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Phenolic Compound Biotransformation by Trametes versicolor ATCC 200801 and Molecular Docking Studies

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Abstract

The filamentous fungus Trametes versicolor is a rich source of laccase (Tvlac). Laccases catalyze reactions that convert substituted phenol substrates into diverse derivatives through aromatic oxidation. We investigated methyl p-coumarate, methyl ferulate, and methyl caffeate biotransformation by Trametes versicolor ATCC 200801. Despite substrate similarity, the biotransformation reactions varied widely. Only methyl p-coumarate was converted into three derivatives. We isolated and identified the chemical structures of such derivatives by NMR and IR analysis. Hydroxylation, methylation, and hydrolysis were the main reactions resulting from the studied biotransformation. We also analyzed the interactions between Tvlac (PDB ID: 1GYC) and the three phenolic substrates by molecular docking simulations. The substituents in the phenol ring influenced substrate conformation and orientation in the Tvlac site. The biotransformation reaction selectivity correlated with the different binding energies to the Tvlac site. Our results demonstrated that docking studies successfully predict the biotransformation of cinnamic acid analogs by T. versicolor.

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Acknowledgments

JCSC thanks FAPESB for his scholarship.

Funding

This work was supported by the Brazilian National Council for Scientific and Technological Development (CNPq), Brazilian Coordination for Improvement of Personnel Higher Education (CAPES), and Bahia Research Foundation (FAPESB, grant numbers JCB-0039/2013 and RED-008/2013).

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Authors and Affiliations

  1. Departamento de Química Orgânica, Instituto de Química, Universidade Federal da Bahia, Barão de Jeremoabo, Salvador, BA, 40170-115, Brazil

    João Carlos Silva Conceição & Eliane de Oliveira Silva

  2. Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP, Brazil

    Herbert Júnior Dias & Antônio Eduardo Miller Crotti

  3. Laboratório de Bioinformática e Modelagem Molecular (LaBiMM), Departamento do Medicamento, Faculdade de Farmácia, Universidade Federal da Bahia, Salvador, BA, Brazil

    Clarissa Maria Souza Peralva & Samuel Silva da Rocha Pita

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  1. João Carlos Silva Conceição
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Correspondence to Eliane de Oliveira Silva.

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Conceição, J.C.S., Dias, H.J., Peralva, C.M.S. et al. Phenolic Compound Biotransformation by Trametes versicolor ATCC 200801 and Molecular Docking Studies. Appl Biochem Biotechnol 190, 1498–1511 (2020). https://doi.org/10.1007/s12010-019-03191-y

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