Catalytic Azide Reduction in Biological Environments
ChemBioChem2012Vol. 13(8), pp. 1116–1120
Citations Over TimeTop 10% of 2012 papers
Pijus K. Sasmal, Susana Carregal‐Romero, Alice A. Han, Craig Streu, Zhijie Lin, Kazuhiko Namikawa, Samantha Elliott, Reinhard W. Köster, Wolfgang J. Parak, Eric Meggers
Abstract
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.
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