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<p>Baeyer-Villiger monooxygenases (BVMOs) are versatile biocatalysts that catalyse the oxidation of ketones to esters with high regio- and enantioselectivity, operating under mild reaction conditions while reducing hazardous waste. Some BVMOs can convert cellulose-derived alkyl levulinates to 3-acetoxypropionates (3-APs), which are key intermediates in the production of 3-hydroxypropionic acid (3-HP), a versatile building block chemical. In this study, a BVMO from <i>Acinetobacter radioresistens</i> (<i>Ar</i>-BVMO) was tested as a biocatalyst for the conversion of three marketed alkyl levulinates: methyl, ethyl and butyl levulinate. The enzyme showed 4-fold higher catalytic efficiency (k<sub>cat</sub>/K<sub>M</sub>) and enhanced regioselectivity for the desired 3-AP product (4:1 ratio) when using butyl levulinate as a substrate. <i>Escherichia coli</i> whole-cells over-expressing <i>Ar</i>-BVMO were exploited to increase the product yield, achieving 85% conversion in 9&#xa0;h. To further improve the sustainability of this biotransformation, butyl levulinate was obtained via microwave-assisted alcoholysis of pulp, a renewable cellulose feedstock, achieving 92.7% selectivity. Despite challenges posed by poor solubility of the resulting mixture in aqueous environment, <i>Ar</i>-BVMO in cell lysates was able to fully convert butyl levulinate within 24&#xa0;h, efficiently producing 3-HP precursors without additional purification steps. These findings highlight the feasibility of this chemoenzymatic approach to convert cellulose-based raw materials to platform chemicals.</p>

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Biocatalytic production of 3-hydroxypropionic acid precursors using a regioselective Baeyer-Villiger monooxygenase

  • 期刊论文

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  • 发表日期：

    2025年4月22日

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  • Melissa De Angelis,
  • Danilo Correddu,
  • Fabio Bucciol,
  • Silvia Tabasso,
  • Gianluca Catucci,
  • Giancarlo Cravotto,
  • Carlo Roggero,
  • Gianfranco Gilardi,
  • Sheila J. Sadeghi

摘要

Baeyer-Villiger monooxygenases (BVMOs) are versatile biocatalysts that catalyse the oxidation of ketones to esters with high regio- and enantioselectivity, operating under mild reaction conditions while reducing hazardous waste. Some BVMOs can convert cellulose-derived alkyl levulinates to 3-acetoxypropionates (3-APs), which are key intermediates in the production of 3-hydroxypropionic acid (3-HP), a versatile building block chemical. In this study, a BVMO from Acinetobacter radioresistens (Ar-BVMO) was tested as a biocatalyst for the conversion of three marketed alkyl levulinates: methyl, ethyl and butyl levulinate. The enzyme showed 4-fold higher catalytic efficiency (kcat/KM) and enhanced regioselectivity for the desired 3-AP product (4:1 ratio) when using butyl levulinate as a substrate. Escherichia coli whole-cells over-expressing Ar-BVMO were exploited to increase the product yield, achieving 85% conversion in 9 h. To further improve the sustainability of this biotransformation, butyl levulinate was obtained via microwave-assisted alcoholysis of pulp, a renewable cellulose feedstock, achieving 92.7% selectivity. Despite challenges posed by poor solubility of the resulting mixture in aqueous environment, Ar-BVMO in cell lysates was able to fully convert butyl levulinate within 24 h, efficiently producing 3-HP precursors without additional purification steps. These findings highlight the feasibility of this chemoenzymatic approach to convert cellulose-based raw materials to platform chemicals.