Amino Acids for Diels–Alder Reactions in Living Cells

Tilman Plass(European Molecular Biology Laboratory), Sigrid Milles(European Molecular Biology Laboratory), Christine Koehler(European Molecular Biology Laboratory), Jędrzej Szymański(European Molecular Biology Laboratory), Rainer Mueller(European Molecular Biology Laboratory), Manfred Wießler(DKFZ-ZMBH Alliance), Carsten Schultz(European Molecular Biology Laboratory), Edward A. Lemke(European Molecular Biology Laboratory)
Angewandte Chemie International Edition
March 30, 2012
Cited by 338

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). Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.


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