionalizations (CCHF), #5117(E6-4), 291 Deahak-ro, Yuseong-gu, Deajeon, 34141, Republic of Korea., Shingo, Takei, Toshiki, Hojo, Hironobu, Iwaoka, Michio
Source:
Chemical communications 2018 v.54 no.83 pp. 11737-11740
ISSN:
1364-548X
Subject:
chemical reactions, cyclic peptides, glutathione peroxidase, thioesters
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.
Agid:
6169569