Genetically Encoded Copper‐Free Click Chemistry

Plass, Tilman; Milles, Sigrid; Koehler, Christine; Schultz, Carsten; Lemke, Edward A.

doi:10.1002/anie.201008178

Cited by 289 publications

(242 citation statements)

References 42 publications

(31 reference statements)

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“…6) were incorporated by amber (TAG) stop-codon suppression according to the expanded genetic code concept 38 . We used the previously reported tRNA Pyl /PylRS AF pair and GFP 39TAG (TAG codon in position 39) in our study to express GFP TAG UAA and so genetically encode the respective UAAs 36,39 . The TCO derivative permits fast labelling of probes that carry tetrazines, whereas the SCO derivative serves as a control.…”

Section: Resultsmentioning

confidence: 99%

A near-infrared fluorophore for live-cell super-resolution microscopy of cellular proteins

et al. 2013

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The ideal fluorescent probe for bioimaging is bright, absorbs at long wavelengths and can be implemented flexibly in living cells and in vivo. However, the design of synthetic fluorophores that combine all of these properties has proved to be extremely difficult. Here, we introduce a biocompatible near-infrared silicon-rhodamine probe that can be coupled specifically to proteins using different labelling techniques. Importantly, its high permeability and fluorogenic character permit the imaging of proteins in living cells and tissues, and its brightness and photostability make it ideally suited for live-cell super-resolution microscopy. The excellent spectroscopic properties of the probe combined with its ease of use in live-cell applications make it a powerful new tool for bioimaging.

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Section: Resultsmentioning

confidence: 99%

A near-infrared fluorophore for live-cell super-resolution microscopy of cellular proteins

et al. 2013

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“…4a). The site-specific incorporation of cyclooctynes 97 and biscyclononynes 98 into proteins by amberstop codon suppression has also recently been reported. However, limitations remain, such as occasional difficulty in the synthesis and handling of strained and unstable compounds, while crucially a degree of incompatibility towards cysteine has been reported 99,100 .…”

Section: Review Nature Communications | Doi: 101038/ncomms5740mentioning

confidence: 95%

Selective chemical protein modification

2014

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“…demonstrated that 3-azido-7-hydroxycoumarin can also be incorporated into proteins site-specifically via metal-free click chemistry using an unnatural ring-strained-conjugated lysine amino acid based on cyclooctyne. 77,78 To accomplish this, they employed a pyrrolysine Methanosarcina bakeri/mazei tRNA/pylRS pair evolved by Chin and coworkers. 79 Lemke evolved the pair to accommodate the extra bulk of the cyclooctyne amino acid and used it to incorporate the cyclooctyne moiety into the mCherry protein ( Figure 9).…”

Section: Flaas Employed In Fret Experimentsmentioning

confidence: 99%