A Chemoselective Rapid Azo-Coupling Reaction (CRACR) for Unclickable Bioconjugation.

ABSTRACT: Chemoselective modification of complex biomolecules has become a cornerstone of chemical biology. Despite the exciting developments of the past two decades, the demand for new chemoselective reactions with unique abilities, and those compatible with existing chemistries for concurrent multisite-directed labeling, remains high. Here we show that 5-hydroxyindoles exhibit remarkably high reactivity toward aromatic diazonium ions and this reaction can be used to chemoselectively label proteins. We have previously genetically encoded the noncanonical amino acid 5-hydroxytryptophan in both E. coli and eukaryotes, enabling efficient site-specific incorporation of 5-hydroxyindole into virtually any protein. The 5-hydroxytryptophan residue was shown to allow rapid, chemoselective protein modificati

SUBMITTER: Addy PS 

PROVIDER: S-EPMC5861709 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature