Genetically encoded 1,2-aminothiols facilitate rapid and site-specific protein labeling via a bio-orthogonal cyanobenzothiazole condensation

Duy P. Nguyen, Thomas Elliott, Matthew Holt, Tom W. Muir, Jason W. Chin

Research output: Contribution to journalArticle

110 Scopus citations

Abstract

We report evolved orthogonal pyrrolysyl-tRNA synthetase/tRNA CUA pairs that direct the efficient, site-specific incorporation of N ε-l-thiaprolyl-l-lysine, N ε-d-cysteinyl-l- lysine, and N ε-l-cysteinyl-l-lysine into recombinant proteins in Escherichia coli. We demonstrate that the unique 1,2-aminothiol introduced by our approach can be efficiently, rapidly, and specifically labeled via a cyanobenzothiazole condensation to quantitatively introduce biophysical probes into proteins. Moreover, we show that, in combination with cysteine labeling, this approach allows the dual labeling of proteins with distinct probes at two distinct, genetically defined sites.

Original languageEnglish (US)
Pages (from-to)11418-11421
Number of pages4
JournalJournal of the American Chemical Society
Volume133
Issue number30
DOIs
StatePublished - Aug 3 2011
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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