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Synthesis of thioester peptides for the incorporation of thioamides into proteins by native chemical ligation.

ABSTRACT: Thioamides can be used as photoswitches, as reporters of local environment, as inhibitors of enzymes, and as fluorescence quenchers. We have recently demonstrated the incorporation of thioamides into polypeptides and proteins using native chemical ligation (NCL). In this protocol, we describe procedures for the synthesis of a thioamide precursor and an NCL-ready thioamide-containing peptide using Dawson's N-acyl-benzimidazolinone (Nbz) process. We include a description of the synthesis by NCL of a thioamide-labeled fragment of the neuronal protein α-synuclein.

SUBMITTER: Batjargal S 

PROVIDER: S-EPMC4199922 | biostudies-literature | 2014 Feb

REPOSITORIES: biostudies-literature

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Synthesis of thioester peptides for the incorporation of thioamides into proteins by native chemical ligation.

Batjargal Solongo S   Huang Yun Y   Wang Yanxin J YJ   Petersson E James EJ  

Journal of peptide science : an official publication of the European Peptide Society 20140109 2

Thioamides can be used as photoswitches, as reporters of local environment, as inhibitors of enzymes, and as fluorescence quenchers. We have recently demonstrated the incorporation of thioamides into polypeptides and proteins using native chemical ligation (NCL). In this protocol, we describe procedures for the synthesis of a thioamide precursor and an NCL-ready thioamide-containing peptide using Dawson's N-acyl-benzimidazolinone (Nbz) process. We include a description of the synthesis by NCL of  ...[more]