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Biotransformation of (E)-2-Methyl-3-Phenylacrylaldehyde Using Mycelia of Penicillium citrinum CBMAI 1186, Both Free and Immobilized on Chitosan

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Abstract

This study applied the use of marine-derived fungus Penicillium citrinum CBMAI 1186 in the stereoselective reduction of the C=C double bond of the prochiral (E)-2-methyl-3-phenylacrylaldehyde 1. The fungus immobilized on chitosan, obtained by multistep ultrasound-assisted deacetylation process (Ch-USAD), produced the (S)-(+)-2-methyl-3-phenylpropan-1-ol 3 (c = 49%, 40% ee) isomer and (±)-2-methyl-3-phenylacrilic acid 4 (c = 35%); in contrast, immobilized mycelia on commercial chitosan (Ch-C) yielded the (S)-(+)-2-methyl-3-phenylpropan-1-ol 3 (c = 48%, 10% ee) and (±)-2-methyl-3-phenylpropanal 1a (c = 41%). The reaction using free mycelia gave a 40% yield of (S)-(+)-2-methyl-3-phenylpropan-1-ol 3 with 10% ee. These results showed that the crystallinity form and molecular weight of chitosan (Ch-C or Ch-USAD) used to immobilized mycelia of P. citrinum CBMAI 1186 influenced in the biotransformation of (E)-2-methyl-3-phenylacrylaldehyde 1. Therefore, marine-derived fungus P. citrinum CBMAI 1186 immobilized on chitosan can be a potential alternative in the studies of hydrogenation of the α,β-unsaturated carbon-carbon (α,β-C=C) double bond.

Marine-derived fungus Penicillium citrinum CBMAI 1186 immobilized on chitosan in the stereoselective reduction of the C=C double bond of the prochiral (E)-2-methyl-3-phenylacrylaldehyde

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Funding

Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq, Proc. N0. 302528/2017-2) and Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP, Proc. N0. 2014/18257-0 and Proc. N0. 2016/20155-7) provided financial support. The Center for Research on Science and Technology of BioResources of the University of São Paulo also provided financial and structural support.

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  1. Laboratório de Biocatálise e Síntese Orgânica Aplicada, Departamento de Ciências Exatas, Universidade Federal do Amapá, Rod. JK KM 02, Macapa, Amapá, 68902-280, Brazil

    Irlon M. Ferreira

  2. Instituto de Química de São Carlos, Universidade de São Paulo, Av. Trabalhador São-Carlense, 400,, Sao Carlos, São Paulo, 13566-590, Brazil

    Irlon M. Ferreira, Anderson Fiamingo & Sergio P. Campana-Filho

  3. Laboratório de Química Orgânica e Biocatálise, Instituto de Química de São Carlos, Universidade de São Paulo, Av. João Dagnone, 1100, Ed. Química Ambiental, J. Santa Angelina,, Sao Carlos, São Paulo, 13563-120, Brazil

    André L. M. Porto

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  1. Irlon M. Ferreira
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  2. Anderson Fiamingo
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  3. Sergio P. Campana-Filho
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  4. André L. M. Porto
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Correspondence to Irlon M. Ferreira or André L. M. Porto.

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Ferreira, I.M., Fiamingo, A., Campana-Filho, S.P. et al. Biotransformation of (E)-2-Methyl-3-Phenylacrylaldehyde Using Mycelia of Penicillium citrinum CBMAI 1186, Both Free and Immobilized on Chitosan. Mar Biotechnol 22, 348–356 (2020). https://doi.org/10.1007/s10126-020-09954-7

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