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Propargyl Amides as Irreversible Inhibitors of Cysteine Proteases—A Lesson on the Biological Reactivity of Alkynes
Author(s) -
Arkona Christoph,
Rademann Jörg
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201303544
Subject(s) - proteases , reactivity (psychology) , propargyl , cysteine , bioorthogonal chemistry , chemistry , amide , combinatorial chemistry , biochemistry , enzyme , click chemistry , catalysis , medicine , alternative medicine , pathology
Are aliphatic alkynes truly bioorthogonal? In an attempt to prepare clickable ubiquitin derivatives bearing a C‐terminal propargyl amide, two groups have now independently discovered propargylamides to be irreversible inhibitors of cysteine proteases. The unexpected findings demonstrate the unexpected reactivity of alkynes in protein‐templated reactions and introduce a novel class of activity‐based protein probes.