Journal
CHEMBIOCHEM
Volume 13, Issue 8, Pages 1116-1120Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cbic.201100719
Keywords
azide reductions; catalysis; cellular chemistry; fluorescence; iron porphyrins
Funding
- Philipps-University Marburg (Germany)
- China Scholarship Council
- Junta Andalucia (Spain)
- German Research Foundation [FOR630, ME-1805/3-1, SPP1313, PA794/4-1, KO1949/4-1]
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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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