Utility of the Phenacyl Protecting Group in Traceless Protein Semisynthesis through Ligation-Desulfurization Chemistry.

ABSTRACT: Semisynthesis of proteins via expressed protein ligation is a widely applicable method, even more so because of the possibility of ligation at non-cysteine sites using β-mercapto amino acids that can be converted to the corresponding native amino acids by desulfurization. A drawback of this ligation- desulfurization approach is the removal of any unprotected native cysteine residues within the ligated protein segments. Here, we show that the phenacyl (PAc) moiety can be successfully used to protect cysteines within recombinantly generated protein segments. As such, this group was selectively appended onto cysteine side chains within bacterially expressed polypeptides following intein cleavage, which reveals a rather sensitive thioester at the C-terminus. The PAc group proved to be compatib

SUBMITTER: Matveenko M 

PROVIDER: S-EPMC5759462 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature