Frontispiece: Chemo‐ and Regioselective Ethynylation of Tryptophan‐Containing Peptides and Proteins. Issue 5 (20th January 2016)

• Record Type: Journal Article
• Authors: Hansen, Morten Borre; Hubálek, František; Skrydstrup, Troels; Hoeg‐Jensen, Thomas
• Is Part Of: Chemistry. Volume 22:Issue 5(2016)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2016-01-20
• Subjects: alkynylation -- C−H activation -- chemoselectivity -- gold -- peptides; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201680561
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract : A gold Tr(i)p ! In their Communication onpage 1572 ff., M. B. Hansen and co‐workers functionalized (poly)‐peptides with TIPS‐ethynyl moieties at their tryptophan residues using Waser's reagent, 1‐[(triisopropylsilyl)ethynyl]‐1, 2‐benziodoxol‐3(1 H )‐one (TIPS‐EBX), under gold(I) catalysis. The reaction proceeded in a regio‐ and chemoselective manner leading to C2 substitution at the tryptophan residues only. Subsequently, the terminal alkyne was used to label one of the model peptides with a fluorophore by means of copper‐catalyzed click chemistry.