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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

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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).

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