Amino acids for diels-alder reactions in living cells

Tilman Plass, Sigrid Milles, Christine Koehler, Jȩdrzej Szymański, Rainer Mueller, Manfred Wießler, Carsten Schultz, Edward A. Lemke

Research output: Contribution to journalArticlepeer-review

229 Scopus citations

Abstract

Under tension: A set of genetically encoded unnatural amino acids can be used for biocompatible site-specific labeling of proteins with fluorogenic dyes. The new compounds have norbornene and trans-cyclooctene units that react with tetrazine derivatives in an inverse-electron-demand Diels-Alder cycloaddition (left in picture). The technique offers fast labeling that is orthogonal to labeling through azide-cyclooctyne click reaction (right).

Original languageEnglish (US)
Pages (from-to)4166-4170
Number of pages5
JournalAngewandte Chemie - International Edition
Volume51
Issue number17
DOIs
StatePublished - Apr 23 2012

Keywords

  • Diels-Alder reactions
  • amber suppression
  • click chemistry
  • protein engineering
  • unnatural amino acids

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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