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Marine Fungi Aspergillus sydowii and Trichoderma sp. Catalyze the Hydrolysis of Benzyl Glycidyl Ether

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Abstract

Whole cells of the marine fungi Aspergillus sydowii Gc12, Penicillium raistrickii Ce16, P. miczynskii Gc5, and Trichoderma sp. Gc1, isolated from marine sponges of the South Atlantic Ocean (Brazil), have been screened for the enzymatic resolution of (±)-2-(benzyloxymethyl)oxirane (benzyl glycidyl ether; 1). Whole cells of A. sydowii Gc12 catalyzed the enzymatic hydrolysis of (R,S)-1 to yield (R)-1 with an enantiomeric excess (ee) of 24–46% and 3-(benzyloxy)propane-1,2-diol (2) with ee values <10%. In contrast, whole cells of Trichoderma sp. Gc1 afforded (S)-1 with ee values up to 60% and yields up to 39%, together with (R)-2 in 25% yield and an ee of 32%. This is the first published example of the hydrolysis of 1 by whole cells of marine fungi isolated from the South Atlantic Ocean. The hydrolases from the two studied fungi exhibited complementary regioselectivity in opening the epoxide ring of racemic 1, with those of A. sydowii Gc12 showing an (S) preference and those of Trichoderma sp. Gc1 presenting an (R) preference for the substrate.

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Acknowledgments

The authors wish to thank Prof. R.G.S. Berlinck (Instituto de Química de São Carlos–USP) for providing the marine fungal strains used in this investigation. The authors gratefully acknowledge the financial support from Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq; grant no. 472663/2004-6 to ALMP) and the Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP; grant no. 2006/54401-2 to ALMP and grant no. 05/60175-2 to RGSB, MHRS, LDS, and EFP). Thanks are also due to Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) and CNPq for grant scholarships to MPM and AMM, respectively.

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Authors and Affiliations

  1. Instituto de Química de São Carlos, Universidade de São Paulo, Av. Trabalhador, São-carlense, 400, CEP 13560-970 CP 780, São Carlos, São Paulo, Brazil

    Mariana Provedel Martins, Ana Maria Mouad, Letícia Boschini & André Luiz Meleiro Porto

  2. Departamento de Ecologia e Biologia Evolutiva, Universidade Federal de São Carlos, Via Washington Luís, Km 235, CEP 13565-905, São Carlos, São Paulo, Brazil

    Mirna Helena Regali Seleghim

  3. Recursos de Divisão Microbianos, Centro Pluridisciplinar de Pesquisas Químicas, Biológicas e Agrícolas, CPQBA, Universidade Estadual de Campinas, Rua Alexandre Casellato, 999, CEP 13140-000, Paulínia, São Paulo, Brazil

    Lara Durães Sette

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  1. Mariana Provedel Martins
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  2. Ana Maria Mouad
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Correspondence to André Luiz Meleiro Porto.

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Martins, M.P., Mouad, A.M., Boschini, L. et al. Marine Fungi Aspergillus sydowii and Trichoderma sp. Catalyze the Hydrolysis of Benzyl Glycidyl Ether. Mar Biotechnol 13, 314–320 (2011). https://doi.org/10.1007/s10126-010-9302-2

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