Journal
CHEMBIOCHEM
Volume 13, Issue 14, Pages 2094-2099Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.201200407
Keywords
amber suppression; click chemistry; Diels-Alder reaction; protein engineering; unnatural amino acid
Funding
- European Commission [227764]
- Netherlands Organization for Scientific Research (NWO) (VICI grant)
- VCI
- BIF
- Emmy Noether program
- DFG [Transregio83]
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Visualizing biomolecules by fluorescent tagging is a powerful method for studying their behaviour and function inside cells. We prepared and genetically encoded an unnatural amino acid (UAA) that features a bicyclononyne moiety. This UAA offered exceptional reactivity in strain-promoted azidealkyne cycloadditions. Kinetic measurements revealed that the UAA reacted also remarkably fast in the inverse-electron-demand DielsAlder cycloaddition with tetrazine-conjugated dyes. Genetic encoding of the new UAA inside mammalian cells and its subsequent selective labeling at low dye concentrations demonstrate the usefulness of the new amino acid for future imaging studies.
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