Amino Acids for Diels–Alder Reactions in Living Cells

Authors

  • Tilman Plass,

    1. Structural and Computational Biology Unit and Cell Biology and Biophysics Unit, EMBL, Meyerhofstrasse 1, 69117 Heidelberg (Germany)
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  • Sigrid Milles,

    1. Structural and Computational Biology Unit and Cell Biology and Biophysics Unit, EMBL, Meyerhofstrasse 1, 69117 Heidelberg (Germany)
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  • Christine Koehler,

    1. Structural and Computational Biology Unit and Cell Biology and Biophysics Unit, EMBL, Meyerhofstrasse 1, 69117 Heidelberg (Germany)
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  • Dr. Jędrzej Szymański,

    1. Structural and Computational Biology Unit and Cell Biology and Biophysics Unit, EMBL, Meyerhofstrasse 1, 69117 Heidelberg (Germany)
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  • Dr. Rainer Mueller,

    1. Structural and Computational Biology Unit and Cell Biology and Biophysics Unit, EMBL, Meyerhofstrasse 1, 69117 Heidelberg (Germany)
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  • Prof. Dr. Manfred Wießler,

    1. Biological Chemistry, DKFZ, Im Neuenheimer Feld 280, 69120 Heidelberg (Germany)
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  • Priv.-Doz. Dr. Carsten Schultz,

    Corresponding author
    1. Structural and Computational Biology Unit and Cell Biology and Biophysics Unit, EMBL, Meyerhofstrasse 1, 69117 Heidelberg (Germany)
    • Structural and Computational Biology Unit and Cell Biology and Biophysics Unit, EMBL, Meyerhofstrasse 1, 69117 Heidelberg (Germany)
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  • Dr. Edward A. Lemke

    Corresponding author
    1. Structural and Computational Biology Unit and Cell Biology and Biophysics Unit, EMBL, Meyerhofstrasse 1, 69117 Heidelberg (Germany)
    • Structural and Computational Biology Unit and Cell Biology and Biophysics Unit, EMBL, Meyerhofstrasse 1, 69117 Heidelberg (Germany)
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  • We thank P. G. Schultz for a mammalian RS expression plasmid, V. VanDelinder, and A. Ori for helpful discussions. This study was technically supported by the EMBL-ALMF, -PEPCF, and -PCF core facilities. T.P. is a VCI, S.M. a BIF, and J.S. an EMBO fellow. E.A.L. acknowledges funding by the Emmy Noether program and C.S. from Transregio83 of the DFG.

Abstract

original image

Unter Spannung: Eine Reihe genetisch codierter nichtnatürlicher Aminosäuren kann für die biokompatible ortsspezifische Markierung von Proteinen mit fluorogenen Farbstoffen verwendet werden. Die neuen Verbindungen haben Norbornen- und trans-Cycloocten-Einheiten, die mit Tetrazinen in einer Diels-Alder-Cycloaddition mit inversem Elektronenbedarf reagieren (links im Bild). Diese schnelle Markierungsreaktion ist orthogonal zur Azid-Cyclooctin-Klick-Reaktion (rechts).

Ancillary