ArticleNature communications2022
Structure- and computational-aided engineering of an oxidase to produce isoeugenol from a lignin-derived compound.
Article in Nature communications, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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13 citing papers in PubMed, 39 citations in OpenAlex.
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- Synthesis of novel derivatives from machilin C/D as antiproliferative agents against triple negative breast cancer.European journal of medicinal chemistry reports · 2025Article
- Structure-function relationships in unspecific peroxygenases revealed by a comparative study of their action on the phenolic lignin monomer 4-propylguaiacol.Biotechnology for biofuels and bioproducts · 2025Article
- Transforming a Historical Chemical Synthetic Route for Vanillin Starting from Renewable Eugenol to a Cell-Free Bi-Enzymatic Cascade.ChemSusChem · 2025Article
- Surface display of eugenol oxidase and dioxygenase complex as a sustainable biocatalyst for efficient bioconversion of lignin-derived 4-n-propylguaiacol to vanillin.Microbial cell factories · 2025Article
- Widespread distribution of BpfA-mediated bisphenol F degradation among members of the Pseudomonadota and Actinomycetota.The ISME journal · 2025Article
- Catalyzing the future: recent advances in chemical synthesis using enzymes.Current opinion in chemical biology · 2024Review
- Benzenoid Aromatics from Renewable Resources.Chemical reviews · 2024Review
- Substrate scope expansion of 4-phenol oxidases by rational enzyme selection and sequence-function relations.Communications chemistry · 2024Article
- A comprehensive review of eclectic approaches to the biological synthesis of vanillin and their application towards the food sector.Food science and biotechnology · 2024Review
- Engineering Enzymes for Environmental Sustainability.Angewandte Chemie (International ed. in English) · 2023Review
- Engineering Enzymes for Environmental Sustainability.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2023Review
- One-Pot Biocatalytic Synthesis ofACS catalysis · 2023Article
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Authors and funding
9 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
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.
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