Frontispiece: Chemo‐ and Regioselective Ethynylation of Tryptophan‐Containing Peptides and Proteins | Zendy

Hansen Morten Borre | Zendy; Hubálek František | Zendy; Skrydstrup Troels | Zendy; HoegJensen Thomas | Zendy

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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.

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