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

Author(s)

Ferreira, Irlon M. ^{[1, 2]} ; Fiamingo, Anderson ^[1] ; Campana-Filho, Sergio P. ^[1] ; Porto, Andre L. M. ^[3]

Affiliation

^[1] Univ Sao Paulo, Inst Quim Sao Carlos, Av Trabalhador Sao Carlense 400, BR-13566590 Sao Carlos, SP - Brazil

^[2] Univ Fed Amapa, Dept Ciencias Exatas, Lab Biocatalise & Sintese Organ Aplicada, Rod JK KM 02, BR-68902280 Macapa, Amapa - Brazil

^[3] Univ Sao Paulo, Inst Quim Sao Carlos, Lab Quim Organ & Biocatalise, Av Joao Dagnone 1100, Ed Quim Ambiental, BR-13563120 Sao Carlos, SP - Brazil

• Document type: Journal article
• Source: MARINE BIOTECHNOLOGY; v. 22, n. 3 FEB 2020.
• Web of Science Citations: 0

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 alpha,beta-unsaturated carbon-carbon (alpha,beta-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 (AU)

• FAPESP's process: 14/18257-0 - New approaches in biocatalytic reactions
• Grantee: Andre Luiz Meleiro Porto
• Support Opportunities: Regular Research Grants
• FAPESP's process: 16/20155-7 - Biocatalytic reactions of aminolysis and kinetic resolution by lipases and biodegradation of agrochemicals by microorganisms
• Grantee: Andre Luiz Meleiro Porto
• Support Opportunities: Regular Research Grants