A novel azoanthraquinone dye made through innovative enzymatic process

The enzymatic synthesis of an azoanthraquinone by Perenniporia ochroleuca MUCL 41114 laccase was undertaken. The major product was purified and its structure identified by NMR, MS, IR analyses. In order to scale up the production of this azoanthraquinone named Laccase Acid Red 1, a commercial laccase from Trametes versicolor immobilised on perlite as an inexpensive carrier was used. Laccase Acid Red 1 showed lower toxicity than other commercial red dyes, was not mutagenic and displayed low ecotoxicity. In addition, its dyeing properties were assayed on polyamide and the industrial potential of the dye was demonstrated. To our knowledge, this is the first example of sulfonic azoanthraquinone production through enzymatic coupling of aromatic amine monomers. These results show promise for new, safer and environmental friendly routes to azo dye biosynthesis.