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Catalytic Azide Reduction in Biological Environments
Author(s) -
Sasmal Pijus K.,
CarregalRomero Susana,
Han Alice A.,
Streu Craig N.,
Lin Zhijie,
Namikawa Kazuhiko,
Elliott Samantha L.,
Köster Reinhard W.,
Parak Wolfgang J.,
Meggers Eric
Publication year - 2012
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201100719
Subject(s) - azide , danio , chemistry , catalysis , combinatorial chemistry , reducing agent , caenorhabditis elegans , zebrafish , chemical biology , fluorophore , oxidation reduction , biochemistry , organic chemistry , fluorescence , physics , quantum mechanics , gene
In the quest for the identification of catalytic transformations to be used in chemical biology and medicinal chemistry, we identified iron(III) meso ‐tetraarylporphines as efficient catalysts for the reduction of aromatic azides to their amines. The reaction uses thiols as reducing agents and tolerates water, air, and other biological components. A caged fluorophore was employed to demonstrate that the reduction can be performed even in living mammalian cells. However, in vivo experiments in nematodes ( Caenorhabditis elegans ) and zebrafish ( Danio rerio ) revealed a limitation to this method: the metabolic reduction of aromatic azides.