Frontispiece: Highly Stable trans‐Cyclooctene Amino Acids for Live‐Cell Labeling. Issue 35 (18th August 2015)

• Record Type: Journal Article
• Authors: Hoffmann, Jan‐Erik; Plass, Tilman; Nikić, Ivana; Aramburu, Iker Valle; Koehler, Christine; Gillandt, Hartmut; Lemke, Edward A.; Schultz, Carsten
• Is Part Of: Chemistry. Volume 21:Issue 35(2015)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2015-08-18
• Subjects: amino acids -- cell labeling -- organic synthesis -- proteins -- receptors; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201583561
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract : Amino Acids for Live‐Cell Labeling . The non‐canonical amino acid trans ‐cyclooctene‐lysine (TCO*) allows the rapid and specific labeling of proteins by click chemistry. In their Communication onpage 12266 ff., C. Schultz et al. present a novel synthesis route for TCO* and investigate the stability and reactivity of the isomers, as well as their utility for live‐cell labeling. The reactivity of TCO* conformers with tetrazines in comparison to other common click reactions is systematically quantified by using density functional calculations. The axial isomer of TCO* incorporated in a green fluorescent protein reacts with a tetrazine attached to Cy5. The relevant orbitals involved in this extremely fast click reaction are shown on a background of mammalian cells expressing insulin receptors selectively labeled by this method.