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Ruthenium‐Catalyzed Azide–Thioalkyne Cycloadditions in Aqueous Media: A Mild, Orthogonal, and Biocompatible Chemical Ligation
Author(s) -
Destito Paolo,
Couceiro José R.,
Faustino Hélio,
López Fernando,
Mascareñas José L.
Publication year - 2017
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.201705006
Subject(s) - bioorthogonal chemistry , ruthenium , chemistry , catalysis , combinatorial chemistry , regioselectivity , aqueous solution , biomolecule , azide , click chemistry , aqueous medium , cycloaddition , organic chemistry , biochemistry
The development of efficient metal‐promoted bioorthogonal ligations remains as a major scientific challenge. Demonstrated herein is that azides undergo efficient and regioselective room‐temperature annulations with thioalkynes in aqueous milieu when treated with catalytic amounts of a suitable ruthenium complex. The reaction is compatible with different biomolecules, and can be carried out in complex aqueous mixtures such as phosphate buffered saline, cell lysates, fetal bovine serum, and even living bacteria (E. coli). Importantly, the reaction is mutually compatible with the classical CuAAC.