Synthesis of Substituted 4-Arylamino-1,2-naphthoquinones in One-Pot Reactions Using CotA-Laccase as Biocatalyst

Ana Catarina Sousa, Iolanda Santos, M. F.M.M. Piedade, Lígia O. Martins, M. Paula Robalo

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1 Citation (Scopus)

Abstract

An efficient and environmentally benign biocatalytic strategy for the synthesis of substituted 4-arylamino-1,2-naphthoquinones was developed, through a cross-coupling reaction in which the 1,2-naphthoquinone nucleus, formed in the biocatalytic process mediated by CotA-laccase from Bacillus subtilis, is the key synthetic intermediate. Electrochemical data and kinetic parameters were determined revealing a significant higher specificity of CotA-laccase for 4-amino-3-hydroxynaphthalene-1-sulfonic acid (AHNSA). This ability of CotA-laccase to discriminate between oxidisable aromatic amines allows the set-up of one-pot reactions in the presence of the enzyme, between AHNSA and a set of appropriate aromatic amines under mild reaction conditions. (Figure presented.).

Original languageEnglish
Pages (from-to)3380-3387
Number of pages8
JournalAdvanced Synthesis and Catalysis
Volume362
Issue number16
DOIs
Publication statusPublished - 19 Aug 2020

Keywords

  • 4-arylamino-1,2-naphthoquinones
  • biocatalysis
  • CotA-laccase
  • green synthesis

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