8BAP

Eugenol Oxidase (EUGO) from Rhodococcus jostii RHA1, eightfold mutant active on propanol syringol

Summary for 8BAP

• Entry DOI: 10.2210/pdb8bap/pdb
• Descriptor: Probable vanillyl-alcohol oxidase, FLAVIN-ADENINE DINUCLEOTIDE, 4-[(1E)-3-hydroxyprop-1-en-1-yl]-2,6-dimethoxyphenol, ... (5 entities in total)
• Functional Keywords: biocatalysis, lignin, fad, flavoenzyme, oxidoreductase
• Biological source: Rhodococcus jostii RHA1
• Total number of polymer chains: 16
• Total formula weight: 958806.54

Authors

Alvigini, L.,Mattevi, A. (deposition date: 2022-10-11, release date: 2023-10-25, Last modification date: 2023-12-13)

Primary citation

Guo, Y.,Alvigini, L.,Saifuddin, M.,Ashley, B.,Trajkovic, M.,Alonso-Cotchico, L.,Mattevi, A.,Fraaije, M.W.
One-Pot Biocatalytic Synthesis of rac -Syringaresinol from a Lignin-Derived Phenol.
Acs Catalysis, 13:14639-14649, 2023

PubMed Abstract: The drive for a circular bioeconomy has resulted in a great demand for renewable, biobased chemicals. We present a one-pot biocatalytic cascade reaction for the production of racemic syringaresinol, a lignan with applications as a nutraceutical and in polymer chemistry. The process consumes dihydrosinapyl alcohol, which can be produced renewably from the lignocellulosic material. To achieve this, a variant of eugenol oxidase was engineered for the oxidation of dihydrosinapyl alcohol into sinapyl alcohol with good conversion and chemoselectivity. The crystal structure of the engineered oxidase revealed the molecular basis of the influence of the mutations on the chemoselectivity of the oxidation of dihydrosinapyl alcohol. By using horseradish peroxidase, the subsequent oxidative dimerization of sinapyl alcohol into syringaresinol was achieved. Conditions for the one-pot, two-enzyme synthesis were optimized, and a high yield of syringaresinol was achieved by cascading the oxidase and peroxidase steps in a stepwise fashion. This study demonstrates the efficient production of syringaresinol from a compound that can be renewed by reductive catalytic fractionation of lignocellulose, providing a biocatalytic route for generating a valuable compound from lignin.

PubMed: 38026814
DOI: 10.1021/acscatal.3c04399

Experimental method

X-RAY DIFFRACTION (2.3 Å)