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Frontispiece: Chemo‐ and Regioselective Ethynylation of Tryptophan‐Containing Peptides and Proteins
Author(s) -
Hansen Morten Borre,
Hubálek František,
Skrydstrup Troels,
HoegJensen Thomas
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201680561
Subject(s) - tryptophan , fluorophore , regioselectivity , alkyne , chemistry , reagent , combinatorial chemistry , click chemistry , stereochemistry , catalysis , organic chemistry , amino acid , biochemistry , fluorescence , quantum mechanics , physics
A gold Tr(i)p ! In their Communication on page 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.