Synthesis and structural characterization of a novel phenoxazinone dye by use of a fungal laccase

Forte, Stefania;Polak, Jolanta;Valensin, Daniela;Taddei, Maurizio;Pogni, Rebecca;et.al.
(2010) Journal of Molecular Catalysis B: Enzymatic — Vol. 63, n° 3-4, p. 116-120 (2010)

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  • Forte, StefaniaDepartment of Chemistry, University of Siena, Via A. De Gasperi, 53100 Siena, Italy
    Author
  • Polak, JolantaDepartment of Biochemistry, Maria Curie-Sklodowska University, Lublin, Poland
    Author
  • Valensin, DanielaDepartment of Chemistry, University of Siena, Via A. De Gasperi, 53100 Siena, Italy
    Author
  • Taddei, MaurizioDepartment of Pharmaceutical Chemistry, University of Siena, Siena, Italy
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  • Vanhulle, SophieUCLouvain
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  • Pogni, RebeccaDepartment of Chemistry, University of Siena, Via A. De Gasperi, 53100 Siena, Italy
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Abstract
Laccase, isolated from Cerrena unicolor, is able to transform 3-amino-4-hydroxybenzensulfonic acid into a water soluble phenoxazine dye with an extinction coefficient (epsilon) of 8600 M-1 cm(-1). The dye has been characterized using a variety of different analytic and spectroscopic techniques like UV-vis spectroscopy, HPLC (High Performance Liquid Chromatography), ESI/MS (Electrospray Ionization Mass Spectrometry) and the following NMR experiments: H-1, C-13, TOCSY (Total Correlation Spectroscopy), HSQC (Heteronuclear Single Quantum Coherence). HMBC (Heteronuclear Multiple Bond Coherence) showing the structure of 2-amino-3-oxo-3H-phenoxazine-8-sulfonic acid. The advantages of the presented biocatalytic system, in alignment with chemical system to obtain Curie_22, are eco-sustainability and one step performance. (C) 2010 Elsevier B.V. All rights reserved.
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Forte, S., Polak, J., Valensin, D., Taddei, M., Basosi, R., Vanhulle, S., Jarosz-Wilkolazka, A., & Pogni, R. (2010). Synthesis and structural characterization of a novel phenoxazinone dye by use of a fungal laccase. Journal of Molecular Catalysis B: Enzymatic, 63(3-4), 116-120. https://doi.org/10.1016/j.molcatb.2009.12.018 (Original work published 2010)