PUBLICATION

Catalytic Azide Reduction in Biological Environments

Authors
Sasmal, P.K., Carregal-Romero, S., Han, A.A., Streu, C.N., Lin, Z., Namikawa, K., Elliott, S.L., Köster, R.W., Parak, W.J., and Meggers, E.
ID
ZDB-PUB-120424-8
Date
2012
Source
Chembiochem : a European journal of chemical biology   13(8): 1116-1120 (Journal)
Registered Authors
Köster, Reinhard W., Namikawa, Kazuhiko
Keywords
azide reductions, catalysis, cellular chemistry, fluorescence, iron porphyrins
MeSH Terms
  • Amines/chemistry
  • Animals
  • Azides/chemistry*
  • Caenorhabditis elegans
  • Catalysis
  • Environment
  • Ferric Compounds/chemistry*
  • HeLa Cells
  • Humans
  • Metalloporphyrins/chemistry*
  • Oxidation-Reduction
  • Zebrafish
PubMed
22514188 Full text @ Chembiochem
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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