Structure- and computational-aided engineering of an oxidase to produce isoeugenol from a lignin-derived compound

Yiming Guo, Laura Alvigini, Milos Trajkovic, Lur Alonso-Cotchico, Emanuele Monza, Simone Savino, Ivana Marić, Andrea Mattevi and Marco W. Fraaije ()
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Yiming Guo: University of Groningen
Laura Alvigini: University of Pavia
Milos Trajkovic: University of Groningen
Lur Alonso-Cotchico: Zymvol Biomodeling S.L.
Emanuele Monza: Zymvol Biomodeling S.L.
Simone Savino: University of Groningen
Ivana Marić: University of Groningen
Andrea Mattevi: University of Pavia
Marco W. Fraaije: University of Groningen

Nature Communications, 2022, vol. 13, issue 1, 1-12

Abstract: Abstract Various 4-alkylphenols can be easily obtained through reductive catalytic fractionation of lignocellulosic biomass. Selective dehydrogenation of 4-n-propylguaiacol results in the formation of isoeugenol, a valuable flavor and fragrance molecule and versatile precursor compound. Here we present the engineering of a bacterial eugenol oxidase to catalyze this reaction. Five mutations, identified from computational predictions, are first introduced to render the enzyme more thermostable. Other mutations are then added and analyzed to enhance chemoselectivity and activity. Structural insight demonstrates that the slow catalytic activity of an otherwise promising enzyme variant is due the formation of a slowly-decaying covalent substrate-flavin cofactor adduct that can be remedied by targeted residue changes. The final engineered variant comprises eight mutations, is thermostable, displays good activity and acts as a highly chemoselective 4-n-propylguaiacol oxidase. We lastly use our engineered biocatalyst in an illustrative preparative reaction at gram-scale. Our findings show that a natural enzyme can be redesigned into a tailored biocatalyst capable of valorizing lignin-based monophenols.

Date: 2022
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DOI: 10.1038/s41467-022-34912-3

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