Tolnai, Gergely L.Brand, Jonathan P.Waser, Jerome2016-07-192016-07-192016-07-19201610.3762/bjoc.12.74https://infoscience.epfl.ch/handle/20.500.14299/127860WOS:000374468200001The selective functionalization of peptides containing only natural amino acids is important for the modification of biomolecules. In particular, the installation of an alkyne as a useful handle for bioconjugation is highly attractive, but the use of a carbon linker is usually required. Herein, we report the gold-catalyzed direct alkynylation of tryptophan in peptides using the hypervalent iodine reagent TIPS-EBX (1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one). The reaction proceeded in 50-78% yield under mild conditions and could be applied to peptides containing other nucleophilic and aromatic amino acids, such as serine, phenylalanine or tyrosine.alkynesC-H functionalizationgold catalysishypervalent iodinepeptidestext::journal::journal article::research article