Protein Modification by Strain-Promoted Alkyne–Nitrone Cycloaddition (pages 3065–3068)
Xinghai Ning, Rinske P. Temming, Jan Dommerholt, Jun Guo, Daniel B. Ania, Marjoke F. Debets, Margreet A. Wolfert, Geert-Jan Boons and Floris L. van Delft
Version of Record online: 23 MAR 2010 | DOI: 10.1002/anie.201000408
Quicker and slicker: An efficient metal-free 1,3-dipolar cycloaddition of dibenzocyclooctynes with nitrones proceeded with rate constants of up to 39 M−1 s−1, or up to 300 times faster than similar reactions with azides. This strategy is useful for the site-specific N-terminal modification of peptides and proteins (see scheme).