4 years ago

One-pot four-segment ligation realized by selenoester and its application to the synthesis of superoxide dismutase

Toshiki Takei, Hironobu Hojo, Tomoshige Andoh, Toshifumi Takao
The synthesis of the peptide selenoester was efficiently carried out by the 9-fluorenylmethoxycarbonyl method using the N-alkylcysteine at the C-terminus of the peptide as the N-to-S acyl shift device. The selenoester highly selectively reacted with the terminal amino group of the peptide aryl thioester in the presence of N, N-diisopropylethylamine and dipyridyldisulfide, maintaining the aryl thioester intact. Combining with the silver ion promoted and silver ion free thioester activation method, the one-pot four-segment ligation was realized. The method was successfully used to assemble the entire sequence of the superoxide dismutase (SOD) composed of 153 amino acid residues in one-pot. After the folding reaction, the fully-active SOD was obtained.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201709418

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