Catalytic azide reduction in biological environments |
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Authors: | Sasmal Pijus K Carregal-Romero Susana Han Alice A Streu Craig N Lin Zhijie Namikawa Kazuhiko Elliott Samantha L Köster Reinhard W Parak Wolfgang J Meggers Eric |
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Affiliation: | 1. Fachbereich Chemie, Philipps‐Universit?t Marburg, Hans‐Meerwein‐Strasse, 35043 Marburg (Germany);2. Fachbereich Physik and WZMW, Philipps‐Universit?t Marburg, Renthof 7, 35037 Marburg (Germany);3. Department of Chemistry and Biochemistry, St. Mary's College of Maryland, St. Mary's City, MD 20686 (USA);4. Zoologisches Institut, Technische Universit?t Braunschweig, Spielmannstrasse 8, 38106 Braunschweig (Germany);5. Department of Biology, St. Mary's College of Maryland, St. Mary's City, MD 20686 (USA) |
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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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Keywords: | azide reductions catalysis cellular chemistry fluorescence iron porphyrins |
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